What to Wear on a First Date: Your 60 Second Visual Guide (Spring/Summer Edition)

by Brett & Kate McKay on May 16, 2012 · 88 Comments

in A Man's Life, Dress & Grooming, On Etiquette, Style, Visual Guides

The Go-To: Sports Coat + Jeans/Khakis. Lighter weight cotton sport coat. While, light-colored, or checked button-down shirt. Wear a stylish accessory like a watch or pocket square. Dark denim jeans or khakis. Dark brown leather lace-up shoes with rounded toe. Always dress in layers. If it gets chilly, you can offer your date your coat. Fingernails cleaned and trimmed.  The More Casual Date. Well-fitting polo shirt or casual button down shirt. Get your hair cut the week before the date and don’t try something new with it for your date. Go with your usual routine. Choose your shoes carefully – they say a lot about you and women always notice them. Canvas shoes or top-siders. Dark denim jeans or khakis. Field watch.

This post is brought to you by Life Khaki from Haggar What’s this?

Illustration by Ted Slampyak

Have any other first date style tips? Share them with us in the comments!

{ 88 comments… read them below or add one }

1 Hound May 16, 2012 at 1:21 pm

Great, but I always find summer wear easier (simpler) then winter wear. Maybe a winter follow up for those of us living in the southern hemisphere?

2 LT May 16, 2012 at 2:17 pm

Tucking in the polo shirt is lame!

3 RippyDippy May 16, 2012 at 2:46 pm

these both look incredibly lame and straight-laced.

4 Ben May 16, 2012 at 3:01 pm

Not a big fan of canvas and high-tops. Poor support, hipster-y look, and just a little too dressed-down. Nothing’s wrong with a clean pair of sneakers that aren’t too flashy.

5 Matt M. May 16, 2012 at 3:14 pm

As some general suggestions and pointers, I think these work very well for the guy who’s not sure where to start.

I’ve gone with variations of the look on the left on lots of first dates and had a lot of success–lots of compliments from women.

Finally, I’m pretty sure that this site is aimed at guys who don’t consider “straight-laced” a derogatory term. The world could use less men who think that a thin, deep cut v-neck t-shirt and skinny jeans is a good look.

6 Aaron May 16, 2012 at 3:18 pm

I’m a big fan of this site, but this particular post just seems kinda douchey and cookie cutter to me, not to mention dated.

Oh how impressed your date will be when she looks around the restaurant and sees 3 dozen other dudes with the same fresh haircut and tucked in polo shirt.

7 DROC May 16, 2012 at 3:22 pm

Watches are designed to be worn on the left wrist. Other than that, great guide.

Completely agree with Matt M, low-cut tops are made for women with big boobs, not for men.

Aaron, 3 Dozen other people in the same restaurant are probably not reading this site.


8 Okierover May 16, 2012 at 3:25 pm

I see your graphic with the ROUNDED TOE. Hear hear!
The shoes I’ve seen on websites lately are HIDEOUS! Duck foot looking square toes? Gag.
Which sets me on this tangent. I’ve been looking for leather soled dress shoes that are made in America.
MADE IN AMERICA. I’ve found some Allen Edmonds I like, but they cost more than I paid for my first two automobiles COMBINED. I can’t bring myself to buy them.
I have one pair and take ridiculous care of them for fear they will be ruined and me out 300$(US).

9 Teresa May 16, 2012 at 3:30 pm

Guys, it’s not what you like to wear but what we ladies like to see you wear.

For me, my eyes perk up when I see a man in a crisp white buttoned shirt, cuffs rolled up, clean crisp jeans that FIT at the waist and are the correct length and either cowboy boots or dockers.

10 Rhett May 16, 2012 at 3:36 pm

Aaron- Care to explain why the looks suggested are douchey? They weren’t suggesting Affliction shirts or V-neck t-shirts. And as far as your complaint that they’re cookie cutter, what else do you suggest? T-shirt and jeans? That’s soooo unique. Clown costume? Tuxedo?

And in regards to the jeers at tucking in your polo, it’s perfectly acceptable and in some cases is actually called for. Tucking in your t-shirt? Only if you’re doing PT in the army.

11 Nick Rosaci May 16, 2012 at 3:37 pm

I love the hater comments that are already showing up. I used to be that guy. Now most of the women I’ve gone out with in the last year or so made it to at least the third date–any that didn’t make it that far were my choice, and not hers. Proper dress really does make a difference! Until guys figure that out, they can keep wondering why she says “I just didn’t feel any chemistry” while he keeps showing up in a t-shirt and shorts and ragged-out running shoes.

These are classic, TIMELESS styles. Shorts, loose jeans, t-shirts, sneakers, etc., are breaking rules about how to be seen in public. Scoff at the “douchey” rules, while saying you’re far above them, huh? Most of us aren’t athletic people, yet we wear athletic wear to head to the bank?

Okie, look at used Allen Edmonds on eBay. I just bought a pair of Park Avenues in GREAT shape for $30! If you shop at the right time, you can find similar deals; that model usually goes for close to $100 used.

12 Jacka May 16, 2012 at 3:47 pm

I think a lot depends on your age, the type of the girl your going out with and the general theme/atmosphere of the date, not to mention local trends etc. While things like these can be ‘timeless’ to some, it can make you seem out of place and too much of a try hard to others.

13 Okierover May 16, 2012 at 3:59 pm

Well put Matt M.
If you group men by 5 year increments, you will see a definite pattern to the clothing they wear. Each will wear what is “cool or accepted” by their population.
Like my son said to me, “Eddie Bauer is like American Eagle for old people right?”
I said, “you nailed it son.”

14 Okierover May 16, 2012 at 4:03 pm

Thanks Nick.
I don’t know why that didn’t occur to me.
I buy my blazers on eBay. I bought a couple for less than 30$ shipped and had my local tailor adjust them for me and was out less than 60$ for a 250$ look.

15 Romarium May 16, 2012 at 4:06 pm

So, I have been a huge fan of what I have been calling the “updated Angus Young”, I put on a pair of jeans, can be worn out, destroyed, whatever, with a black belt and a T-shirt, often starkly at odds with the dress shirt that goes over it, and a tie that is tied with the schoolboy knot, and left loose so my shirt underneath shows, shoes are optional, and I get tons of compliments, and the women seem to dig it, its casual, but not, and the ties look great

16 Dede May 16, 2012 at 4:23 pm

The outfit on left is totally appropriate and tasteful for a casual date. The one the right is not. A polo without a jacket or sweater and sneakers is sure to make any woman wince and question her own judgement…let alone your maturity.. Unless you are in high school, consider option #1. Opt for cooler instead of the picnic basket…leave the basket carrying to us.

17 Leah May 16, 2012 at 4:32 pm

I’m with Teresa, it’s all about what the ladies like to see you wear! A man who shows up like the man on the left (as long as his clothes are stylish and fit well!), looks mature and masculine and confident. Mmmm, yummy. I can think of few first date situations where that wouldn’t be a good way to go. And as far as cookie cutter….dressing up makes you an independent rebel! Most guys look like slobs. Nothing more cookie cutter than looking like a slob.

But guys please don’t listen Dede…if a guy wore a jacket with a polo shirt on a picnic, it would just be too uptight. Ew. And a girl who would want you to wear a jacket or sweater on a picnic is bound to be weird. You should consider what is appropriate for the situation.

Oh one more thing that’s not mentioned…don’t put on too much cologne!

18 C.B May 16, 2012 at 5:03 pm

Any of you “men” who’ll sit there and say a tucked shirt is lame are far too proud of being slobbish little boys. If you’re going to put on a button down or polo, wear it right. Here’s why:

1. You don’t your shirt hem blowing all over the place, getting in the way and caught on things.

2. Tucking lets you show off your nice belt, as well as your butt (yes, women do look….).

3. Untucked shirts will make you look like a square, literally, unless they’re too small for you. Tucking shows your waistline, which will make your shoulders appear broader (thus more manly and appealing) than going untucked. And even if you don’t have broad shoulders, a tucked shirt will keep your body from looking like a stuffed tube sock.

4. Every bro and other douchebag these days refuses to tuck their shirts, break yourself away from those losers.

19 James May 16, 2012 at 5:29 pm

It seems like all these fashion tips are for guys who are entertaining this weekend on their yacht or at their beach house. Or for 35 year-olds. I don’t think many guys that rich or old need a lot of help.

20 Kevin Hall May 16, 2012 at 5:38 pm

I used to date all kinds of girls in high school and I would wear my skinny jeans and a plaid untucked shirt or a plain t-shirt with a hat. Now I date classier women and tuck my shirt in, match my shoes to my belt and get my clothes tailored. Looking dappered > what you wore in high school and college. Then again, if 90% of guys continue dressing like slobs, that just means my chances continue to be better! So forget I said anything. And don’t look at the above illustration.

21 unclesam May 16, 2012 at 5:40 pm

So I can´t rock my Jordan´s on dates? :(

22 Nick May 16, 2012 at 6:15 pm

There’s a difference between having a million dollars and looking like it. It’s not about being rich at all. I really like Kevin’s comment. Leave the classy women to those of us who know how to impress, then!

You can tell which guys commenting date very un-classy women who think the weekend is about going downtown and downing shots until she’s plastered and goes home with the first guy offering to drive her there, and the guys who have a woman they can take anywhere.

If you want bro-esque styles, go to a bro site. You come here for class.

23 Nick May 16, 2012 at 6:16 pm

Well, if those guys can even keep a date at all. I tell you, the moment I decided to bump up my style, I haven’t had a weekend to myself!

24 Daniel May 16, 2012 at 7:20 pm

Nick, I’ve thoroughly enjoyed reading your comments against those ragging on the illustration and what it’s supposed to *represent.*

I can say that dressing nicely has been a rather fast change for me (within the last 3 or 4 months have I decided to go after it…after 22 years of not). And I can’t agree more that you’ll get FAR FAR more looks from a white button up, cuffs rolled up to the elbows, tucked in, nice belt (Johnny Cupcakes grey), black pants (super old American Eagle cottons), and any pair of shoes that doesn’t have a fucking swoosh on them.

And get this: just today, I was at a men’s designer consignment shop and picked up a pair of slick grey Banana Republics for $21 and then just now a pair of like new size 7 Florsheim Wingtips for $15 on ebay.

Can you say, “time to impress the ladies” any faster?

25 The Dutch Dastard May 16, 2012 at 8:04 pm

Great discussion all! And very nice to see that style is not dead. Just to bump it a bit: Ladies, when you say ‘it’s all about what the ladies would like to see you wear’ i could not agree less. If she is not comfortable with what i like to wear on a date, chances are she’s not the girl for me, as my clothing represent ME, not her.
Just for the record, i’m the guy on the left. And then go left some more. Too many times have i encountered women who’d rather see me in a t-shirt and sneakers, and i’m just not down with that.

By the way, what’s with all the button down shirts? What’s wrong with a dress shirt?

26 Gary V May 16, 2012 at 8:21 pm

Call me a douche all you want, I’m still tucking my shirt in.

27 Vincent May 16, 2012 at 8:22 pm

I think men’s style is supposed to be pretty uniform. If you dress nice, your date doesn’t care that you look like other handsome men. I’d rather be just another handsome man on a date than a stand-out slob.

28 Bill May 16, 2012 at 8:23 pm

ALWAYS tuck in your shirt.

29 Vincent May 16, 2012 at 8:23 pm

Obviously these are guidelines and not absolute rules. Whatever works in a given situation.

30 Matthew May 16, 2012 at 8:36 pm

LOL. I can definitely understand the idea of dressing comfortably and for her….buuuut let’s try to be a little less selfish on the first date. This is a courtship, not a court-order. She doesn’t HAVE to stick around if she does not thinks you are visually attractive.

Consider this; MOST guys would not refuse to buy flowers for the woman on the basis that we do not normally buy flowers when we go shopping. Think of your clothes as wearable flowers. Pick out clothes as you would her flowers. Match the colors, pick styles, shades and shapes that are complimentary and that she prefers.

I think that the quicker we understand this concept, the more women you will attract.

By the way, those shoes she’s wearing probably aren’t comfortable, yet she’s wearing them. She’s not stupid. She figures that guys will like the way she looks in them, so she wears them. Do you think she goes to yoga or the gym in that? Probably not.

31 steve May 16, 2012 at 8:53 pm

How about shoes with a small metal buckle on them? I wear these every day to work, they rock.

Also, why dark denim? Do they just look better or is there an actual purpose?

32 John May 16, 2012 at 10:24 pm

Guys, If a lady thinks that wearing a coat and button down shirt is “up tight” for the nice meal that you are most likely treating her too, then you should most likely reconsider your choice of female companionship. Secondly, to those who mock the examples given above, looking like a high school dropout/ moronic hipster will, 98% of the time, attract women with similar standards.(e.g. the deeper the V on that snarky shirt = the less likely your date will be able to string together a cohesive conversation on any topic other than the Kardashians.” On a side note… Please forgive me AOM and readers for uttering that name on this site. It was intended for educational purposes only.

33 minuteman May 16, 2012 at 10:55 pm

Good info, on the whole accurate. I am not big on the whole sports jacket and jeans thing. Nothing wrong with the sports jacket, just not with jeans. Every man should have at least one good suit. We don’t all wear one a work any more, in fact I wear coveralls at work. But own a good suit, know how to wear it properly, and go on dates wear it is appropriate wear. “Every girls crazy ’bout a sharp dressed man”.

34 Nicks May 17, 2012 at 12:05 am

Good comments by most!

Personally I wear a sport coat with my nice slim straights for fall/ winter dates, usually with a nicely colored collared shirt and my wurking stiffs keeping the collar in check

For spring and summer I have a lighter jacket I’ll wear out at night but during the day a good casually button up and khakis are a good fit, in summer I’m thinking beach and outdoors, unless you got a good light jacket, skip it! Even the classier women will think you are too dressed up if it’s beautiful out or hot.

If you got a body like a model, go with the polo or tshirt on a casual day date, any man in a thirst out at night better be at a sports bar or at a beach bar

35 Raul May 17, 2012 at 1:32 am

when I go to dates, I usually go for a shirt which can be seen as something slightly elegant, but can be worn with jeans, as my shoe of choice I usually go for inside out leather shoes, which complement my look perfectly

36 Ryan F May 17, 2012 at 2:43 am

The first guy looks great but I can’t help but think the second man looks kind of tacky. I’m sure this vary’s by region but I live in a state where it constantly rains so my association with the polo is middle aged tourist/golfer, not exactly the kind of image you want to convey as young gentleman on a date.

37 John May 17, 2012 at 3:15 am

Hi Doll! Like my pocket square? It’s keen!!

38 Pam May 17, 2012 at 7:58 am

I date men in their 40s and 50s and one thing some seem to forget is the whole hair in odd places thing.. Nose ears back of neck grey chest hair … And beyond…
Make sure all of that is gone and If you can’t see well enough to groom it away– get a magnifying mirror!!!!

39 Peter Samuel May 17, 2012 at 8:23 am

Just no. Never wear dress shoes with a rounded toe. Just don’t do it. Ever.

40 Peter Samuel May 17, 2012 at 8:29 am

I guess that’s not fair, I assume rounded equal square, although I guess it could also mean pointed (which is correct and not ’80s).

41 Alex May 17, 2012 at 8:51 am

I like the basket in the casual outfit. Never thought of that. Yep, I’ll definitely buy myself a basket so as to impress my next date. Who knows when it may come in handy.

42 Daniel May 17, 2012 at 8:55 am

Eh. Seems a bit formal to me. Though I don’t think I ever tucked my polos in, ever.

But for generic advice, I guess it’s okay.

Two things come to mind about. First, whatever it is you wear, you got to be confident and cool about it. There’s no use to a sport jacket if it makes you feel bad or uncomfortable. And second is that everyone has their personal style. If you find a way to blend in the things that you like while still looking good, that’s a plus. Being genuine goes a long way. Dressing with someone’s else style might give away signs that you do not intend. This is somewhat hard to put on words, it’s a matter of taste and feeling.

I don’t really know why, but as of late I somewhat started to appreciate a more casual look. A dark green T-shirt, some not ugly-looking jeans and a brown Adidas can look pretty good if you put some effort into it. Dating should be fun, I would like to be formal doing other things. But this too depends on a lot of things. I’m young and somewhat fit. If you are middle aged and have a beer belly, it this might not fit you so well.

Taste, man, taste. Brett (and Kate), you might wanna try “A guide to good taste” or something among those lines. Fashion material for men is mostly metrosexual and/or gay these days. No prejudice intended.

43 Samuel Warren May 17, 2012 at 10:05 am

This is what I love about men’s fashion. For those wondering about winter wear: Left side simply exchange the cotton sports coat for a nice dark tweed jacket instead. On the right just add a nice sweater (with sleeves).

44 Moeregaard May 17, 2012 at 10:59 am

The guy on the left looks like Alan on “Two-and-a-Half Men.” No amount of grooming will compensate for that “Please like me!” look. Kidding aside, dressing badly means you only date trash. Dressing well opens up an entirely new realm–and you can still date trash when you want to.

45 Phil Haney May 17, 2012 at 1:27 pm

Nice to see a Lefty once in a while!

(Mr. Casual Date has his field watch on his right hand)

46 Nihilyst May 17, 2012 at 2:29 pm

I think the most important thing would be to just wear something you’ll be comfortable in. Something loose if you’re the nervous type. If you already know the person they are probably ok with your style so there isn’t much of a reason to go over the top. Use some sense and dress for the occasion. I’d worry more about my date than what I was wearing.

47 Ryan May 17, 2012 at 3:26 pm

Love both these looks. I dress like the left one in my daily life sometimes and am told I look like a professor.
I find that with this or any style you use on a date is that it’s all about the details. I throw on a watch because it looks good and its better to check the time on it then pulling out your phone on a date. My girlfriend now notices when I DON’T have a watch or other accoutrements on.

48 Aubree May 17, 2012 at 4:11 pm

I see there are a lot of people disagreeing. But it’s simple, women like clean, and the men are dressing like slobs lately. Saying goodbye to that look for a night out isn’t a bad thing.
My husband is a good looking man, and has his own style white v neck, jeans, and cowboy boots. But for this job we did last week required this “casual” look. I’m not saying I like tucked in polo’s or canvas shoes, but honestly he looked polished, and yeah, it got my butterflies going. Dressing up for a date is lost by many men, so whether this advice is “straight laced” it’s good advice to start dressing up for a date. And I’m not talking about looking like those jersey boy douche bags that love their dress up time, all bronzed with their tattoo t-shirts, probably reeking of cologne. [Women’s sense of smell is better, a dab will do ya!] It just looks greasy. I’m talking about cleaning up like a man. If I saw my husband get dressed up in either of these outfits, I will make sure his efforts were worth it.

49 Logan May 17, 2012 at 5:19 pm

@DROC- It is actually more common to wear a watch on your non-dominant hand. Therefore if someone is right handed, they should wear it on their left wrist and vice versa.

50 FatAlbert May 17, 2012 at 7:00 pm

For me it is my big johnson T-shirt tucked into my stranglers, with a woven belt and cowboy boots

51 Spencer Hoge May 18, 2012 at 12:26 am

I have always had a huge problem with style guides for men because it’s always like a jacket and pants of some sort… I would never wear any of these because it’s summer, I live in the deep south, and I’m a thorough-bred Northern European… I can’t walk around the block in gym shorts and a t-shirt without sweating profusely. This would never work for me, not even for a movie date. Getting out of the car and into the theater would make me sweat like hell. I have to opt for shorts out of necessity; look good and sweat bullets/ smell bad, or wear a pair of dockers shorts and a shirt and avoid the hellish summer heat. And before people say I need to try different materials for my pants, just no… That stops working around 75 degrees for me. 90-110 and shorts are a must.

52 Andrew May 18, 2012 at 1:27 am

Haha, too bad I’m not gonna need this for a while. :P

53 Frank May 18, 2012 at 2:28 am

Completely agree with Spence Hoge. Down here in Texas, you can’t wear long sleeve button down shirts from May-October unless you don’t have any sweat glands on you. I am 28 and am a combination ectomorph/mesomorph with a nice build. I typically wear your basic regular v neck t-shirts, as I have a short neck, and some nice denim matched with whatever designer tennis/high ankle boots I feel look appropriate for the environment I will be in. I don’t typically frequent swanky joints so I’ve done well with what I’ve gone with. It all comes down to what you’re comfortable with and what actually looks good on you, not what someone else thinks will look good on you. Trial and error gents, trial and error.

54 Dakota May 18, 2012 at 3:35 am

DROC, not all watches are designed to fit on the left wrist. Say, what about the left handed people such as myself and most likely a few other gentlemen here? Seriously go look. I happen to own all left handed (right wrist) watches. Invicta nonetheless.

55 Dakota May 18, 2012 at 3:36 am

DROC, not all watches are designed to fit on the left wrist. Say, what about the left handed
people such as myself and most likely a few other gentlemen here? Seriously go look. I happen to own all left handed (right wrist) watches. Invicta nonetheless.

56 Nick May 18, 2012 at 9:02 am

The author of most of the style articles on this site is from Texas. He definitely approved of this visual. If anyone knows how to dress warm in the heat, it’s a professional clothier that is from a warm climate.

And sorry Spence, but I’m about to say exactly what you didn’t want to hear. If you’re wearing anything with any kind of synthetic in it, especially polyester, you will feel stuffy and hot. If you’re wearing cotton (it has to be light) or linen, it can actually do as good, if not better, a job in keeping you cool in the sun. A v-neck shirt is designed to be an undershirt. This is not “swanky” style. It’s casual. There are a few more levels of formality that go above the sports coat and jeans look.

I live in Florida, and the humidity here will kill you. I have a few polyester short sleeve shirts, and a few light cotton long sleeve shirts. Guess which are cooler? I actually wore one of the poly shirts a few days ago and was walking around downtown Orlando, and could feel the heat billowing out of my sleeves. It felt like a hair dryer. I was essentially wearing a short sleeve plastic bag. Yes, fabric does matter.

And Dakota, I’m curious; left-handed watches? I thought all you had to do was put your watch on your right hand, and there you go. While I’m thinking about it, I guess it means that the dials are on the opposite side of the face, but I had no clue there was such a thing!

57 Nick May 18, 2012 at 9:03 am

And by the way, I have a first date tonight. I’m going with the tried-and-true guy on the left. Like all of my dates in the last year, this date will go very well, and she’ll agree to a second date.

58 Gwen May 18, 2012 at 9:57 am

I don’t think I have ever noticed the shoes a guy was wearing, unless he was wearing big stompy goth boots. And even then, only when they’re really obvious ones like New Rocks.

Otherwise, right on though.

59 Gwen May 18, 2012 at 10:05 am

Also, having read some of the previous comments… a tucked-in shirt is a very good thing, assuming you’re in good shape. It shows off your bum, and the shape of your back. (Which is a nice powerful V, right guys?)

Black polo shirt tucked into jeans with a plain belt is one of the most flattering casual outfits I’ve ever seen on a fit guy.

60 Vincent May 18, 2012 at 6:41 pm

You worry about what your wearing because not only does a woman care a lot, but its one thing that you can do more objectively correct. You and your date may not connect over conversation, but at least you wore the correct outfit. If you couldn’t do that, you were lazy or ignorant on the easy part that you got to plan ahead. In today’s challenging social environment, it’s best to cover as many objective bases as possible with absolute rules. By objective, I mean very close to objective. A man may as well be perfect in as many ways as possible and not sweat were this is impossible.

61 Diane May 19, 2012 at 11:01 pm

What makes the guys in the illustration look cheesy is their grins, the wave, and the illustration style. The clothing choices are fine! A lot of the criticism comes from men, and most of the women commenters are approving. If you’re dressing for a date, get your opinion from women, not men (obviously).

Speaking as just one woman, though, I am utterly sick of khakis. Dark pants–or anything but khaki–are so much more flattering to anyone. Why is khaki so popular? Once I looked around a room in a crowd and more than half the men were in some kind of khaki…6-8 of them. And in my opinion, khakis only look good with white. I never understand why men pair them with a light blue or blue striped shirt. But I’m probably in a tiny minority about all this, because what I dislike is SO common…so feel free to ignore me. ;-)

62 Trucker Red May 21, 2012 at 8:18 pm

I will not leave wear a shirt untucked outside of my house. Or inside, usually. Good attire for a first date, IMHO (though I’ve been married for many years now, so take it with a grain of salt):
Decent lightweight sportcoat
Oxford shirt, worn tucked in with the collar unbuttoned, with a T-shirt underneath. Sleeves up or down, as desired.
Jeans or khakis
Tasteful footwear (loafers maybe, or perhaps regular clunky round-toed lace-ups…a decent pair of cowboy boots might also work). Also make sure the shoes and belt are the same color.

63 Allen Uribes May 23, 2012 at 1:10 pm

@Nick I absolutely agree with Spencer Hoge. You are correct that fabric matters, but as Mr. Hoge said only up to about 75 degrees Fahrenheit. I’m in the Houston area and have been for most of my life (age 22). During the summer it is absolutely way too hot for anything that is long if you are to be outside for more than five minutes. I completely understand if someone walks to lunch during work hours, and they have to endure the heat in their trousers. That makes sense.

However, if not at work, do yourself a favor and get into a pair of shorts. I have light cotton chinos, medium-dark denim jeans, 100% cotton long sleeve shirts (rolled up with top two buttons unbuttoned) and I will still sweat like a dog outside. By the way, the pants don’t cover my shoes, they sit right at the top when I’m standing up straight.

For those who say shorts look childish or ridiculous or anything else negative, I invite you to come to Houston between May and September and spend five minutes walking about outside with your pants and long sleeve shirt…tell me just how comfortable you feel in that.

As far as a date at night, the guy’s outfit on the left can be done and I would certainly do it although not so comfortably.

64 HurricaneDave May 24, 2012 at 3:44 am

I think a big thing here that hasn’t been adressed but what this all boils down to is “consideration” which is displayed by “effort.” Your date is going to take one look at you and immediately know whether or not you put any effort into dressing yourself for the date which in turn is going to tell her your amount of consideration for her. Let’s be honest, part of her agreeing to go on date with you rested on her considering how she would look to be seen with you in public (and don’t cry “superficiality” here because hell, part of you asking her probably rested on it as well) At this point, you’ve at least won that battle because she said, “yes.” If you show up looking like you don’t give a sh*t though, that tells her that you don’t give a sh*t about her and she’s not worth your effort. It does NOT tell her that you are “real” it tells her that, to you, she wasn’t worth it. She’s not going to react well to that becasue she now has to be seen in public with someone who is indirectly stating to everyone who sees the two of you that “she’s not worth it.” What the ladies have said here has truth. It’s what the ladies like to see you wear. The arguments that you have to feel out the situation and that she should accept you for you have validity as well. The statements are all sometimes right and sometimes wrong with plenty of grey between them. What will always remain constant though is that what ladies like to see you wear is something that says you put some thought into how being seen with you will make her look. That you put the effort in. If you’re going out with her, isn’t she worth that anyway? Unless you’re only worthy of cheap women I’d say so.

65 Allen Uribes May 24, 2012 at 4:39 pm

@HurricaneDave I definitely agree with you; there are lots of gray areas but showing you put forth effort in your dress reflects directly on your view of the woman or man (not everyone is heterosexual).

66 Josh May 27, 2012 at 5:15 pm

This is a great guide.

67 Michael May 28, 2012 at 3:01 pm

Both the author of the guide and several of the posters have demonstrated that most Americans don’t understand what the term “button-down shirt” means. It means a shirt with a collar that buttons down to the body of the shirt. The author and the posters are apparently using it to mean a “shirt fastened down the front with buttons” (i.e., what used to be known simply as a “shirt”).

68 Josh May 28, 2012 at 6:26 pm

The only thing I would change is I wouldnt tuck the polo shirt in. Otherwise great guide.

69 Odessa May 28, 2012 at 9:22 pm

I would prefer if my date were to keep himself looking tidy and aware of his physical appearance in public, not just for me, but for himself. People DO, despite all of us wishing others would judge us for our personalities, make first impressions that focus on how another person is dressed. It’s just how we work, and that’s how it is in all cultures and societies.

It doesn’t matter what culture or subculture you’re a part of—the way you dress is a part of what kind of impression you want to give people. If a man walked up to me with wrinkled pants, shirt untucked, worn sneakers, and I was supposed to start my first date with him, I would be disappointed. I’ve made an effort to dress nicely, to make sure I look nice, smell nice, and all for him, and he’s dressing like he’s just going over to his friend’s house to play video games. Not the same situation.

Now, if I was waiting for a man to go on a date with, and he walked up to me with a simple polo shirt, dark pants, nice shoes; cleaned up and smelling good, I would swooooon, haha. Yeah, it sounds so simple, because it really is that simple. Look polished, and a woman will take that into a lot of consideration.

The casual look in that illustration reminds me a lot of a professor I used to have in college. He was an older man, maybe in his forties (I’m in my late twenties right now), but he dressed like that all the time. He was always well groomed and carried himself so well. And despite his age, the way he presented himself made a big difference in how the younger female students viewed him. Let’s just say he had a lot of lady admirers. lol

I’m not advocating older men dating younger women here, or student/professor relationships; I’m simply proving my point. If you think that these looks above are “lame,” “boring,” “douchey,” then you’re missing the point completely. Even if you’re a part of a subculture that doesn’t associate itself with these kinds of clothing at all, you should still be able to take these examples into consideration and incorporate them into your style for the sake of presenting yourself in a respectable manner. On a date, it takes two to tango, and if the lady is doing all the work while the man is making little effort to impress, then that guy doesn’t deserve her, and she deserves better.

70 Toby Crow June 1, 2012 at 10:54 pm

Very impressed with the dialogue that’s going on here. Also, an eyebrow was raised after noticing all the women posting. Our manliness sanctum has been breeched I’m thinking.

71 JM June 2, 2012 at 9:01 pm

I don’t think its very manly dressing simply to impress the girl – its like saying “In order to be secure in myself, I need you to like me.”

72 Nick June 5, 2012 at 5:46 pm

For a casual date, wear a nice fitting polo and match whatever logo or emblem’s color on your polo with your undershirt. Make sure you hair is nice, wear jeans with a belt that accents your outfit, and nice gym shoes (I wear a pair of fresh nikes). I’ve never gone wrong with this.

73 Rebecca June 7, 2012 at 2:29 pm

As a rule of thumb, the younger you are, the more casually you dress. A tucked-in polo would be too much for an 18-year-old, but you risk looking immature if you’re in your 40s and you show up in a graphic tee.

Individual preferences play a huge role in this. I can’t speak for all girls, but I like a guy who doesn’t put a huge amount of time or money into his appearance. To me, it just comes across as shallow, self-obsessed and wasteful, especially if you’re obviously just following trends.

At the same time, girls obviously do put quite a bit of effort into their appearance and a guy who shows up, unshaven and bedraggled, in a ragged, smelly, ketchup-stained t-shirt, is unlikely to please anyone. Especially if you ever have the misfortune of dating a fashion designer.

74 Trent June 10, 2012 at 9:25 am

So as the drawings may look very cheesy, I found this very helpful. The feild watch was alittle over the top but in any case there will always be a difference in style. Here on the left with the man in the blazer and khakis I think a nice dinner watch would be a great placement on the wrist but like I mentioned difference in style. As far as anything goes I may be looking fly for my first date with a lovely women in a great setting. Thank you Art of Manliness.

75 chris June 14, 2012 at 12:19 am

sorry ben, sneakers are for the gym only

76 Pecos Bill June 15, 2012 at 12:27 am

This article has the same go-to outfit! http://bit.ly/9uWMUf

77 Muaz Abd Hamid September 23, 2012 at 11:04 pm

it reminds me to men in black 2……

78 Judson Carroll October 30, 2012 at 5:23 pm

I always have trouble finding kakis or casual dress pants that fit well. I notice Paul Ryan wears some very good looking pants. They fit well – not loose, not tight… just right. Anyone know what label or style he wears?

79 Kate December 31, 2012 at 5:43 pm

I think that as long as a guy’s face looks good, they’re fine. Jeans preferred over shorts, and bright colored lace sneakers. Just no graphic shirts
Ima lady who likes classy men, don’t be a douchebag

80 Sam February 6, 2013 at 3:51 pm

No denim on a first date.

81 chrissy February 16, 2013 at 3:29 pm

I love this! a place where men can get tips and blog about it. From a womens prospective a dark denim is a must unless going somewhere very upscale. Recently went on a date with a guy who 1. did not cut his hair. 2. wore converse. 3. wore light colored jeans (wide leg/cuffed at the bottom)… Needless to say no second date. I may just txt him to refer to this page lol

82 Robert February 19, 2013 at 4:24 pm

Think about it this way (and this has been hinted in previous posts). A woman puts a great amount of time, effort, and detail into looking her best before going on a date. She wants to look good for you, and by that accord alone you should give her that reciprocal respect. Dress like a gentleman. Failing to groom yourself properly displays that your time is more important than hers and that’s a sour impression.

83 Rooster March 6, 2013 at 10:16 pm

My go to: t-shirt, nice fitting pair of jeans and shit kickers. The other styles don’t fit my personality. I leave the chain wallet at home unless I’m riding my MC. I also put a little extra smell good on.

84 Rooster March 6, 2013 at 10:22 pm

Judson, He gets those custom fitted. If you have the money that’s the way to go. I personally can’t pull off khakis unless I want to flash back to the days of JENCO’s and Airwalks so I stick to jeans.

85 Redekod April 17, 2013 at 8:37 pm

Hi, I think that jeans should be off the radar immediately when it comes to dates. Khakis or other slacks are the way to go for dates 100%. Also what happened to neckties? How about a tie and sweater vest combination?


86 Bob May 18, 2013 at 7:46 pm

I went for the more casual date. Long story short im not single anymore.

87 Stephen September 18, 2013 at 12:00 am

Both of these looks while nice do not work at all for hot climates like Florida… especially if your car does not have air conditioning like mine…

Also, while both of these looks are quite classy, keep in mind the kind of girl you’re going out with. The kinds of girls I tend to date would probably rather see me in my skinny jeans with my converse sneakers and either a nice stylish shirt or a band t shirt for a casual date. Of course for a more formal date I enjoy being able to go all out and wear a coat and tie.. know your venue… also at least in my group of friends polo shirts outside of a semi-formal situations tend to say, “I’m a stuck frat boy that just wants to get drunk and get in your pants.” For the record I am in a fraternity (Phi Mu Alpha Sinfonia) so don’t think I believe all members of frats are like that… its the the stereotype I’m referring to. Because of those reason (the weather down here, my social group, and what certain styles of dress mean to us) I would most likely dress completely differently for a casual date then what this suggests.

88 Stephen September 18, 2013 at 12:12 am

After reading some of these comments I feel I need to defend both my honor and the honor of the kind of girl I often date. Just because I feel comfortable in a v neck t shirt and skinny jeans does not mean I am a slob or un-manly. I put thought into what I wear and just because I don’t look like a business man or a lumberjack it doesn’t mean I’m not manly. I happen to be a young musician (that is also my job) and I feel its appropriate for me to dress as such. Even if I wasn’t a musician, if I choose to dress that way and put thought and effort into it, I can still look just as nice and handsome as a man in a pair of khakis and a dress shirt, and the kind of girls that I go out with tend to find they way I dress attractive. And before you say, “all they want to do is go downtown and get drunk and go home and jump in bed,” you need to watch yourself. I do not waste my time with girls like that. The girls I spend my time on are wonderful beautiful young ladies that love and honor God. Many of them love music, literature, and art. Just because a person dresses like a punk or rocker or whatever doesn’t mean they’re immature and not worth your time, and for people like them, that can much more attractive then some polo shirt routine.

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