in: Featured, Outfit Guide, Style

Your First Style Steps: Beyond Jeans, T-Shirts, and Tennis Shoes

Man trying on clothes at store.

With our archives now 3,500+ articles deep, we’ve decided to republish a classic piece each Sunday to help our newer readers discover some of the best, evergreen gems from the past. This article was originally published in October 2019.

A lot of guys would like to improve their personal style, but they feel a little overwhelmed as to how to start. Men’s sartorial blogs and magazines often showcase photo spreads of male models wearing expensive, fashion-forward clothes that seem inaccessible and/or undesirable, and don’t point that helpfully towards a way forward.

Fortunately, taking your first steps towards upping your style game doesn’t have to be intimidating or involve making dramatic changes to how you dress. Instead, it requires only modest purchases that anyone can make with a minimum of effort and some very basic knowledge. Together, these wardrobe additions will significantly upgrade your look from the basics of jeans, t-shirts, and tennis shoes, all without breaking the bank, or making you break much of a sweat.

Think of the following items as the starter set for any well-dressed man:

1. A Couple of Plain White Dress Shirts

They may look like serious business pieces on the rack, but plain white dress shirts can go with pretty much any outfit.

You can wear them with slacks and a tie, or a suit if you have one, but you can also throw them on with blue jeans and a pair of beat-up work boots.

You want a couple of these because they’re never going to be wrong. While you figure out the rest of your style, basic white shirts hold the fort.

Point collars are a little nicer than button-downs, but the casual look of the latter will probably best fit your day-to-day style. Get ’em for $20 or so at any department store, or keep an eye out for sales online. Secondhand is fine too, so long as the pits aren’t yellowed or you’re confident in your stain-removing abilities.

Most importantly, make sure your dress shirts fit really well, checking out this full guide to how they should look and taking them to a tailor to get them altered.

2. A Casual Sports Jacket

It might not seem like a high priority if you’ve never been a jacket-wearing kind of guy, but don’t underestimate the value of a sports jacket.

This doesn’t have to be anything fancy, or even new. Secondhand is just fine — if anything, a little wear and tear around the edges adds authenticity. Look for sales or thrifted pieces and you can expect to spend anywhere between $10-$100.

Try for something simple and casual when you’re just getting started. Gray tweed or a brown tone of some kind should work well, in textures or patterns if you like that sort of thing.

Experiment with throwing the jacket on over a simple dress shirt and jeans when you go out to dinner or to a party. It’ll be a painless upgrade to your usual look — and one that’s not so dressy that it’ll rock the boat.

3. Nice Jeans

Upgrading your style a little doesn’t mean saying goodbye to blue jeans forever. In fact they’re a staple (or at least should be) in every man’s wardrobe.

So rather than ditching them, you’re going to improve the quality of your jeans. Skip the offerings from places like Target or Macy’s and head to a store that specializes in denim instead — a Levi’s or a Lee’s outlet works great. You can also shop online, where you’ll have your pick of everything from the major brands to small batch raw and selvedge denim jeans. Expect to spend a little bit here if you’re buying new — $60 is a good price, and it can go higher for specialty brands.

Find a pair you like and opt for a fairly close fit in dark indigo. These are your new “dress jeans,” for any occasion when you want to look comfortable and relaxed but still like someone who cares about his appearance.

The fit is important here. The denim doesn’t have to be skin-tight, but it shouldn’t have too much excess either. You want a little taper to the legs, and an overall more “tailored” look than the jeans you’d wear to work in the yard.

4. Casual Leather Shoes

A pair of decent shoes changes the entire outfit they’re worn with.

Swap tennies for leather footwear and you’ve suddenly got a much more respectable look.

You don’t have to spend much to get the effect. Most department stores will have leather shoes (generally with rubber soles) for around $50.

Leather footwear, of course, comes in a variety of styles, from brogues to loafers to work boots. Choose a pair based on your personal style and the formality of your outfit. Whichever way you go, they’ll be a big upgrade from sneakers.

5. A Lightweight Sweater

Sweaters are a little like sports jackets in that some guys love ’em and own about a dozen, and other guys never even think about putting one on.

Split the difference and grab one or two thin, lightweight sweaters. Solid colors are best — you’ll be layering with other pieces.

A good sweater can be a top layer or can go under a sport coat — wear that instead of a more technical-looking jacket for warmth on cool days.

Your price is going to vary depending on what the sweater is made out of, but you can get cheap knit cotton ones for around $30. Wool (especially cashmere) is going to be warmer and sturdier, but it’ll also cost more, in the $100 range for a good one bought new.

It may seem like a strange investment at first if you’re not a sweater-loving guy, but give it a try. For about half the year (in temperate climates), a plain sweater with a dress shirt under it and a decent pair of blue jeans will be temperature-perfect — and stylish.

6. A Handsome Overcoat

If you’re going backpacking or mountain climbing, bring the high-tech parkas and performance gear you need to keep your body warm. For bumming around town, however, skip the puffy fabrics, high-gloss plastics, and chunky pull-tabs of outdoors gear whenever you can. If you’re not going to be out in bad weather for hours on end, your overcoat doesn’t need to be high-tech. Rather, get a coat that’s both warm and classically handsome.

There are a lot of options here, depending on your climate and your style. Trench coats or dressier wool overcoats work well for suit-wearing men; guys who don’t have a suit jacket’s length to cover up can get away with shorter options like pea coats and fatigue jackets.

You can almost always find decent secondhand coats at thrift stores or online. Don’t pay more than $50-$75 for it unless you find one you really want; if you’re patient and willing to try some odd styles out you can probably end up spending as little as $20.

7. A Good Leather Belt

A nice belt is an accessory that can go a surprising ways towards pulling a getup together.

If you’re expecting to be wearing a business suit, you’ll need a slimmer black dress belt in your collection, but for most guys’ day-to-day wear, a brown, leather, thicker/wider “work belt” style is the real essential. The strap should be 1.5″ in width or more, and made of a natural or tan leather. The buckle should match the metals you wear (watch/rings). Here are all the details you could ever want for picking out a good one.

Don’t be afraid to invest up front in a really sturdy piece of leather. Leather goods companies sell high-quality belts for around $30-$50, and you can add handcrafted or vintage buckles for $5-$25 a pop, if you’re into that. 

Building Your Wardrobe Over Time

Take a quick look back over the estimates we made in this list and you’ll see that even the bare minimum investment is going to be more than $200. Depending on your current financial circumstances, that may seem like a lot.

But remember, this isn’t a package deal. You’re not going out and grabbing these overnight.

It’s easy to pick up one or two pieces per month, just by browsing around online and keeping an eye out for deals, or by swinging through the mall once in a while.

Many of these also make good gifts — relatives who don’t know what to get you for Christmas would probably be thrilled to hear that all you want is a leather belt or a couple of dress shirts.

Take it slow, and remember that the most important part of these upgrades is wearing them.

You’ll come to see that while the effort involved in trading in old blue jeans, a T-shirt, and sneakers, for fitted jeans, a dress shirt, and brogues, will be minimal, the difference in your appearance and the impression you make will be huge.


Written By Antonio Centeno
Founder, Real Men Real Style
Click here to grab my free ebooks on men’s style

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