Editor’s note: This is a guest post from Joe Weber of Dappered.com. 
First, a word on the word “gentleman.” To some, it sounds a bit snooty. Like some stuck up Victorian-looking fellow who would never get his hands or clothes dirty. But for the purpose of this article, know that the term is really in reference to that large swath of men who want to experience Las Vegas without feeling like they’re an extra in The Hangover. Y’know, the type who’d like to visit Sin City without committing sins so egregious that St. Peter has the evidence bookmarked for easy access when he finally hits the pearly gates. There are plenty of wrong turns to take in Las Vegas, and far too many dark alleys to wander down. These suggestions should help you maximize your enjoyment of America’s Playground, all while keeping at least some money in your pocket and letting you actually tell people about your trip once you get back.
Pay for your trip in advance, in cash.
Here’s how it usually goes: “Whoo hooo! Vegas trip! I’ll just put this on my credit card, and once I get back I’ll pay it all off at once.” Bad idea. If you’re planning a vacation a few weeks or months in advance, pay for it when you book it in full. That’ll leave your mind clear of any nagging financial obligations while you’re down there. And a clear mind means better decisions. You’d be surprised how many people head to Las Vegas knowing they’ve got the bill to pay once they get back, and gamble recklessly attempting to “win” their trip while they’re there. Pay for the hotel and airfare as well as any pre-planned activities ahead of time. You’ll have much, much more fun.
Arrive on a Thursday and Leave on a Monday.
A Friday arrival / Sunday departure just doesn’t leave you with enough time to relax. That, and McCarran Airport is jammed on those days. Show up on a Thursday and leave on a Monday. You’ll pay a little less in airfare and much more on hotel thanks to the extra days, but it’s awfully worth it in the long run. Want to go full maverick, and you have some flexibility in your work schedule and vacation time? Consider a weekdays only visit. The town is far from deserted, but it’ll be a lot easier to do what you want to do.
Stay in a decent hotel. Gamble less.
Men usually skimp on accommodations so they can gamble more. That’s a rookie move. Unless you’re seriously good and you go to “make” money you’re losing out. No doubt, hitting the tables can be a great time. But the house (almost) always wins. And unless you win a ton of money, your dump of a room at the Laughing Jackalope  (I stayed there before the motel closed–big mistake) is still going to wipe whatever smile off your face once you crash for the night. The amenities at the nice hotels are worth the extra cost. Access to good food, non-smoking floors, exhibits, gardens, shows, the pool, good staff, friendly dealers, a decent bed, a bathroom where a cockroach doesn’t crawl out of the roll the first time you spin a few sheets of toilet paper off it (true story)… it’s all worth it and then some. Most of us who have gone to Las Vegas more than once stay in a cheap and dirty place the first time, learn our lesson, and then cut the gambling budget for accommodations. It’s a lesson that I hope no one has to learn firsthand in the future.
Dress well. Hardly anyone else does.
And that means bringing a well-tailored suit. Las Vegas might be the only place in the world where you can be enjoying an expensive, gourmet meal in an amazing restaurant, and the table next to you is filled with dudes wearing cargo shorts and crocs. And that’s fine. They’re probably all millionaires. But you’ll be treated better by everyone if you look like you deserve respect.
Dressing your best while on vacation also makes it feel more special than it already is. You’d dress up for your girlfriend or wife if you two were having a big evening out, right? Consider this a big few-days out. No need to be dressed to the nines 24/7, but getting on the plane and hitting the hotel in something other than what you’d wear when you’re stricken with the flu makes the entire trip more enjoyable—more of an experience. You don’t want to look like you’re headed to a board meeting or court, so skip the pinstripes and double-breasted numbers. And no black suits either (you’ll look like a hotel employee). The safe play is a light grey two-button with lighter brown dress lace-ups. Wear it on the plane if you don’t want to check luggage. Bring a few bright white and light blue dress shirts, a pair of dark wash jeans, a navy cotton sport coat, and a pocket square or two, and you’ll be set for almost any situation. If it’s during any part of the year where the temps get brutal, keep fabrics light in color and weight.
Avoid getting drunk.
This is obvious for those that either don’t drink or don’t like the feeling of being intoxicated. But if you’re the type who likes to drink, know that if you don’t ACTIVELY avoid overindulging in booze, you’ll spend at least a full day if not more hungover in your hotel room (another reason why you want a nice, clean place to crash). There’s a reason why there’s alcohol everywhere in Las Vegas: the looser you get, the looser your wallet gets. Don’t get a free drink every time the cocktail waitress comes around with the freebies at the tables. She’ll bring you water or club soda. Ask for it. And if you do start to feel like you’ve had too much to drink? Get back to your room, drink some water, and get some rest. And for the love of the person who’s stuck sitting next to you on the flight back, don’t get hammered the night before you leave. If you don’t think you’re the type that gets airsick, wait till you have a pulsating hangover on a too warm flight that’s a little bumpy on takeoff. You’ll get very familiar with that little blue bag in front of you real quick.
Gambling: Be polite and tip your dealers. Even if you lose.
It’s not their fault you bet big and lost. Always save a few chips for your dealers. You’re done before you use those, because those should go to the dealer as long as they’ve been courteous. The best dealers can often make you feel like your session of losing at a table, especially if it’s an hour or so at craps, has been more than worthwhile. Show them you appreciate their work. And tip the cocktail waitress too when she comes around. Especially if she asks what you’d like, you politely inquire if she can commandeer some top shelf stuff (don’t get too greedy though), and she returns with it in hand. A $10 – $15 glass of booze at the bar can cost nothing more than a $4 tip if you treat your cocktail waitress right. Everybody wins here.
Know who else to tip.
Yes, the dealers and cocktail waitresses will appreciate the tip. But so will the doorman/bellhop in charge of getting you a taxi at the hotel, as well your cabbie, the guy who checks your bags at the airport curbside check-in, and the housekeeping staff that cleaned your pigsty of a room during your stay. It’s a few bucks here and there that can add up, but you’ll be treated much better in the long run.
Research restaurants and their menu prices.
There’s always the possibility you’ll get a bad waiter. Better to spread out your money on a few mid-level priced meals, than going all in on one restaurant only to get stuck with a snob of a server. As one awfully nice rake man once said to me while playing craps after a particularly bad experience at a particularly expensive restaurant: “Some people in this town forget what business we’re in. It’s the hospitality business.” There are bad eggs out there. Know what you’re willing to spend at a restaurant, poke around online before you go, and don’t overspend at one place.
See a show… or three.
There’s so much to see there. A blinking slot machine is as boring as it gets. Most want to gamble. That’s fine. But there’s some serious world class entertainment in Las Vegas. Set aside a night or two (or more) to NOT gamble. Get a great meal. See a show. Walk around and enjoy the lights and atmosphere. Watch the fountains at the Bellagio. Turn in knowing you won’t wake up the next morning with a raging hangover nor will your wallet have been cleared out thanks to a bad half hour at the blackjack table. Las Vegas is much, much more than what every bachelor party stocked with 23-year-olds experiences there. This, if you’ll pardon the word, “gentleman’s” approach, should leave you with no regrets (imagine that) and actually feeling like you won in Las Vegas. Even if you leave a little lighter in the wallet than when you arrived.
Joe Weber is the Director and Editor of www . Dappered . com  where affordable style is the one and only focus. He believes that living right, living well, and looking good doesn’t mean you should go broke in the process.