Rule # 1 (the only rule that can’t be broken): Your clothes must fit!
Over-sized clothing has only ever been appropriate once: When Chris Webber and the rest of the Fab Five stormed to college basketball immortality (and later infamy) at Michigan in the early nineties, their voluminous, low-slung shorts ushered in the end of the “Tight Basketball Uniform Era.” Good thing, too. I mean, I enjoyed watching Larry Bird’s balls bounce up and down every time he stroked a three point shot, but generally speaking that shit had to stop. For single dude travelers to be taken seriously though, baggy clothes are never appropriate.
Let’s break this down. If you’ve taken the time to either get in shape or stay in shape, you need to show it off. This should be intuitive. We’ll get to the specifics later, but suffice it to say for now that dressing like your favorite rap star is going to hide all that hard work you’ve done in addition to make you look like a dumbass neanderthal basement dweller. Those dudes pull quality tail IN SPITE of how they dress because they are celebrity millionaires who can get away with wearing $1,000 pajamas to the club.*
Are you still fat? Do you really think big huge jackets and shirts are slimming? Bullshit. Not only are you carrying all those extra pounds, you’re sending a message through your attire. That message: “I am a slovenly mess of a man.” Pants hanging off your ass with cuffs that tear off underneath your shoes send a message that you don’t care about yourself. If you don’t care about yourself, why should she? Better than anything else, clothing that fits minimizes the appearance created by that extra batch of hot wings you’ve been eating weekly for the last ten years. It sends the message that you are confident in yourself, which does not come through in the layers and layers of sloppy clothing you think hides your extra pounds.
Don’t think you can overdo it either, too small is just as bad as too big. You know all those fat chicks you see who haven’t bought a new bra in ten years? Imagine one now. You know what I’m talking about – when you’re standing behind her in line you can totally see the entire outline of her bra through her too-thin sweater, because it is about two to four inches too small around to properly cradle her body. Instead it looks like it’s barely clinging to life, preparing to burst under the pressure at any moment. You know how her back fat slurps over the top of the bra and it kind of looks like two slop-nasty titties dangling off her shoulder blades? That nasty shit doesn’t work for dudes either.
Fit-wise, from head to toe, here’s a quick guide. If you need to wear a tie, your collar should button right up against that little soft spot in between your clavicles without stretching at all or leaving room for more than a finger or two. It should be snug without choking you. Your shirt sleeves should meet the body of the shirt exactly at the tip of your shoulder. The body of the shirt should be slim but not tight and definitely not tent-like (which is difficult to find off-the-rack in the States). The cuff of your shirt should end right at the wrist. If you’re wearing a jacket, err on the side of too much cuff showing than not enough. Too much cuff (maybe with some cuff links\) can look badass, but too little cuff screams “I’m wearing my daddy’s jacket.” Your pants should fit. If you have to wear a belt to avoid showing your drawers, they don’t fit. If you’re consistently picking a wedgie and the material bunches up around your junk, your pants are too tight. Lastly, the cuffs should break slightly (that is, the material should fold just a bit in front of your shin when you’re standing upright) and come to rest in a manner that your socks are rarely, if ever, showing. The bottom of your cuffs should never touch the ground until they are thrown with a Tarzan scream on the floor next to the bed of a hot Costa Rican girl with fake boobs.
You can forget all these specifics, though, if you follow this plan: find a decent tailor. Ask a well-dressed man where he has his clothes tailored if you don’t have one already. Address any issues right after you buy a piece of clothing. Your wardrobe will look a million times better and last much, much longer if you pay someone a nominal fee to make it fit on you.
While traveling, remember the most variable cost is someone’s time. If you go to a cheap single dude travel destination, go to a tailor and negotiate a made-to-order wardrobe. Nothing fits better than clothes made specifically for you. When I went to Thailand a couple of years ago I had the following made for me out of high quality fabric:
- 1 linen suit
- 11 shirts, both barrel and French cuff
- 4 additional pairs of pants
Total cost: $400. And this shit fits me today like a glove. This was one of the best investments I ever made. It’s probably worth buying a ticket there for $1200 bucks to go drink beer and play Connect 4 at the go-go bars, eat lots of delicious food, sit on the beach all day, get $6 massages every day and come back with a full new wardrobe. Where in the Western world can you party your ass off on the beach for a week and come back with a full new wardrobe for $2000?
Rule #2: Ditch the sportswear
Sportswear is appropriate for the gym, the running trail and the field, not the café, the club or the after party. Jerseys are appropriate when you are presently engaged in an athletic competition under contract with a professional sports team or at the sports stadium watching a game and at no time else. No one, anywhere in the world, gives a fuck that you are a huge Wes Welker fan and that you spent $300.00 to wear his jersey. And no, it is not any better to have a Christian Eriksen kit, totally before he signs with an EPL or Series A club, you fucking DAFF. If your clothing is going to be a conversation-starter, the conversation should have nothing to do with sports. Besides, you should be rethinking such purchases anyways – that sweet Michael Vick throwback jersey is worth hundreds of beers in Guatemala. Save your money, guys.
Rule #3: Suits are for business, not for slaying poon
If you’re on this site you’re probably not interested in the type of chick who is impressed with the fact that you’re wearing a suit in a social setting. But if you haven’t learned that lesson yet you should know all the reasons wearing a suit out makes you look like a douchebag.
Unless your business (concert promoter, head of security for the Sultan’s youngest son, night manager at TGI Fridays) requires it that night, wearing a suit sends the wrong message. You’re probably thinking it makes you look like a man of means, an important man – a man for whom business never ends. Ease back, Tony Montana. That’s not the message it sends at all. The dude in the suit trying to pick up chicks is the male equivalent of the chick in a Wonderbra. He’s trying to send an image that he’s something he’s not.
I don’t care what you tell me – if you wear a suit out to the bars, etc., you are trying to create an image of affluence. Wanna know how I know? Because a suit for any man, in any station of life, is the most expensive piece of clothing a man can buy. It’s like the opposite of the Macho Man T-shirt and cargo shorts discussed earlier. Wearing a suit is classic overcompensation. Whether you’ve got the money or not, you’re telling everyone that you’re in your Sunday best. For whatever it was worth historically, the modern two- or three-piece suit is acceptable business attire and nothing else. So when you wear a suit out to pick up chicks, the message you actually send is “I spent all my money on this suit, which I can also wear either to my job or my next court date, when I find out if the judge is going to let me into drug treatment.”
Besides, unless you’re rocking a made-to-measure Oxford or a bespoke Savile Row gem, you’re not fooling anyone. That suit that you think makes you special – we all know it’s not, especially those of us that have to wear the fuckers every day. Unless you’re used to wearing it, your suit is going to come off like costume jewelry, especially if it’s a rough-to-the-hand Donald Trump special you picked up on sale at Macy’s. Get your ass into the best menswear store you can find (hint: it’s not at the mall) and feel the good suits they have. They’re soft, drape well and ooze smoothosity (my made-up word). They could barely be categorized in the same group as the scratchy crap that is your typical mass-marketed suit available in the U.S. This is not snobbery – if you’re rocking a $400 suit you’re simply not important enough to be rocking a suit anywhere but at your particular cubicle, where it’s required.
To recap: When you’re wearing a suit out to meet girls and you don’t wear one every day, one of two possibilities exists: 1.) You blew your wad on a really, really nice piece of clothing that is completely inappropriate for the occasion for which you are wearing it, because you want to look special, or 2.) You bought a cheap-ass suit that is completely inappropriate for the occasion for which you are wearing it, because you want to look special. I’m not sure which one is worse.
If you’re wearing a suit to pick up chicks and you’re used to wearing it, you send the message that you can’t afford some sport coats or other “upscale” casual clothing. In other words, you suck at your job. Don’t try to convince yourself otherwise: If you’re wearing a suit at normal carousing hours and you didn’t just finish up the last day of a jury trial, you’re doing it wrong.
*I wish it known that I love love love rap music. It carries me through my day. Don’t take my advice here (or later in the article) to in any way suggest that my disapproval of the style of dress that is so common in the rap world is also indicative of anything other than an abiding love of the music. Peace to Biggie, 2Pac, Big L and Big Pun. Free Tru-Life. All that shit, man. Just pull up your god damn pants.