The Boston Bachelor

BY THEBOSTONBACHELOR.COM / July 8th, 2008

I’m not here to sell you any products. I’m not here to get you to click on referral links (see my Top 10 Underrated Movies list below for that). And I’m not here to blow sunshine and moonbeams up your ass.

But if you want the raw, uncensored truth on mens’ fashion, then keep reading. I’m no fashion guru, and I could give two shits what sarcastic gay guys on E! say about the outfits people wore at last year’s Oscars. But what I do know from firsthand experience is the power of insecurity, peer pressure, and marketing, and how it relates to the world of fashion. So buckle up, ‘cause it’s time to cut the bullshit and get real.

Let’s start by examining the 7 types of guys out there from a fashion perspective:

Mr. Clueless:

Just wears whatever clothes he bought back during tech school or that he got for free from his IT job. Can’t understand why anyone would spend more than $30 on a pair of shoes.

Mr. Safe:

Is happy as long as he doesn’t stand out. The worst thing that could happen is for someone to notice his clothing and give a negative reaction, even if the overall number of positive reactions he gets greatly outweighs the number of negative reactions. Usually dresses like a 50 year old man, regardless of actual age.

Mr. Trendy-Safe:

Believes that looking cool is the epitome of mens’ fashion. Religiously follows the advice in soul-numbing advertisement brochures, I mean, magazines such as Maxim and FHM and websites such as AskMen.com.

Mr. Super-Trendy:

Has to be on top of the latest fashion trends. Spends half his salary on clothing that’ll be out of style in a few months. Frequently visits sites like The Sartorialist and leaves catty, condescending remarks.

Mr. Clone:

Wears whatever makes him fit in to his peer group. Has an urgent need to belong. Examples: Hipsters, preppies, punks, Goths, skateboarders, hippies, jocks, hardcore rockers, frat guys, hip-hop heads, yuppies, etc. Isn’t it amazing how everyone in these groups is unique in the exact same way?

Mr. Spite:

Dresses like a bum in order to stick it to either a) “the man,” b) Dubya, or c) our capitalist society. Deep down is insecure about his looks and angry at the world.

The Individual:

The advertiser’s public enemy number one. Doesn’t care what others think of his fashion, but not in a reactionary or spiteful way (see above). Has enough intelligence to understand what looks good on his unique body/bone structure/physique. Knows the fundamentals of fashion, but isn’t a slave to them. May be a trend setter without even knowing it (or caring if he is). Enjoys good fashion for the creativity and expression, the same way one can enjoy good art or music. Has confidence whether he’s dressed like a complete scrub or to the nines. This is who you want to be, and by following these 8 simple rules, anyone can get there.

Rule #1: When buying clothes, the most important criteria is the fit.

Learn it and remember it. Tattoo it on your face if necessary. Know your measurements, and from now on only buy clothes that match them. A great-fitting $30 dress shirt will always look better than the $200 dress shirt that’s an inch too big on the shoulders and chest. The same way most women believe that they’re a size smaller than they really are, most men believe that they’re a size bigger than they really are. Ever know a guy who refuses to wear a size Small shirt even though it would be the perfect fit? If you ask me, it all comes down to made-up insecurities. I think deep down guys like that believe that a size Small equates to a weak body or a small penis in the eyes of others. If you have a better theory, I’m waiting to hear it.

Rule #2: Know how colors work.

Find which colors complement each other and which don’t. For starters, match the belt, socks, shoes, and watch. When it comes to tops and bottoms, kill the blue on blue and white on white routines. And unless your name is Bob Dylan, stay away from Blonde on Blonde (buh dum chsss!) I-say! I-say! Know these first 2 rules, and from a purely superficial standpoint you’re already doing better than 90% of the male population out there.

Rule #3: Accessories can hurt you or help you.

Glasses, watches, belts, piercings, hell even sideburns. Every little thing matters. If it’s not helping you, it’s hurting you.

Rule #4: Just because it’s trendy doesn’t mean it looks good on you.

Skinny jeans seem to be in-vogue for both men and women at this time. Does that mean most men and women look good in them? Fuck no. Again, know your body and physique. And if you still don’t believe me, then let me remind me you of flannel shirts, genie pants, neon shorts, jeans with the boxers sewn into them, etc.

Rule #5: Know the law of diminishing returns.

I’m not one of those people that says spending any more than the minimum on clothes is a waste when you actual calculate the cost it takes to manufacture and ship the product. Sometimes it is worth it to spend a premium to get the quality and look you want. But you do hit a certain point when you have to ask yourself whether those $500 Japanese selvage denim jeans really worth the asking price. At this point you’re paying for the billboard ad and downtown Tokyo retail rent space, not the actual jeans themselves. And if you think that’s bad, don’t get me started on the law of diminishing returns as it applies to womens’ fashion.

Rule #6: Be open to advice and criticism.

Many guys get real uptight and defensive when given suggestions on fashion or grooming. You don’t have to take the advice, but it never hurts to lend an open ear. Don’t let your ego fuck up your progress.

Rule #7: Step outside your comfort zone.

There is nothing that will get you that “asexual boring nice guy” stamp on your forehead than dressing like a conservative office drone. Again, most people (and not just men) are terrified of how their friends, coworkers, family, and even random strangers will perceive a change in fashion. The fact is, no one really cares. And if they do, then it’s because they’re jealous of your newfound confidence and insecure about their own inability to take action. Hey, at least you’ll know who your true friends are.

And finally… the most important rule of all…

Rule #8: You are not your clothes.

Whether you loved the film or hated the Film Club (personally I thought it was uneven), there’s one line from that film everyone should heed: You are not your fucking khakis. And I’ll take this a step further…

You are not your fucking mesh trucker cap.
You are not your fucking Abercrombie shorts.
You are not your fucking black motorcycle jacket.
You are not your fucking Converse sneakers.
You are not your fucking Sean John polo.
You are not your fucking Adidas track suit.
You are not your fucking Affliction t-shirt.
You are not your fucking black hoodie.
You are not your fucking True Religion jeans.
You are not your fucking Birkenstock sandals.
You are not your fucking Hugo Boss suit.
You are not your fucking Ray Ban aviator sunglasses.
You are not your fucking Dickies.

Remember back during high school when cliques were based on fashion and outward appearance? You had the preppies, the Goths, the skateboarders, the hip-hop heads, the stoners, the hippies, etc. We were all conditioned to believe that appearance = identity. I remember as a kid thinking how if I only I had the Jnco jeans and the Airwalks, I would fit in. We’ve all experienced this type of insecurity at some point in our lives; it’s an unfortunate side effect of growing up in the modern world.

Sadly most adults today still carry around this crippling notion that clothes and fashion make one’s identity. If I put on a fisherman’s vest, does that necessarily mean that I know how to fish? If I buy an oversized Ecko hoodie, does that suddenly give me mad freestylin’ ability?

Look, there’s nothing wrong with, for example, wearing the shirt of an obscure band you like. But you have to ask yourself this: Am I wearing this shirt in the secret hope that some hot hipster chick on the street will recognize my “indie cred,” or am I wearing this shirt because I honestly like it, regardless if anyone’s around to see it or not. If everyone else in the world suddenly went blind, would I still buy it and wear it?

So there you have it. You are not your fucking clothes. You are also not your fucking job, your fucking bank statement, or the fucking car you drive. You are you.

I’ll leave the final words to dating guru Owen Cook, on that warm, fuzzy, temporary self-esteem boost most of us get from a nice new haircut, shirt, or pair of shoes.

“Has it ever occurred to you that maybe you should feel that way all the time?”

I couldn’t have fucking said it better myself.

-The Boston Bachelor