A friend recently asked me to help him update his wardrobe. Fashion is dumb, but the pursuit of style will serve you well. I wrote this for him, and am reposting it here, in the hope that one more man will toss his ill-fitting jeans.
Men’s style is about you wearing the clothes, not the clothes wearing you. A simple color palette and classic fits allow you to present yourself to the world, not distract it with pieces that are too big, too worn or too loud.
These are just rules, and for every rule, there are exceptions. Would I recommend a purple hoodie for everyone? No, but I’ve seen it work on an adult man, and I applaud him. Linsday Buckingham somehow pulled off a kimono! The best accessory you can have is being comfortable, and not wondering if you look like a tardbox in some trendy accessory (if you’re worrying about that, you do). The goal is to forget what you’re wearing, and the quickest route is simple pieces with a good fit. Blues and browns are hard to get wrong, and brown leather, flannel and corduroy won’t let you down.
throw a flannel/plaid on it. everybody does this now so it seems redundant but it’s tried and true: everybody’s getting done! Women like this because it makes men seem rugged, and what we really all want is someone to kill dinner for us. Same principle as beards. It pains me to admit this, but I seriously didn’t even KNOW I wanted someone to kill anything for me until I experienced the magic of beard burn. Most importantly, plaids look laid-back and cool, and that always wins. Make sure they’re well fitting.
shoes: no animal, vegetable or mineral should ever leave the house with running shoes if they’re not going for a run. The only exception to this rule extends to individuals who are already dads. It must be noted that they most certainly did not become dads by leaving the house in nikes and baggy Lees. Inconspicuous non-athletic sneakers are ok, ie Vans or something. Neon should be avoided unless you’re a 19 yo hip-hop star. I would encourage all men to venture into a non-sneaker of their choosing; the right one can be achieved by trying out styles at your friendly thrift store. I like a brown loafer, or perhaps a wingtip for the advanced. I’d stick to broken-in brown, black is too formal and you look like you stole them from a clueless dad from the 80s. Boots are masculine and suggest that you’re a cowboy or something, plus subliminally suggest “knocking boots” (maybe that’s just me), both good things.
T-shirts: T-shirts should be well-fitting and plain. You don’t want your shirt to say more than you do, so find a shirt slightly quieter than your own personality. I’ve seen people drown in their own design, and it’s sad. Conversely, I wanted to marry a guy in my freshman writing class who wore “World’s Best Grandma” shirts. Logos are gross. V-necks are a good way to go, deep-Vs for the gay or professionally sexy. A heather gray is classic, and make sure it’s not too long. Should fall about an inch below waist of pants, which leads us to:
Jeans: I cannot overstate the importance of your choice in denim. Style is about letting your clothes act as a backdrop for who you are, and nothing shrieks I’M EXTREMELY UNINTERESTED IN THE ACT OF LIVING like ratty jeans that cover your shoes. The only person in carpenter jeans I’ve ever even come close to wanting to jump on was a six-foot blonde glass blower from Vermont, because his carpenter-cut Lees (GUH!) said “fashion sucks, I’m a glassblower.” There is not another creature on the planet who can afford to commit that misstep. Your jeans should remain completely silent, and should have a tailored leg and a slim fit. All you ever need to know: Levis 501s. In medium-dark to dark wash. Nothing is a more effective panty melter than well-fitting jeans (with leather belt) a fitted t-shirt and some slip-ons or loafers.
Jewelry: Less is more. Too much and you probably also have tribal tatts and an ex-wife who you swapped for the swinging life style (ie drunk 18 year olds at alt-rock festivals).
A note on shorts: unless they’re denim cutoffs and you’re on a fixed Bianchi, I don’t want to see any skin below the knee. An exception is running shorts, which I personally will get into car accidents over. Cargo shorts are suitable for uncles and brotards whose most meaningful relationship is with their PS3 and bong, not people I want to date or whose opinion I would ever take seriously. On anything.
Sunglasses: Aviators or wayfarers, only, ever. Anyone with wire-rim sunglasses might as well also have DOUCHEBAG scrawled onto his forehead.
Accessory Overload is for Tweens: Nothing says “I DONT KNOW WHO I AM!” louder than someone drowning in trends. Unless you’re a Venezuelan-born psych-folk-singer with an expensive peyote habit and a bad actress girlfriend, forget trying more than one piece of jewelry/scarf/hat at a time (98% of dudes in fedoras are tools, the other 2% are balding). Belts are a good place to get in some detail if the rest of the outfit’s simple. Hand-tooled leather is classic.
For everything to avoid, see Gob from Arrested Development. For everything to embody, see Three Days of the Condor-era Robert Redford.
CHRIST I can’t believe I just wrote so much on fashion. I realize this makes me seem like one of those crazy beezies who secretly throws away her boyfriend’s favorite t-shirt because it’s old, which I would never do because that’s insane, and I actually don’t care that much.