Cultural Caviar

An Idiot’s Guide to Getting Dressed

December 11, 2015

Multiple Pages
An Idiot’s Guide to Getting Dressed

A millennial walked into my office this week looking like a simpleton with a court date. He had a cheap suit on with square-toed shoes and his hair lay flat on his forehead like Jim Carrey in Dumb and Dumber. His shirt came straight out of the dirty laundry and the collar on it was so crumpled it sat over his blazer like a pile of used condoms. When I began to list the dozens of fashion crimes this young man had just committed he stared at me like a Papua New Guinean being shown how to open a tin. I’m beginning to think young men have been dressing wrong for so long, they no longer know what’s right. I came of age in the ’80s when mods set the template for how to dress, but today all they have is Reservoir Dogs and Men in Black. Those guys don’t even use pocket squares.

If you are an adult male working in a professional environment and you want to be taken seriously, you need to wear a suit. That means you also need a briefcase, a bunch of ties, some comfortable shirts, a new haircut, and three pairs of shoes. I can afford the finest tailors on Savile Row, but I am Scottish and we are so cheap, Jews think we’re being sarcastic.

The first thing that separates the men from the boys is the top button. Wearing a tie with your top button undone tells everyone you work with that you don’t know how to buy a shirt. I realize it can be stifling to button up that tight and this is usually because fat pigs have skewed the shirt market so wide that everything in your size of neck is a gigantic sheet. The solution to this is to either buy a shirt based on how the top button feels around your neck and then have a tailor take in the rest of the shirt or have a shirt custom-made. For all minor adjustments like taking in shirts, tapering pants, and hemming jeans, I use the Cambodian lady at the Laundromat, but for creating something from scratch you need a pro. Local tailors are way too expensive, so those of us in the cheap community use nomads. These are usually third-world types who travel from city to city renting hotel rooms that us penny-pinchers invade a few times a year. Nita Fashions is one such company. They take your measurements, show you swatches, and then fulfill your order back in Hong Kong where labor costs nothing. You can get a custom dress shirt from them for as little as $50 and it fits so perfectly, you feel like you’re wearing pajamas. Dry cleaners take about three days to turn around an order so you’re going to need at least five shirts to start with. I recommend white because anything else is hard to match and patterns make you look weak. If you can’t afford to change your shirt every day, just wash the armpits in the sink and then iron it dry. This trick also comes in handy on business trips where dry cleaners are not an option.

“Do not buy a suit at Men’s Wearhouse. The suits from there look like they’re from Men’s Wearhouse.”

If you’re going to wear a shirt without a tie, you don’t need to worry about the top button. In New York, Century 21 has high-quality dress shirts that have been marked down, but you can also get great cheap stuff at Uniqlo and H&M. Ted Baker and J Crew are about double the price, but if you keep your eye out for sales it’s easy to get shirts there for $50. I like a button-down collar so it never pokes over my lapel, but that is frowned upon in formal settings (most who have a problem with this will stop mentioning it after a quiet “Fuck off”).

Do not buy a suit at Men’s Wearhouse. The suits from there look like they’re from Men’s Wearhouse. They’re for security guards and weddings where you hate the bride. Real suits should have pants that you’d wear alone as pants. My tailor will make them for under $1,000, but I was shocked to see the same quality of suit at J Crew for $600. Go black or very dark and you only need one. That’s the beauty of being a man. Once you have your five shirts, your black suit, and some brogues, you’re done. All you need to not look the same every day is a change of tie.

Your pants should fit close to the leg and should end abruptly at the shoe with maybe one wrinkle. Young men today should have a suit that is almost too small for them—not quite Pee-wee Herman but close. When your jacket sleeve goes past your wrist, you look like you’re shrinking. You want your white cuffs to be jutting out from a suit even when your hands are at your sides. 

A three-piece suit is a great look because it keeps your shirt from bunching out, but it’s only suitable for the winter months. Wearing a sweater under your suit is almost never acceptable. Lawyers who commute from the suburbs always do this and it makes you look like a golf accountant. It’s also way too hot. Wearing a cardigan under a suit is a bad move because you look like Mr. Rogers when you take your blazer off and V-neck sweaters with a blazer are for Ned Flanders.

Which bring us to what makes the man: shoes. In the action flick Kingsman, the password for the Bond-type character is “Oxfords not brogues.” I don’t know why. Oxfords are boring. Brogues make you look intellectual and they age beautifully. A good pair can set you back $400 but they last forever and you can keep repairing the soles. Another fantastic shoe is the tasseled loafer Loake makes, especially the Brighton with the welted rubber sole. It’s over $200 but Doc Martens does a rip-off called the Adrian that’s much cheaper.

If you’re really on a budget, you can’t go wrong with the Clarks desert boot. Brown is the classic color, but you can’t wear that with a black suit so you’re going to have to settle for black. I’d go for leather not suede because it fares better in the rain. Speaking of getting wet, get wet. You can wear a trench coat and maybe even a fedora but no man should ever be seen with an umbrella under any circumstances. Being afraid of water is about as unmanly as it gets.

You should carry your computer and documents in a briefcase, not a backpack. It’s infuriating seeing grown men wear suits with some stupid x-treme sports backpack that has a waterproof jack for headphones and a utilitarian clip holding hand sanitizer. That’s for homework, not mortgage applications. Your briefcase should be hard and leather, but if you want to go more casual, get a Filson. You should never have anything that goes over your shoulder, and only I.T. guys carry nylon bags. The same goes for flying. Your suitcase weighs only 20 pounds, so carry it like a man.

Gays have heavily influenced the price of men’s clothing and it’s hard to find a tie in New York under $100. If you go to, however, every tie there is around $20. Their socks are also cheap, running under $10. I highly recommend fagging out when it comes to socks. This is your place to shine. Pink, electric blue, and even ones with a guy mowing his lawn show that you’re funny and capable at the same time. Mixing your tie with your socks is another place to get gay but make sure you never combine red and pink. They look terrible together. There was a rumor that “blue and green should never be seen” but it’s been disproven.

Pocket squares are also available at the Tie Bar and I get mine from Michelsons, but the bill is mounting here and I understand cheapskates wanting to tap out around now. Here’s a tip I still use regularly: You can make a perfectly good white pocket square using toilet paper. The friction grips your pocket nicely and if you ensure only a slim line is showing, nobody will notice. Do not use paper towels for this. I tried it once and the intense ridicule I suffered after the textured pattern gave me away was tantamount to being raped.

It’s good to procure a wide variety of ties because they are what differentiates you from day to day. Slender beats wide but never underestimate the merits of a flat, black tie. It’s perfect for every occasion. Bow ties take some balls and YouTube is very good at showing you how to tie them but excessive bow-tie wearing makes you look like an old-money dork with Asperger’s.

As a final touch, I love a good pair of suspenders. Northerners seem to think combining them with a belt is redundant, but Southerners and tradesmen do it all the time. When you do that with a suit, it separates you from the bourgeois ponces at The New York Times.

You’re almost finished, but we need to make sure your head isn’t hard to look at. My colleague with the floppy hair was only a comb away from looking decent. I recommend the most old-fashioned barber available. My barber charges $25 for a trim, but if you go to a barber school, the most they’ll charge you is $5. “Short back and sides” should cut it and if you need to tame a wild ’fro, nothing beats Razac. It’s used to tame black women’s hair and as we’ve learned from de Blasio, if you can handle black women, you can handle anything. As far as facial hair goes, I don’t expect anyone to take me seriously on that front so I’ll let you decide. I have no chin and was forced to grow a pile of it but if you’ve got a chin, I can’t understand why you wouldn’t want a mustache. Jon Taffer’s top lip is all but screaming out for one.

That’s all you have to do. The briefcase can wait. A haircut is $5. Desert boots are $100. A J Crew suit is $600. Socks and a tie are $30 and a toilet-paper pocket square is free. That’s $735 to go from mongoloid to millionaire. All we have to do now is convince millennials it’s worth it.

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