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.

Filson Original Briefc... Check Amazon for Pricing. 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.

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”).

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