The biggest hurdle on your way toward becoming a well-dressed man is not a lack of resources, or a lack of income, or a lack of knowledge. The biggest obstacle is, in all likelihood, laundry day. It’s on laundry day, when you’ve run out of decent options and your best is at the dry cleaner, in your hamper or, if circumstances are truly bleak, in a heap on the floor, that you will most be tempted to reach into the depths of your closet and revert back to your old ways, before you became the man you are today—one with a commitment to style. Which is why, much like an alcoholic needs to dump all his booze, and someone trying to lose weight can’t keep doughnuts in the house, you need to purge your closet of certain pieces that are holding your style back. Start here.
1. Slogan Tees
You may very well be kind of a big deal. You might take a hardline stance against messing with Texas. And maybe you are frequently in the company of Stupid. But even if you aren’t, the rest of the world will be more inclined to believe you—and notice your great sense of humor—if the punchline isn’t scrawled across your chest.
2. Novelty Ties
Remember that corny calculus teacher who once told your class that beer is never served at a math party because no one should drink and derive? He is the type of man who would wear a necktie in a rubber duckie print. It’s important to never forget about him.
3. Actually, Novelty Anything, Including Socks
It’s been scientifically proven that only .01% of the male population can successfully pull off wearing a fedora. It’s not that we don’t believe in you, but why play those odds?
5. Cargo Shorts
Like Tara Reid and “The Cha Cha Slide,” cargo shorts steamrolled their way into ubiquity in the early 2000s and still refuse to go quietly into the night. It’s time for us all to be the change we want to see in the world.
6. All Logo Everything
Certain slaves to fashion may fall prey to sweatshirts or tees emblazoned with designer logos. Leave it to them. If you follow the mantra of assembling a wardrobe full of timeless pieces, there’s not really room for overt branding.
7. Deep V-necks
Say what you will about the Amish, but no one’s ever had to stare at a mess of stringy chest hair emerging from beneath a deep V-neck T-shirt worn by an Amish man on a crowded subway in late August. And frankly, that is just as much a ringing endorsement for their wardrobe as it is for their entire way of life.
8. Oversized Belt Buckles
If you’re concerned about waste, perhaps consider melting your giant belt buckle down and using the remains to make 800 normal sized belt buckles. It’s a real win-win situation.
9. Ultra Distressed Denim
If you’re having trouble determining how much distressing is too much distressing for your jeans, ask yourself if the pair you’re holding onto could have ended up with those holes and that fade naturally. If the answer is a resounding “absolutely not” or “perhaps, if I were shipwrecked,” then you know what to do.
10. Square Toed Shoes
Here’s a quick lesson in footwear history. Brogue detailing was first introduced in 16th Century Ireland. Boat shoes were originally developed in Connecticut in the 1930s. And square toed shoes can trace their origins all the way back to the Gates of Hell. There’s really no two ways about this one: the only thing square toed shoes are good for is taking up room in your closet.