Marching Orders: Get up, go to your closet, and start making a pile. This is not the “try it on, one last time” pile. That pile always ends up back in the closet for another year. This is the proceed to Salvation Army and give it to someone who needs it more than you do.
Sympathy: Look, I get it. Ten years ago, those shoes were very cool. Or maybe they weren’t cool, but other people wore them. So they were “a thing.” Or maybe there’s a story attached to that tie or that jacket: you wore it when you graduated from college! It was a gift from someone you love. It retailed for $1,000 and you got it for $25! It doesn’t fit right, but you love the color.
No Sympathy: It doesn’t look good.
The List: I’ve owned every last thing listed below. I survived. You can, too.
1. Any sort of slip-on hybrid shoe. These shoes are essentially fancy Crocs, and I’m going to waste your time talking about Crocs, since now [clears throat] you only wear Crocs to the beach. And even that isn’t a good idea. As long as I’m at it, if the leather shoes you wear to work incorporate sporty-hybrid elements, get rid of them. 2. Any shirt where the seam falls below the beginning of the slope of your shoulders. As a man, your shoulders are your best feature, and they can compensate for anything else about you that you don’t love. But they can’t do anything for you when your shirt seams are midway down your arms.
3.T shirts with writing. You can donate both the Hulkamania Tshirt AND the irony to the Salvation Army.
4. Shoes with squared off toes. One word for you: platypus.
5. Running shoes / sneakers that you use for anything other than running / sneaking. The exceptions are Chuck Taylor / Converse sneakers because, if they are in decent shape, they are the tofu of the shoe world (they take on the flavor of anything you serve them with). Also, New Balance old- school sneakers because, unfortunately, it’s in (although becoming cliche) to wear them with blazers and the like.
6. White socks that you wear with anything other than the running shoes / sneakers while you are actually running / sneaking. Get some striped socks.
8. Khaki shorts. You will never wear khaki shorts with a tucked in polo shirt, running shoes, and white socks pulled up. Ever again. I call that look “Uncle Russ at the BBQ.”
9. Navy blue suit jackets which you try to pull off as a blazer. As long as I’m talking about blazers, I don’t care what size you are, you need to get fitted by a tailor. You should learn the NUMBER and the SIZE. For example, I’m a size 36 SHORT which is a Small. Only one in 500 jackets fits me. But I’m armed with that knowledge, and knowledge is half the battle.
10. Shiny Silk Ties. If your tie is shiny and silk, and probably picked up from a department store, then you should give it to your nephew for his Bar Mitzvah and replace it with something cotton (for summer) or wool (for winter).
11. Baggy Jeans. The 90’s called. They want their “The 90s called, they want their xyz joke” back.
13. Anything (especially shirts) that are a little too big. If it’s a little too big, it’s A LOT TOO BIG.
14. Snap-back baseball hats. Invest 10 more dollars for a fitted cap and only wear it when you’re at a little-league game.
15. Old-man caps except for one style: the 6 Paneled Ivy. Everyone looks good in one of those. (The worst old-man cap, by the way, is called a driving cap, and unless you’re an old-man, you shouldn’t wear it.)
Reassurance: You’re on your way to Salvation Army with two duffel bags worth of clothing you love but should never wear again. The only thing you have to wear now is underwear. So, for a week, walk around in your striped boxer-briefs with than zen-feeling that everything in life is impermanent, including not being in style.
That phase, for you, is over.
Get ready to get stylish.