There aren’t a lot of things in life I enjoy more than when someone stares my clothes down. It’s been documented and commented on before. I dress somewhere between a wannabe Connecticut trust fund kid and a retiree, and I absolutely love it. The looks I get at the bar vary from “Wow, look at this douchebag, let’s try and fight him” to “Wow, I hate this guy and he hasn’t said a word yet, but I sneaky want his outfit.”
At the end of the day, the thing with getting mocked over what you’re wearing is that if you like it, then fuck everyone else. You know that phrase, “Any press is good press?” Well, that pertains to attention as well. Any attention you get is a good thing. As long as it doesn’t involve you getting too drunk, fighting with someone, or throwing up somewhere you shouldn’t. Embrace the hate. Let it flow through you.
I remember last Fourth of July when I was at a hole-in-the-wall bar in a Michigan beach town. My crew had been drinking all day, and I drunkenly opted for a pair of loafers, some khakis, and a golf polo/sports jacket pairing. In retrospect, it probably wasn’t the right crowd for this kind of ensemble. Didn’t care then and I don’t care now. I was drinking Bud Lights just like everyone else. Not like I rolled into this shitty bar and ordered a gin martini.
I got some dirty-ass looks from more than one townie, but I ended the night hooking up with some random who only noticed me because the group of guys she had showed up with were making fun of me from across the way. Someone gives you a condescending, “Nice outfit, bro”? Give them a good old fashioned politician wave, smile and then say, “Thanks for your support” and walk away. Kill ‘em with kindness.
You want to wear bootcut jeans and a hoodie to your friends party? Fine, I don’t give a shit. It’s not the most up to date stuff out there, but do you. I’ll wear some Orvis Tartan plaids, a sick LL Bean sweater and we’ll shoot the shit. I can talk anyone’s ear off if you give me an in. If your in happens to be, “You dress like a tool,” there’s a chance I’ll be able to turn it around once I open my mouth and make you realize there’s more to me than my carefully crafted, nautically themed wardrobe. And if you still don’t like me after our conversation, fine, judge the shit out of me. I’m an acquired taste, not everyone likes me.
I recently bought a pair of joggers on the advice of some friends, and although I loved the look on them, I simply can’t pull them off. Joggers are for the sneaker crowd. Aside from the ASICS I wear to the gym, I don’t currently own a pair of sneakers. I feel like I need a pair of Jordan’s or something to wear them, and I can’t justify buying a pair when I’d rather spend that money on a pair of nice Weejun’s from Bass (Weejun’s are penny loafers, btw).
The joggers I bought just looked ridiculous when I paired them with anything in my closet (mostly pastel button downs and a few pocket t-shirts). And that’s okay. Everyones got their own style. I’m not going to sit here and tell you that cargo shorts are a good look, because they aren’t. If you’re going to wear shorts, clean it up with some freshly ironed khakis. No more than four total pockets — you’re an adult. You can’t be walking around looking like that kid at your middle school who sold gum and kept all of his earnings in the cargo pockets.
Dress how you want to and let them stare. There’s probably someone in that party or bar that digs it. .