The Clothes I Wore In High School Explain Why I Was The Only One In My Pants All Those Years

I’m home in Maine for the Fourth of July and my mom told me we have to take a bunch of my old clothes to goodwill because she wants to turn my bedroom into a study. I tried to explain that there were simpler ways to tell me not to come home anymore, but mom seemed hell-bent on not hurting my feelings. So I started going through my old clothes, and it was a jarring experience. Obviously, that which is “fashionable” changes all the time. I’d have to consult with the Failing Upwards guys but my general sense is that slim-fitting clothes have been the trend for men of late. At least that’s what I’ve seen in Chelsea. Slim-fitting pants with holes in the pockets so your pal can grab shaft for a few strokes before the crosswalk light changes.

My style changed a lot from when I was about 13 until I got to college. That’s the important period of study because I started choosing my own clothes around 13. Up to that point, it was sweatpants and athletic shorts every day. Then the boners started happening out of nowhere and I needed raw denim, a metal zipper, compression shorts, and ace bandage wraps to tamp them down until I could waddle into the handicapped bathroom at school. Poor janitor had to nuke that sink with drain-o twice a day.

What I learned today was that the styles I thought were cool 10-15 years ago look preposterous on me now. More importantly, clothes that I thought fit me just didn’t. I’m actually about 30 pounds heavier now than I was at 18, and these clothes are legitimately fucking HUGE. You can’t say I was going for a ghetto fabulous look either because I stopped wearing Fubu in 6th grade when I realized “For us, by us” didn’t include me.

Without further ado, here’s a little fashion show of my old styles! These are REAL outfits that I used to wear. I would suggest that you guys do a similar exercise next time you’re home.

1. Holla if you Hollister

Hollister cargo shorts with a rugby. Put together, this outfit weighs 15 pounds. Cargo shorts get a bad rep but man are they practical. The camping backpack of clothing. A shipping container of shorts. These bad boys had more pockets than a fleshlight factory. Meanwhile, the shirt let people know that you were ready for ANYTHING. God forbid a rugby match broke out, I was ready to learn the rules and play.

I checked the tag on those shorts and they’re a size 36. I’m a 34 now, sometimes a 33. In other words, I wore shorts that were 2-3 waist sizes higher back when I was 30 pounds lighter, and that is not how science works. These things are fucking ENORMOUS! Have you ever seen shorts that you had to CUFF?! I have to roll these at the bottom just to let my shins breathe. God forbid I forgot a belt with these parachutes, I’d have my hands in my pockets all day like those boys in Chelsea.

2. Madrascal 

“Excuse me, sir, but have you seen my croquet mallet? My polo pony appears to have run off with it, along with my wife! Haha that thieving bitch, let’s hope she swims home to Venezuela. Lord knows she’ll float on her back with all that rubber she has in her chest!”

Just your typical Hamptons cocktail party banter, probably. What did I know? I’d never even heard of the Hamptons at that point. I bought this thing at a Brooks Brothers outlet in Freeport for like $60. Wore it to a prom at some neighboring school as a gag. My date was furious because my quilt coat clashed with whatever stupid dress she wore. Not sure how that’s possible because this coat paints with all the colors of the wind, so there should be something in there that WORKS with your fucking DRESS, you MORON. If you wanted some stiff in a rented black tux, you shouldn’t have asked the bulldozer.

3. A pinnie for your thoughts?

Let’s start with the pants. The cut? Boot. Might even be double boot. I swear to God, when I bought those khakis I thought they were slim on me. Really did. My thighs felt like they were stuffed in condoms. But the manager said “they’ll stretch.” Fairly sure the only place they stretched was at the ankle because you could smuggle a family of six over the border in the legs alone. Not an inch of fabric is touching my legs. Not an inch!

Luckily, the lax pinnie steals the attention away from my lower body. Champ camp bro, ever heard of it? Our Maine team went down there and… finished dead last. Those Maryland/Pennsylvania/Long Island/Virginia kids really know how to play. Did I mention it’s reversible though? White on the inside, just like a daffodil stem or a mounds bar.

4. Ron Mexico

I reffed youth soccer games for an entire summer to save up for this Mike Vick authentic jersey. He was the most electrifying athlete in the NFL at that time. I revered him so much that when the whole dog thing came out, I couldn’t understand the fuss. And I love dogs! It’s not like he was fighting yellow labs or St. Bernards or something with a fluffy face and a wet nose. He was fighting pitbulls, and pitbulls WANT to fight. You might even argue that keeping pitbulls out of the ring is cruel.

Check out this badass pooch I’ve got though. I’m ready to scramble for 60 and she’s ready to rip throats. But in reality, I wore this thing to AP Calculus while she ate her dinner so fast that she puked it up, and then ate the puke, which is tough to watch. Those were the days.

PS- hey Liz Gonzalez, not to sound racist but yellow labs >>>> chocolate labs. Something about the dark eyes and nose standing out against the golden fur. Striking. It’s the same reason blonde women wear dark mascara, something I learned in Cosmopolitan Teen.