These Are My Regrets, Volume Four: Hats

I used to buy (and lose) the fake Mets hats in high school in between saving money for new “real” ones that I would also constantly lose. I have no idea why I took them off so often—and this was before I started drinking—so lord knows how I lost anything at all. At least twice I remember looking at a hat of mine sitting on an orange F train pulling out of the station for the next stop.

Hats have always suited me. My guess is they let me hide, which is what I like to do with clothes: jackets, boots, sweatshirts. That’s why the summer sucks for me, clothing-wise. There's nowhere to hide! Shorts are for children. What am I supposed to wear, a graphic tee? I’m too haired-up for tank-tops. I’m regrettably that dude who starts wearing a skully weeks before it’s appropriate. Ski caps have got to be my favorite headgear. Believe it not, I’ve never even been skiing.

I started wearing “trucker” hats in 2000 with my brother’s old little league hat. I’d wear them with these cheap Russian polyester shirts (five of which I was could buy for 20 buck), Indian slacks, and Bata rubber shoes made with what looked like old tires. That’s about the most outlying style I’ve worn in my life, and that was pre-trucker hat-popularity. Before they were popular in New York, at least, I don’t care about like, Portland or whatever. There was also those two years I wore a trilby hat.

Recently, I got off the bus early to walk down Hillside Avenue in Queens to see how the strip had changed. It hadn't, really. Lots of Bangladeshi Halal meat spots, Guyanese food, Crown Fried Chicken, and 99 cent stores with the outdoor displays, including the infamous runner rug spools. I’ve found some great hat finds in stores like these, including the now-lost “Cup Crazy” hats, which I snapped up five of and promptly lost a few years back.

In two bins I found about a dozen each of these beauties. Super simple hats with something “wholesome’ about them that I can’t quite put my finger on. They look like the type of hats that the friends of early ‘90s sitcoms “younger brothers” would wear. They also reminded me of the white tomboy girl named Sam from the PBS children’s show Wishbone. I walked inside to pay the 79 cents a piece for them and jumped on the bus. When I finally tried them on I realized I’d once again been done in by my too small, overly rectangular head.

This has been a problem for me since I started regularly wearing baseball caps in middle school. Fitted hats look terrible on me also. There’s too much room on the sides and when I pull them too far down, we’re gonna have an ear-pop-out situation. Pull your hat down too low and the top half of your ears start sticking out. Unacceptable. These hats presented a different problem entirely, the top bulge that makes them look ridiculous. They look half-decent backwards, but I’m not really going to do that now, am I? $1.58 down the drain, in a recession no less. The one saving grace is the label inside.

I found this after recently eating at “House of Vegetarian” on Mott street in Chinatown. I love that place. I recommend you go there at least once and try the sweet and sour chicken made with white yams; it’s pretty nutty. Anyways, this hat was right next door in one of those “I Love NY” shirt-swimming diver toy-baby turtles-hats stores, you know what I’m talking about. I tried it on repeatedly, looking at myself in the little mirror. I thought, “Maybe I could wear this one time to a thing where I don’t care about my appearance.” It didn’t fit ideally, but for whatever reason I thought it was passable at the time and I bargained it down to seven dollars from an outrageous 15. Imagine? Actually, I didn’t bargain so much as say “seven” twice, once after the woman said “15,” and a second time after she said “ten.” I also hadn’t seen this guy at any other similar stores in my recent jaunts through that part of town, which was important.

Once again, we have a very prominent top bulge combined with a very prominent sweatband. The hat is more than half the size of my head. Another failure. In other news, I was recently considering buying one of those Hindu god shirts I’ve seen white people wearing around town. They’re made in India and I like the rough fabric, but I figure I’ll just go to India and buy one for a nickel.

I had a period a few years back where I was buying and wearing eccentric hats left and right. Thankfully, this period is over, not completely unrelated to having lost all those hats. Well, all but one. This tacky piece of garbage I bought on tour somewhere in the Midwest for, I think, three dollars. That’s eight packs of gum (40 pieces) or two of these miracle Virgin Mary candles downstairs.

What am I supposed to do with this? Where is the appropriate place to wear this? My best bet is to wait for a friend to have a (hopefully big headed) baby and try to pass this off as a gift.

I thought this would be a nice formal piece to wear with my blue jumpsuit if we ever had to play some rich kid’s 16th birthday party or a quinceañera.

I obviously planned to pull of the bow at some point, because I’m not crazy.

I don’t regret this one at all. I just wanted to post this photo.

If anybody wants to purchase one of these hats, please don’t hesitate to contact me.

Dapwell actually doesn't regret his hats. He's on Twitter — @dapwell