I’m Pretty Sure I Found the Best Underwear for Men

It took a few decades, and involved some wardrobe malfunctions, but I finally found the perfect boxer brief.

by Peter Jakubowicz

For my Duluth Trading Company Buck Naked Nutcracker Performance Boxer Briefs, I would lay down my life.

I am grateful for this pair of underwear, the likes of which I have spent a lifetime seeking. My quest began with a wardrobe malfunction, years before Janet Jackson’s more famous Super Bowl mishap.

White cotton briefs, my mother’s choice, were my default underwear as a kid. Yes, the dreaded tighty whities. My dad wore boxers, of which I was envious.

Without a doubt, fathers should step up and choose their sons’ underwear, as they should step up to make circumcision decisions for their sons, who are too young to speak for themselves.

Mothers don’t know how much wearing tighty whities (the skimpy Speedo briefs of men’s underwear) sucks, any more than they know the feel of the penis that boys have inherited from their dads. I still resent my mom for sticking me in tighty whities and my dad for not backing me up when I asked for boxers. I’m OK about being circumcised. But I hated having to waste valuable minutes of my childhood adjusting myself in my tighty whities while trying to look as if I was doing something else.

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Now, about my wardrobe malfunction. One day, my grandmother was visiting. She washed, dried, and folded our clothes. As she was putting away my tighty whities, she saw the flies, which she took to be rips in the fabric. She did not want me to go around with holes in my underwater — so, she sewed them shut.

My grandmother was OK, although she sometimes did things like mistake the flies in my briefs for holes in the fabric, and then render them useless by sewing the flies.

I had not known the phrase at the time, but I have later referred to the event as my wardrobe malfunction. I only realized my grandmother had done this the first time I tried to piss, while wearing my newly renovated shorts, in a public bathroom. And it took a while to work out what had happened. It was, as my kids like to say, awkward.

It was then that I decided I could do better than tighty whities. I stepped up and told my mother I was switching to boxers, and no, we were not undoing Grandma’s handiwork. Boxer briefs were not yet widely available. So, I wanted boxers like the ones my dad wore.

Oddly enough, my mother took to buying me boxers. But she never bought plain, monochrome ones. I wanted blue boxers. Instead, I got ones with weird cartoonish-designs, bright pinks and oranges, and mottos that did not apply to me. I did not question her motives. I was too happy not to have to have to adjust my constricted self anymore. Or to have her quizzing me about where that stain came from. Tighty whities don’t stay white; the name is ill chosen. Dingy Dickies is more like it.

Later, when I was in college, for Valentine’s Day, Mom got me Minnie Mouse boxers, covered with the world’s second-most-famous cartoon mouse puckering up, pink hearts, and ”Be My Valentine” emblazoned all over them. My male friends were WTH-ish about them. But girls thought they were cool. I kind of liked them.

I used to walk around in them in an apartment I shared with two grad students in Somerville, Massachusetts. Once, one of my roommates told me his mother was visiting. I said that was cool. And then he stared tellingly at my shorts. I got it: meet roommate’s mom — but not in my freaky boxers. The thing about boxers was they were still obviously underwear, not something you wear when meeting someone’s mother. Maybe I grew up a little at that moment.

When I first came across hybrid underwear (boxer briefs), I was smitten.

There are lots of boxer briefs out there, many of which are too white and tight: tighty whities by another name. I hate being constricted by underwear, and yet I would not go without them. I’ve met guys who say they don’t wear any. But then I always remember my grandmother, who really did tell me to make sure my underwear wasn’t holey in case I was hit by a car. What would the EMTs say, right?

Plus, what if you had an accident in the bathroom? It would be weird holding your hands over the wet marks on the front of your pants, and worse yet if you’d tried to clean it up with paper towels and smelly office bathroom soap. We’ve all been there, I expect. So, sans underwear was not a doable fashion choice for me.

Duluth Trading Company makes the best boxer briefs ever. I have no affiliation with Duluth Trading Company, but…these boxer briefs.

They are the most comfortable ones I’ve tried. They’re roomy but not baggy — made for someone like me, who is not comfortable on the high diving board wearing leave-nothing-to-the-imagination Speedos. But who gives a shit about looking OK in his underwear. The fabric is soft enough that they don’t itch or chafe. They are so comfortable you barely notice them. And they come in all kinds of cool colors and designs. I have never worn out a pair, either.

Best of all are the flies. The flies either have buttons or are incorporated into the fabric in such a way that they don’t look like flies. In either case, my grandmother would never have mistaken them for holes and sewn them up on the sly.

My favorites are one of the special Christmas ones I own and wear with pride at least once a week. They are bright red, covered with Christmas nutcracker guys and swords crossed with sheaths. I love them, and I think of my mother each time I put them on.

Peter Jakubowicz lives in Portland, Oregon, with his son and daughter. He is a writer, plays hockey, and is a little picky about his underwear.