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Tailor & Barber
Tailor & Barber

A men's lifestyle blog focusing on style, fashion, and grooming.

What Underwear Do I Wear

What Underwear Do I Wear?

Posted on February 8, 2021February 7, 2021 By Drew

Over the past few months (and for probably even longer), I’ve been trying to figure out what the best underwear for me is. My trials have run the gamut. I tried boxers shorts, which always seem to get too bunchy making them especially uncomfortable in the hot months. Boxer briefs are alway too long in my opinion. If I wanted to wear biker shorts, I would have already hopped on that trend (note: I haven’t). Briefs (tighty-whiteys) are actually quite comfortable and supportive. I prefer them not to be white. But, they are also a tough sell for a lot of guys, and I think they truly look good on pretty fit people, which is not most of us (myself included) after quarantine. So where does that leave me? With the best option of course, trunks.

For me trunks are the solution to all my underwear problems. They are supportive. I, for one, do not prefer the feeling of dangling in the wind or sweat-induced sticking problems. I want something that cups and supports, like a bra for the boys. But I also want to be comfortable without any squeezing or chaffing. And, call me superficial, but I want to look good too. I think, being in any position of only wearing your underwear is already an insecure experience, having a little confidence knowing you look good in your trunks is definitely a plus. I’ve tried out four different brands of trunks, and I have some thoughts on all of them. While one is not necessarily better than the others, I do have my favorite.

Kronis ($10)

What Underwear Do I Wear
Kronis Trunks

These Italian-designed trunks are a great value. For $10, they’re comfortable, low rise, and come in a variety of colors. Be forewarned, though, they are a bit shorter and snugger than some of the otters on this list, and you may want to size up.

Sunspel ($38)

Sunspel Trunks

These were, without a doubt, the highest quality trunks I tried. The cotton is soft. They stay put. The elastic never loosens. Unfortunately, there are two other problems. The first is functional. They have no fly. I understand the concept behind this design, namely more support. However, I don’t think I will ever be able to commit to unbuttoning my pants every time I have to use the facilities. I know it sounds silly, but I enjoy the simplicity and quickness of using a fly. The second issue with these trunks is, obviously, the price. To me, they are a bit steep for a pair of underwear. I won’t say they’re not worth it, because Sunspel trunks really are quite comfortable, but $38 is a hefty price tag for me.

Boggi ($29)

What Underwear Do I Wear
Boggi Trunks

Another Italian brand, these trunks are made up of mostly cotton (with a little elastane) and are very comfortable. If you’re into a minimalist underwear style, these should be your pick. They’re available in black, navy, gray, and white. And that’s it. One issue of which to be aware, is that they are shipped from Italy. Unfortunately, Boggi doesn’t have any American stores (yet). Returns have to be sent back to Italy too, and that can be a little tricky if you aren’t satisfied.

Mack Weldon ($22)

Mack Weldon Trunks

These are my pick! They’re made with a mix of cotton and modal, but don’t feel like some modal underwear. They feel like cotton. They’re supportive and come in a variety of colors and patterns, so you can be a bit more playful. Ordering is simple, and your first pair is free if you don’t like them. So you can definitely give them a shot without worry.

Most guys don’t put too much thought into their underwear. They grab a few pairs of boxers from a big clothing retailer or stock up on multipacks from their local big box store. But if you take a few extra minutes and buy from a brand that specializes in underwear, you will experience much more comfort below the belt and maybe feel a bit more confident when down to your skivvies.

Style Thoughts Underwear BoggiKronisMack WeldonSunspel

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