A Real Guy's Guide to Men’s Underwear | What to Wear (and When)
Most guys stick to one type of underwear. Sometimes because they love it. More often because they just stopped thinking about it.
But not every day is the same. Your underwear shouldn’t be either.
We put together this quick guide to the **most popular men’s underwear styles** based on our own experience trying over 50+ pairs to help you figure out what works best for you, for whatever the day throws at you.
1. Boxers
Ideal day: Lounging Sunday, sleeping, layering under loose pants
Watch outs: Bunching, no support, bulk under slim pants
Classic, roomy, and breathable. Boxers are what most guys switched to as teenagers, and for good reason—they’re comfortable for low-key days but can get bulky under fitted clothes.
2. Boxer Briefs
Ideal day: Any day where you're not sure what to wear or have a little bit of everything, including moderate activity
Watch outs: Ride-up, waistband digging, and leg bands peeking out under shorts
The modern default. Boxer briefs offer coverage and support and work well for most body types. But not all are created equal—fit, fabric, and waistband make all the difference.
3. Trunks
Ideal day: Best underwear for a date night, day at the office with your best tailored suit, weddings, hanging out with your buddies by the lake
Watch outs: Serious ride up if the pair's not right, diaper butt, less thigh coverage
Think of trunks as the middle ground between briefs and boxer briefs. Shorter legs, square-cut, and often a favorite for guys who like a tailored feel without too much fabric.
4. Briefs
Ideal day: Sitting in your office chair or hot days on the court / gym
Watch outs: If it's not a modern cut pair, beware the dad vibes, not everyone loves the exposed leg look
Briefs have made a comeback—for good reason. They stay put, offer freedom of movement, and are the best underwear for hot weather, tighter pants, or guys who just want to avoid bunching altogether.
5. Compression Shorts / Performance Wear
Ideal day: Workouts, running, cycling, sports
Watch outs: Overkill for daily wear, some fabrics trap sweat
Made for movement. Undoubtedly the best underwear for the modern workout. Compression shorts wick sweat, reduce chafing, and keep everything supported during high-output activities. Less ideal for hanging out on the couch.
6. Jockstraps
Ideal day: Gym sessions, high-impact sports, bold confidence (or just because you like how it feels)
Watch outs: Minimal coverage, takes getting used to
The original performance underwear. Jockstraps offer serious support and ventilation. Some guys swear by them for lifting and cardio. Others keep them in rotation just for fun.
7. The "Wildcards"
We see you. These styles have their time and place too. Whether it’s for fun, fashion, or just because you want to switch things up—we’re not here to judge. Every drawer deserves at least one wildcard, and not just shoved in the back of the drawer.
The Bottom Line:
No single style works for every situation. That’s why we built Switchpack: to help guys try different fits without the guesswork or waste.
Your day changes. Your underwear should too.
Switchpack.
Know what you like. Explore what you might.
Want to explore your range -- check out our packs with 2 of the style you like + 2 more that you might