Estimated read time2 min read

A GREAT PAIR of underwear won’t get nearly as much attention as a new watch or a fresh pair of sneakers, but it’s arguably the most important piece of clothing you put on every morning. But I’ve found that once I discover a pair I actually love, stocking up can get expensive. As someone who spends a good chunk of the year testing underwear and covering sales, I can tell you Prime Day remains one of the best time to stock up on essentials. And since it’s the only Prime Day sale of the summer, now’s your opportunity to refresh your top drawer.

SHOP CALVIN KLEIN UNDERWEAR DEALS

If I were you, I’d prioritize deals from Calvin Klein, a brand that’s remained an underwear heavyweight for decades. I’ve worn all kinds of styles from the OG label including boxers, boxer briefs, and trunks. The fabrics are soft, the fits are dependable, and the designs are timeless enough that they never feel dated. Today I’d grab the Cotton Stretch Boxer Brief 3-Pack, which are discounted 60% off, probably one of the biggest markdowns I’ve seen across the entire shopping event. This pair is blended with elastane, so it’s super stretchy and doesn’t get in the way during leg day. I can squat, lunge, and tackle burpees without any restriction. Plus, it sits on the waist comfortably, supports my crown jewels, and doesn’t soak up sweat when I’m crushing it in the gym.

The brand’s Knit Boxer, on sale today at 47% off, is just as iconic. The cotton fabric feels so soft against my skin like one of my favorite sweaters. I love fit because it’s roomy, breathable, and gives my goods space to exhale. It doesn’t ride up, pinch, or feel clingy, which is exactly why it’s a longtime favorite. I typically wear them for workouts, office days, long flights, and even lazy Saturdays where I’m just laying around the house.

SHOP CALVIN KLEIN UNDERWEAR DEALS

Headshot of Joseph Cheatham
Joseph Cheatham
Style and Reviews Editor

As the Style and Reviews Editor for Men's Health, Joseph covers all-things fashion and grooming. Previously, Cheatham was a commerce editor for Spy, and he has written for Travel + Leisure.