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. Once you discover a pair you actually love, stocking up can get expensive. Prime Day remains one of the best times 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.
If you’re looking for a starting point, prioritize deals from Calvin Klein, a brand that’s remained an underwear heavyweight for decades. Having worn all kinds of styles from the 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.
Best Deal to Grab Now
The standout pick is the Cotton Stretch Boxer Brief 3-Pack, which is discounted 60% off — one of the biggest markdowns across the entire shopping event. This pair is blended with elastane, making it super stretchy and out of the way during leg day. You can squat, lunge, and tackle burpees without any restriction. It also sits comfortably on the waist, provides solid support, and doesn’t soak up sweat during a hard gym session.
At that discount, Prime Day is the ideal time to grab a few multipacks and finally give your underwear drawer the refresh it deserves.
