I'm an Underwear Snob—These 27 Prime Day Intimates Shockingly Passed My Test

If you're looking for a sign, this is it: Clean out your underwear drawer.
As someone who heavily procrastinates on throwing out too-worn bras and underwear, I can understand the hesitation to let go of comfortable intimates that you've worn for years. (I'm a creature of habit, too!) When I saw this year's Amazon Prime Day deals, though, I knew it was a wrap for the cotton briefs I've had stuck in the back of my underwear drawer since middle school.
For the next two days, some of the most comfortable, well-reviewed underwear, bras, thongs, and boxer shorts are deeply discounted thanks to Amazon's stellar Prime Day deals. Some of our favorite brands, including Calvin Klein and Victoria's Secret are on the table, with deals up to 50% off. Now that I'm turning a new leaf and getting real grown-up underwear, these 27 finds have passed my test of being both cute and comfortable.
Shop the best Amazon Prime Day underwear and bra deals below.
Next, these are the best beauty deals to buy on Amazon Prime Day, chosen by our editors.

Ana Escalante is an award-winning journalist and Gen Z editor known for her sharp takes on fashion and culture. She’s covered everything from Copenhagen Fashion Week to Roe v. Wade protests as the Editorial Assistant at Glamour after earning her journalism degree at the University of Florida in 2021. At Who What Wear, Ana mixes wit with unapologetic commentary in long-form fashion and beauty content, creating pieces that resonate with a digital-first generation. If it’s smart, snarky, and unexpected, chances are her name’s on it.
-
Aritzia Is a Fashion-Person Paradise—These 25 Standouts Are Now On Major Sale
The basics alone are worth checking out.
-
These 31 ClassicReplica Store Anniversary Sale Finds Are the Key to a Rich-Looking Summer Wardrobe
Imagine the chic outfits.
-
It's Now or Never—54 Last-Minute Amazon Prime Day Deals You'll Regret Skipping
Elevated basics, celeb dupes, luxe-like styles, and more on sale.
-
If You Have Amazon Prime Day FOMO, See What Our Fashion and Beauty Editors Actually Bought This Year
The sale ends today.
-
Last Call: These 5 Amazon Prime Deals Are the Best of the Best
It's your last chance to get these amazing styles for less.
-
These Are the Sporty Basics Fashion People Wear for Summer—and They're All on Sale for Amazon Prime Day
Discounted until tomorrow.
-
No Joke: Kate Middleton's Favorite Sneaker Brand Is on Sale for Amazon Prime Day
These shoes are bound to sell out.
-
Just so You Know, *This* Is the Denim Trend New Yorkers Wear With Loafers (Sorry, Skinny Jeans)
And they're on sale right now on Amazon.