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.
-
I Never Miss a Good Shopbop Sale—These 39 Chic Summer Finds Are Too Good to Pass Up
Take an extra 25% off.
-
Chic, Elevated, and On Sale—Here's What to Buy From & Other Stories, Madewell, and Saks Right Now
So many good discounts.
-
31 Finds From the Nordstrom Half-Yearly Sale That Are Guaranteed to Make Your Outfits More Fashionable
Bring on the compliments.
-
Here You Go: The Coolest Under-$100 Pieces From the Nordstrom Half-Yearly Sale
Through June 1.
-
Don't Say You Never Knew—These 32 Elevated Nordstrom Basics Are a Steal During the Half-Yearly Sale
Don't mind if I do.
-
I'm a Nordstrom Stylist—This Is Exactly What to Buy From the Half-Yearly Sale
Expert picks.
-
I Trend-Spot for a Living—Here's What Caught My Eye at the Nordstrom Half-Yearly Sale
There are so many good finds.
-
Attention: J.Crew's Sale Has 50% Off Thousands of Styles—I've Whittled It Down to the 33 Chicest Items Worth Adding to Cart
Don't miss out.