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.
This Calvin Klein bralette is practically a status symbol, and it's deeply discounted.
If you're not getting the matching panties, what are you doing?
I have this bra already, and I'm stocking up thanks to this incredible deal.
Best believe this Victoria's Secret pair is still bejeweled.
French women love a lacy black bra, and it could be yours too for well under $50.
These ribbed thongs look suspiciously like another brand created by a very famous sister.
Lean into coquettecore with this adorable VS bra.
Sometimes, chic black panties are the easiest yes of all.
The little heart details on this romantic undergarment are my favorite.
I texted all of my friends a link to this bra with three words: "Buy this now."
If you're looking to step up your bra game, look no further than this intricate find.
This one is so timeless, and it's size inclusive.
Wait—I don't think I've been actually obsessed with a thong color palette until I saw this four-pack.
This pack has almost one for every day of the week.
Perfectly seamless under any pair of leggings or workout pants.
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.
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