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.
-
Girls That "Get It" in London and Palm Springs Are Wearing This Anti-Denim Pant Trend With Loafers and MulesPlus, they're currently on sale for $60 or less for Cyber Monday.
-
Celebs Love This Specific Denim Style, and It's 40% Off RN—Here Are the Pairs to Buy Before They Sell OutThe most versatile jeans you'll ever own.
-
I Just Saved $767 on an Elevated Winter Wardrobe (Thank You, Amazon)Can't get over these Cyber Monday deals.
-
I Can't Get Over These Chic Reformation Items That Are Temporarily Discounted for Cyber Monday25% off, people!
-
I'd Buy These 45 ElegantReplica Store Investment Pieces Even If They Weren't on Sale (Thankfully, They Are)Deals on deals.
-
I'm a Picky Shopper, But These 30 Shopbop Cyber Monday Finds Have My Seal of ApprovalGet 25% off.
-
I've Had My Eye on These Madewell Pieces for Months—and Now They're Majorly Reduced for Cyber MondayUp to 40% off.
-
If You Missed J.Crew's Black Friday Sale, Don't Fret—You Can Still Score the Chicest Pieces for 50% Off During Cyber MondaySo many great finds.

