I Went on a Quest to Find Pretty, Sexy Underwear That Are Actually Comfortable

Photo: Free People
The first time I slept with someone after getting out of my long-term relationship, I was wearing a pair of underwear that, had I known someone would be seeing them, I would have never, ever donned. They weren't completely horrendous…but they were beige, high-waisted boy shorts. Any of those things on their own could be cute, but the trifecta was like granny panty central. (Luckily it was dark and I only said, "Wait, ignore how ugly my underwear is" twice. Eye roll at myself.)

After that experience—where he totally didn't care about my underwear—I vowed with god as my witness to never wear un-cute underwear again. Because I realized that, while maybe he didn't necessarily care that I wasn't wearing "sexy" underwear, I kinda did. It had been a while since I had felt desirable, and there's something confidence-boosting about wearing a matching set of lacy underthings, even if no one is going to see them.

There's something confidence-boosting about wearing a matching set of lacy underthings, even if no one is going to see them.

But as I began to add racier pieces to my collection, I quickly came to the realization that a lot of sexy underwear is hell-bent on making your nether-regions feel trapped in a cage of elastic and lace. Now, I have done some weird, uncomfortable things in my sartorial endeavors—like purposefully giving myself a wedgie to avoid bodysuit-induced VPL for a first date. (Yeah, and you thought this was going to be a sexy story.) That was legitimately so uncomfortable, and the guy was definitely not worth the discomfort. (Part of the reason why sneakers are the only shoes I will wear on a first date.)

So I went on a quest to find pretty, sexy underwear that's actually comfortable. In particular, I was on the hunt for pieces I could wear without having to adjust myself every five seconds in my WeWork office, that I'd also feel sexy in if I decided to sleep with someone. The best, as Miley would say, of both worlds.

Behold, the fruits of my labor.

Fleur du Mal Luxe Cheeky, $52


Photo: Fleur du Mal

I'm pretty much obsessed with everything Fleur du Mal creates, but this silky getup is one of my favorites. The straps on the underwear are adjustable, so they won't dig into your sides.

Gooseberry Intimates Full On Glam Thong, $45

Photo: Gooseberry Intimates

I never met a high waist I didn't like. This pair of—fine, I'll say it—panties is very stretchy and soft. Plus, the high waist doesn't dig in, which is cause for an IRL praise hands emoji.

Reformation Helena Thong, $15

TBH, this is one of the most comfortable thongs I have ever worn. The lace is incredibly soft, and the mid-rise is very flattering. Plus, they're sustainably made! (P.S.: the matching bra is also quite comfy.)

Lively The Mesh Back Bikini, $10

A solid everyday option, these bikinis from Lively come in an assortment of colors but aren't basic—the entire back is mesh. (I was going to write something about business in the front, party in the back, but I feel like mullets and lingerie just should not go together.)

Free People Get Off My Cloud Undie, $32

Photo: Free People

If only these had been the beige underwear I wore that one fateful night. (Sigh.) They're subtle and pretty and very soft. I'm partial to the tan if I'm wearing these underneath a dress or skirt that's sheer, but the pink and everglade colors are also quite pretty.

PSA: This is how often you need to replace your underwear, according to two gynos.

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