That vintage Nanette Lepore skirt deserves better than a one-way ticket to the donation bin, but only if you're willing to stop treating it like a costume. The real issue here isn't the skirt, it's the mental script playing in your head that says high-quality, feminine, and polished automatically equals "corporate lawyer at a luncheon." That script is wrong, and you already know it, because you called the skirt "very pretty" and you're still thinking about it. That's not obligation talking, that's intrigue.
The elasticated waist is your secret weapon, not your limitation. You've already clocked that you can wear it higher or lower, so stop thinking in terms of "how it's supposed to hit" and start thinking about what you want the silhouette to do. If you wear it high-waisted with a cropped, boxy tee in a weird color like rust or chartreuse, you get that late-90s downtown vibe that reads artsy without trying. If you drop it lower on your hips and pair it with a fitted tank and chunky platform boots, suddenly it's not a luncheon skirt, it's a going-out skirt. The fabric is doing the heavy lifting, you just have to stop dressing the rest of your body like you're attending a deposition. And if you're still feeling flight-attendant-adjacent, throw a vintage band tee over it and knot it at the side. Instant chaos, zero corporate energy.
This is the same struggle we saw with that peacock-emerald vintage gem that had a college girl stumped, and honestly, it's the same energy as that burgundy skirt that finally got its moment after years of waiting in the closet. The pattern is clear: we inherit or thrift these pieces that feel "too adult" or "too proper," and we panic because they don't match the eclectic identity we've built. But fashion is not a loyalty test. You can wear a Nanette Lepore skirt and still be the person who owns three pairs of clashing earrings and a leather jacket that smells like every concert you've ever been to. The skirt doesn't erase you, you erase the skirt's default story. If you need more proof that style rules are made to be bent, check out how androgynous style with zero dresses can still feel completely like yourself, it's all about the context you build around the clothes.
Here's the concrete takeaway: wear it with something aggressively "you" in the next 48 hours, even if it's just in your living room, and take a photo. If you still hate it, then pass it along with zero guilt, because you gave it a fair shot. But don't let the fear of looking like someone else's idea of polished keep you from playing with a piece that's genuinely high quality and pretty. The skirt isn't the problem, your imagination is just being lazy. Wake it up.