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Once known as the go-to skirt for office dress codes and courtroom dramas, the pencil skirt has officially entered its cool girl era. No longer stiff or strictly business, today’s versions are stretchy, curve-hugging and comfortable enough to wear all day — from that 10 a.m. meeting to a 7 p.m. second date.
If you’ve been avoiding pencil skirts because you thought they were too tight, too formal or just not your style, it might be time to try again. We found a mix of polished and flattering pencil skirts that feel as good as they look. Our picks ahead are designed to flatter without squeezing or sacrificing comfort.
10 Versatile Pencil Skirts That Define Your Waist
1. Everyday Icon: This Amazon bestseller comes in 27 colors, hugs your curves in the best way and has just enough stretch to make it an everyday go-to — not just an office-only option.
2. Hamptons Hourglass: This skirts’ ruffled fishtail hem gives serious leg-lengthening energy, while the stretchy fit means you can actually move, squat, sit and walk fast. Very rich mom coded.
3. Matching Set Energy: Take the guesswork out of your going out ‘fit with this ribbed two-piece set. It comes with a crop tank and a high-waisted skirt with a spicy slit — perfect for warm nights or occasions when you want to give body.
4. Adjustable Baddie: This stretchy ruched skirt can go long or short depending on your vibe. It’s classy, cute and the ruching makes it easy to style without showing every little thing.
5. Tie Game Strong: If you’re curvy or want to look curvier, this tie-waist skirt is the one. The side tie adds shape and conceals the tummy area, while the fit is polished enough for a desk-to-drinks outfit.
6. Fun Florals: The soft fabric, subtle sheen and flattering fit make this skirt perfect for brunch or daytime events. It doesn’t cling too tight and the floral print gives easy, elegant vibes.
7. Broadway Royalty: Meghan Markle wore something just like this houndstooth skirt in NYC, and this under-$20 Amazon pick has the same classic polish without the royal budget.
8. Clueless Comeback: Cher and Dionne would 100% approve of this plaid printed skirt. It’s nostalgic, but the stretchy, curve-hugging fit makes it feel current and versatile.
9. Gallery Date: This abstract printed pencil skirt gives major art gallery date energy. The fit and color palette make it look way more expensive than it is — it’s basically the Burberry dupe you weren’t looking for.
10. Sleek in the City: This maxi pencil skirt is stretchy, sleek and surprisingly comfortable.
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