15 Perfect Skirts If Your Style Verges On “Chic Grandmother"
Image from Sézane
by The Candidly Team
If you were going to raid your mother (or grandmother’s) giveaway pile right now, what would you grab? Because, for us, it would be the skirts. Flowy or frocky. Floral or paisley. Maxi or midi.
Keep the slacks. But surrender the skirts.
And that is because skirts used to be good. They were meticulously made to be easy, flattering, and feminine. And, every now and then, they still are.
Find a good, romantic skirt today, throw it on with practically anything, and it all instantly becomes a zillion times more interesting. Just look.
And because it’s not trendy, it remains chic decade after decade. As proven by the quintessential coastal grandmother herself.
And so, for those of us who see the appeal of matching irreplaceable originality with herb gardens, antique florals, comfy shoes, and afternoon tea, we made it our mission to seek out skirts that capture all the classic, spirited allure that comes with being “grandmother chic.”
We found 15.
1. J. Crew Smocked-waist cotton voile midi skirt
A smocked waist might be the principal feature required to make a flowy midi skirt 20X more comfortable and flattering. This one is an airy cotton that adds zero bulk. And it sizes up to 3X.
Price: $138
2. Sézane Dilona Skirt
This skirt is from one of our favorite French brands, so naturally we dream of throwing it on with comfy sandals and storming around the Cote d’Azur, but (perhaps more realistically), we also plan on wearing it to every wedding we’re invited to this year. The soft pleating, subtle flare, and nipping high-waist make it not just a pretty print but a breathtaking fit.
Price: $170
3. By Anthropologie Sleek A-Line Skirt
We had trouble choosing from the sea of prints and solids that this supremely flattering, fun-to-wear skirt comes in. Honestly, you could pair any one of them with strappy sandals and a stretchy tank, and you’ll have mastered a foolproof summer uniform. Plus, pockets! Several of the styles come in plus and petite, and it’s machine washable, thank the lord!
Price: $120
4. Boden Full Printed Maxi Skirt
A chic, long maxi is the style piece that weirdly eludes us. After years of searching, we found THE prettiest one. In pink!
Price: $198
5. Favorite Daughter The Gwen Floral Maxi Skirt
Forget that it lengthens you for days and fits like a curve-loving dream, we’re just here because we know there will never be a day we pull this skirt from our bummer of a closet and don’t answer, “Yes, this sparks joy.”
Price: $218
6. Hill House The Delphine Nap Skirt
So, Hill House is of course the brand with this magical dress that “broke the Internet.” Which makes sense. Because it’s unbelievably flattering. In no small part because of the smocking. And this skirt, with its long stretch of stomach-smoothing smocking, is just as special, if not more so. Plus, the prints are the stuff of grandmother-chic dreams.
Price: $125
7. Ba&sh Neo. Maxi Skirt
And here we have the “nice” skirt - the formal, eye-catching, enviable maxi that makes us look carefree and chic and 70s and 6ft tall. Wear it with THIS curve-flattering bodysuit and THESE flat, minimalist flips, and you will look spectacularly “together,” despite having taken 37 seconds to get dressed.
Price: $325
8. J. Crew Side-Slit Soft Gauze Maxi Skirt
We don’t always fall in love with the styling of J. Crew (though on their own, there are a ton of truly cut-above, wear-all-the-time pieces on their website). This skirt, with its light, airy, pajama-like feel and lovely fit, is one of them. And we actually do love it as pictured with a tied-up button-down. Though we’d swap the heels for #3 on THIS list.
Price: $89.50
9. Veronica Beard Serence Paisley Skirt
This skirt is what you’d call more of an “investment piece.” But we’re believers in the philosophy that buying one great, perfectly made thing you’ll love forever instead of 18 cheap, fraying, subpar versions of that thing is better. This skirt is slightly boho, spun from a light cotton voile, has a stunning slit, and an overall silhouette that just never stops looking gorgeous on our bodies. And the print is sheer perfection.
Price: $398
10. Boden Shirred Waist Linen Midi Skirt
Nothing is more comfortable (or flattering) round our waistline than a thick band of blessèd smocking. Except perhaps this English seaside color.
Price: $128
11. Faherty Dream Cotton Gauze Valentina Skirt
Perhaps the easiest skirt on this list. It’s soft and light and feels like loungewear, but the print is pretty enough to dress it up or down and wear it everywhere. You can’t go wrong pairing it with a favorite white tee and THESE chic slides, but what really completes your Coastal Grandmother ensemble is THIS basket bag.
Price: $148
12. Petal & Pup Ayla Skirt
This is the sort of skirt we turn to when we want something a bit more statement and voluminous, making it perfect for spring and summer “occasions.” It’s a spacious and romantic alternative to all those disappointing, restrictive dresses we’re forced to fasten ourselves into every time we want to look truly “dressed up.”
Price: $89
13. J. Crew Pull-on maxi skirt in luster crepe
It’s true that this skirt has sleeker lines and some mildly dressed-up, 90s vibes, but it also has that essential elastic waist and a not-too-tight fit that make it effortless to wear. It looks as good with a fitted tank as it does with a billowy button-down. We really like the boldness of the blue, but the black is a staple we’ll be wearing on repeat…mostly out-to-dinner.
Price: $168
14. Mortilo Women Bohemian Floral Print Skirt
We don’t throw the word show-stopper around very often. But if this skirt doesn’t drown out the world and capture your attention, then we don’t know what will. Except perhaps the price.
Price: $17
15. Free People Simply Smitten Maxi Skirt
Sometimes all we require is a perfect, tiered maxi skirt. That’s soft as a cloud. Ties at the waist. Comes in 37 colors. And looks equally excellent when we’re puttering around the house, baking bread as when we’re basking in some ridiculously glowy sunset, feet covered in sand. Also great for after we consume said loaf of bread.
Price: $78
At The Candidly, we try a lot of stuff so you don’t have to. We only recommend things we truly love, and that we think you’ll love, too. All products are chosen independently by our creative team, and all details reflect the price and availability of products at the time of publication. If you buy something we link to, The Candidly may earn a commission.
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