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15 of the Trendiest Skirts on Amazon for Work and Play


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A good skirt is worth its weight in gold, but of course, we’d rather not pay bullion prices for the perfect piece to add to our wardrobes. That’s where Amazon comes in, gathering all of the best fashion picks from both designer names and smaller brands in one place, so you have literally hundreds of options to choose from. But, oh… how to narrow it down?

We figured the easiest way to choose some of the chicest skirts available on Amazon is to highlight some of the trendiest options in two categories: best skirts to wear to work, and best skirts to wear, well, wherever you’re having fun! There are even some pieces that function flawlessly for both, so you can be prepared for a full day of looking fabulous with a stylish a.m.-to-p.m. ensemble. Scroll on to check out our fave trendy skirts available now on Amazon!

Best Skirts for Work

Kingfancy Women's Chiffon Pleated Midi Skirt

Kingfancy Women's Pleated Skirt Chiffon Elastic Waist A-Line Midi Length Skirt Beige Flower XL
This lovely midi-length skirt has a comfortable lining and high elastic waist, perfect for pairing with a variety of business-casual tops from spring through autumn.

Belle Poque High Waist A-Line Midi Skirt

Women's High Waist A-Line Midi Skirt Pleated Pockets Skirts with Belt Black-1 Size XL
Belle Poque
An ideal transitional day-to-night piece, this cute bow-waist skirt will look adorable teamed with a button-down blouse at work and a figure-hugging sweater top for date night.

Grace Karin Vintage Chiffon Swing Pleated A-Line Midi Skirt

Womens Classy Vintage Chiffon Swing Pleated A-line Skirt Brown XL
Emanate elegance in this tightly-pleated chiffon skirt, available in a wide variety of solid colors like rich blue-green and jewel-toned purple, along with patterned options like blue flower and light pink floral lace.

Idealsanxun Women's High Waisted Plaid Wool Mini Skirt

IDEALSANXUN Fall Dresses for Women 2022 Fall Outfits Clothes Winter Mini Skirts (Brown New, XL)
This classic wool plaid mini skirt will give ‘Mad Men’ vibes, especially with a black turtleneck on top. Throw on a pair of knee-high boots and you’ll be absolutely exuding ‘boss babe.’

Grace Karin Women's Ruched Knee-Length Business Skirt

GRACE KARIN Womens Elegant Ruched Knee Length Slim Fit Business Skirt Black
Every closet needs a classic knee-length pencil skirt, especially for any comprehensive business-casual wardrobe!

Calvin Klein Women's Petite Skirt

Calvin Klein Women's Skirt, Charcoal, 8 Petite
Calvin Klein
Calvin Klein always brings the classic basics, and this demure knee-length pencil skirt is a perfect example. Wear with strappy sandals in the summer and knee-high boots in the fall!

Belle Poque Women's Stretchy Bodycon Midi Skirt

Belle Poque Women Plus Size Stretchy Bodycon Skirt Wear to Work Office Pencil Skirt XL BP627-1 Black
Belle Poque
This skirt from Belle Poque offers a twist on the traditional pencil skirt with an adorably accented mermaid-style bottom, ruching at the sides and a free included chunky retro belt.

Best Skirts for Play

BTFBM Boho Floral Print Split Ruffle High-Low Skirt

BTFBM Women 2023 Summer Spring Boho Long Skirts Dress Floral Print Elastic Waist Split Ruffle High Low Beach Maxi Skirt(Z-Black, Large)
Now we’re getting to more options for daytime fun and nighttime festivities, beginning with this flirty high-low number that shows a little leg without highlighting anything you don’t want to. This skirt is particularly perfect for sun-drenched days at the beach or boardwalk — just throw it on over a one-piece or bikini top.

Taydey A-Line Pleated Vintage Skirt

Taydey A-Line Pleated Vintage Skirts for Women (S, Small Yellow Flower)
Vintage style is, ironically, timeless, and this skirt will be a timeless piece in your wardrobe collection. There are more conventional options, like floral and solid colors, but also some quirky designs too, like a super-cute London-inspired pattern and a fun cats-in-sunglasses version for any feline lover with a sense of humor.

Urban CoCo Stretchy Flared Mini Skater Skirt

Urban CoCo Women's Basic Versatile Stretchy Flared Casual Mini Skater Skirt (X-Large, Black)
Urban CoCo
We love a skater skirt, and this version truly embodies the classic skater skirt silhouette. It’s available in sizes X-Small to XX-Large, so it’s made to flatter a wide variety of bodies.

DJT Fashion Casual Stretchy Flared Mini Skater Skirt with Shorts

DJT FASHION Women's Casual Mini Flared Pleated Skater Skirt with Shorts Large Wine
Ahh, skorts really take me back to my younger years. There’s nothing more comfortable, functional and stylish than a good skort, and we especially love the eye-catching jewel tones this version is available in, like deep royal blue and emerald green.

Merokeety Boho Pleated A-Line Swing Midi Skirt

MEROKEETY Women's Boho Leopard Print Skirt Pleated A-Line Swing Midi Skirts DarkPink X-Large
Bring a touch of boho to your closet! The soft and lightweight fabric of this midi skirt makes it the ideal pick for sizzling late August days and sunny September afternoons.

Relipop Flared Pleated Mini Skater Skirt with Drawstring

Relipop Women's Floral Flared Short Skirt Polka Dot Pleated Mini Skater Skirt with Drawstring Caramel
This mini ruffled skater skirt is super on-trend and absolutely August chic — we love it paired with a crop top, like in the product photo, or a tucked-in tank and strappy sandals.

Amazon Essentials Women's Classic 5-Pocket Denim Skirt

Amazon Essentials Women's Classic 5-Pocket Denim Skirt (Available in Plus Size), Medium Wash, 18 Plus
Amazon Essentials
With ’90s fashion totally in right now, denim skirts are making a comeback in a major way. This staple from Amazon Essentials falls just above the knee and has a whole bunch of pockets — and available sizes!

Exchic Mesh Layered Tulle Midi Skirt

Women’s Elegant Mesh Layered Tulle Skirt Sheer Tutu Skirt Midi Dress (L, Black)
Serve Carrie Bradshaw realness in this balletcore skirt, which gives a punk-rock twist on the ‘Swan Lake’ aesthetic. There are several cute colors available, but the dark green is especially striking for the summer-to-fall transition season.

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