No Matter the Season, I Can Guarantee You'll Dream About These 24 Skirt Outfits

Please don't judge me for what I'm about to tell you, but I am not a pants person. Don't get me wrong—I own them and wear them when necessary, but they're not my favorite. In my opinion, the best type of bottoms you can buy aren't jeans or trousers. In fact, they're skirts.
Skirts are not only more size-inclusive, but they're also way more versatile in terms of styling possibilities. I'm particularly fond of midi skirts, maxi skirts, and pencil skirts alike. Plus, we've seen more and more runway collections feature skirts, further cementing the fact that they are that staple. But if you're still not sold, you'll want to keep reading, as I've done some digging to identify the six most popular skirt trends the fashion set is wearing right now.
Consider these 24 skirt outfit ideas as proof of the superiority of this staple and its year-round staying power.
1. Column Maxi Skirt
What You'll Need: Leather Bomber Jacket + Button-Down Blouse + Belt + Column Maxi Skirt + Boots
While column skirts may have been popular in the '90s, the way we've seen this skirt styled in the last few months is in no way dated. Case in point? The outfit above. A minimal black maxi paired with a button-down and leather bomber is as timeless as ever.
What You'll Need: White Motorcycle Jacket + Pink Bandeau Top + Flower Choker + Pink Column Maxi Skirt + White Pointy Heels
For an even trendier way to wear this skirt, opt for an iteration in one of the biggest colors of the moment (ahem, pink).
What You'll Need: Cropped Turtleneck + Shoulder Bag + Belt + Column Maxi Skirt + Platform Boots
Another way to make this skirt the center of the look is by styling it with contrasting neutral pieces.
What You'll Need: Turtleneck Sweater + Cardigan + Heart Necklace + Belt + Column Maxi Skirt + Ballet Flats
Lean into the skirt's minimal silhouette by keeping your styling simple. An all-black look with touches of silver and gray will make this skirt the focal point.
2. Pleated Skirt
What You'll Need: Shearling Jacket + Red Shoulder Bag + Mixed-Plaid Box-Pleat Skirt + Knee-High Boots
All things alt inspired have made a serious comeback, including the punk staple: pleated plaid skirts. Play with your styling if you want to make this skirt feel less grungy. Opt for more "polished" pieces like a matching shearling jacket, knee-high boots, and an elegant shoulder bag.
What You'll Need: Leather Jacket + Chain Necklace + Sweater + Long Plaid Skirt + Leggings + Ankle Boots
Lean into the vibe wholly by styling your skirt with quirkier pieces like a cutout sweater or mixed-media jacket. The key to pulling off the look is to keep the colors in the same wheelhouse.
What You'll Need: Sunglasses + White Button-Down + Box-Pleat Midi Skirt + Sneakers + Woven Tote
Not into grunge? Another way you can wear pleated skirts is by going the preppy route. Pair an oversize button-down with a matching pleated midi skirt and sneakers like the outfit above for a more approachable everyday look.
What You'll Need: Cropped Jacket + Pleated Skirt + Socks + Pumps + Black Handbag
When in doubt, keep it simple. Pair your pleated skirt with a cropped jacket and pumps for a look that's equal parts chic and cool.
3. Denim Skirt
What You'll Need: Faux-Fur Coat + T-Shirt + Denim Maxi Skirt + Tights + Pointed Mules
You know denim skirts are back when you see the French fashion set donning the formerly "dated" trend (see above). When paired with a T-shirt, faux fur, tights, and slingback heels, the style becomes the visual definition of chic. Pro tip: Simply remove the tights and coat, and you've got the perfect outfit for warmer weather too.
What You'll Need: Denim Jacket + Denim A-Line Skirt + Denim Bag + Brown Knee-High Pointed Boots
It's not just the French fashion set that's been donning denim skirts. Our very own editor, Anna LaPlaca, has too. Recently, she wore an A-line denim skirt with a matching jacket, bag, and contrasting boots, and it convinced us all that denim skirts deserve a place in our daily lives.
What You'll Need: Leather Bomber Jacket + T-Shirt + Denim Maxi Skirt + Knee-High Boots
What better way to dress up your denim than in skirt form? Pair a white maxi denim skirt with a matching tank, a black leather bomber, and boots for a more spruced-up way to wear this trend.
What You'll Need: Colorful Puffer Vest + Printed Second-Skin Turtleneck Top + Denim Skirt + Neon Pumps
Try pairing a denim skirt with a printed turtleneck and a colorful puffer vest for a cold weather–friendly look.
4. Cargo Skirt
What You'll Need: Shoulder Bag + T-Shirt + Cargo Maxi Skirt + Sneakers
You most likely knew that cargo pants were coming back, but did you know skirt versions were too? We've seen fashion people easily introduce this skirt into their outfit rotations by pairing it with everyday staples (e.g., a T-shirt and sneakers).
What You'll Need: Utility Jacket + Cargo Skirt + Sneakers + Handbag
Lean into the pragmatic nature of this skirt by styling it with sneakers and a contrasting utility jacket.
What You'll Need: Shoulder Bag + Sweatshirt + Utility Vest + Cargo Skirt + Socks + Sneakers
Ready to embrace the gorpcore aesthetic that's been dominating TikTok? Try pairing a cargo skirt with a sweatshirt, a vest, and sneakers for a look that feels hiking-ready without the extra legwork.
What You'll Need: Trench Coat + T-Shirt + Cargo Miniskirt + Knee-High Boots + Clutch Bag
If you're not outdoorsy, you don't have to shy away from wearing this skirt. Just take a more formal approach to styling the skirt by pairing it with the city dweller's beloved staples—a trench coat, a T-shirt, and knee-high boots.
5. Low-Rise Skirt
What You'll Need: Crop Top + Necklace + Low-Rise Black Skirt + Knee-High Boots
Low-rise pants may not be a crowd-pleaser, but low-rise skirts are something else entirely. The fashion set has embraced this style over the past few months as a going-out staple. All you have to do is pair it with a crop top and boots, and you're ready for wherever the night takes you.
What You'll Need: Shearling Jacket + T-Shirt + Low-Rise Miniskirt + Wedge Boots
Playing with proportions is a simple way to ease yourself into wearing a low-rise skirt. A "risqué" mini can feel more approachable when paired with a long tank, a shearling coat, and boots.
What You'll Need: Floral Top + Low-Slung Skirt + Mules
Another way you can make this skirt feel less scary is by styling it with ultra-pretty pieces. A low-slung skirt suddenly feels welcoming when worn with a floral top and mules.
What You'll Need: Printed Crop Cardigan + Skinny Black Scarf + Low-Rise Black Knee-Length Skirt + Boots
If you're not afraid of this trend, why not fully put your skin in the game? Pair a low-slung skirt with a cropped cardigan, a skinny scarf, and knee-high boots for a look that makes taking risks worthwhile.
6. Little Black Miniskirt
What You'll Need: Blazer + T-Shirt + Button-Down + Black Miniskirt + Socks + Chunky Loafers
It's no secret that miniskirts were having a moment, and while we've seen longer hemlines get more buzz recently, it doesn't mean this style is out. A tiny black miniskirt will always be chic, especially when paired with other cool pieces, such as a blazer, a button-down, a T-shirt, and loafers.
What You'll Need: Leather Motorcycle Jacket + T-Shirt + Black Miniskirt + Knee-High Boots
Don't want this staple to feel stale? Style it with a motorcycle jacket, a T-shirt, and knee-high boots for an edgy yet effortless ensemble.
What You'll Need: Varsity Bomber Jacket + Crew-Neck Sweater + Black Miniskirt + Socks + Silver Slingback Heels
Sporty yet cool. Add a vintage or new varsity jacket to a miniskirt and some fun socks.
What You'll Need: Shearling Jacket + Turtleneck + Black Miniskirt + Tights + Knee-High Boots
Consider this final proof that you don't have to wait until spring to wear a skirt. The secret to pulling off this staple year-round comes back to being comfortable enough to play with your styling. Pairing a black miniskirt with tights, boots, a turtleneck, and a shearling jacket is practical and the perfect way to ditch your pants.
This post was originally published at an earlier date and has since been updated. Next up, Fact: Every Summer Look That Screams "Old Money" Includes This One Ingredient
Jasmine Fox-Suliaman is a freelance writer and editor living in New York City. What began as a pastime (blogging on Tumblr) transformed into a lifelong passion for unveiling the connection between fashion and culture on the internet and in real life. Over the last decade, she's melded her extensive edit and social background to various on-staff positions at Who What Wear, MyDomaine, and Byrdie. More recently, she’s become a freelance contributor to other publications including Vogue, Editorialist, and The Cut. Off the clock, you can find her clutching her cell phone as she's constantly scrolling through TikTok and The RealReal, in search of the next cool thing.
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