Skirts are making a comeback this season, and I’ll be the first to admit—they’re not usually my thing. Jeans or pants just feel more practical for everyday, and they’re definitely easier to style. When I need to dress up, I usually reach for a dress because it’s one and done. But as I’ve been watching the new fall trends roll in, I couldn’t help but notice how many cute skirts are showing up. I especially love the way they’re being styled with all the tall boots we’re seeing this year.
Am I suddenly going to give up my jeans for skirts? Probably not. But I do like the idea of having a few in my closet to change things up. So I rounded up some skirts that have caught my eye, along with a few of my older skirt outfits I’d like to recreate for Fall 2025. Hopefully it gives you some inspiration too!
What’s Different About Skirts Now
One of the main reasons skirts are having a moment right now is that they pair so easily with boots. Knee high boots, tall slouchy boots, ankle boots, and even the Mary Jane, ballet flats, and loafer trends all look great with skirts. It’s a way to freshen up your fall outfits.
Plus, fashion right now is very much about mixing textures. I’m seeing suede boots with a satin midi, or a wool skirt styled with a smooth leather bag. Those little contrasts keep an outfit interesting without being over the top.
Best Skirt Styles to Wear in Fall and Winter 2025
1. The Midi Skirt
Midis are everywhere this year, and they’re probably the easiest option if you’re just dipping your toe back into wearing skirts. I like them because they feel current, and they work for both casual and dressier outfits. The key is getting the length right. You don’t want the hem to hit at the widest part of your calf, and if it’s too long it can feel overwhelming. Too short, and it loses that updated vibe. Finding that sweet spot can be tricky, but remember—tailoring is always an option.
2. The Sweater Skirt
Sweater skirts remind me a lot of sweater dresses, which I’ve always enjoyed wearing. They’re stretchy and comfortable, which makes them easy for everyday life. I like that you can keep things simple with a matching sweater for a streamlined look, or switch it up with a shorter cardigan or pullover.
3. The Mini Skirt
Mini skirts are trending again this year, but they can be a little trickier to pull off—especially after 40. The good news is, there are lots of ways to make them feel wearable without looking like you raided your daughter’s closet. If you’re not comfortable showing a lot of leg, try pairing a mini with opaque tights and knee-high or over-the-knee boots. Not only does this add coverage, but it also gives the outfit a chic, balanced look.
4. The Denim Skirt
Of all the skirt styles, denim might be the most wearable. It gives you the same casual vibe as jeans but with a fresh twist, and they pair effortlessly with sweaters and boots for fall. Look for updated details like a front slit or a streamlined A-line shape to keep the look current.
How to Wear Skirts with Boots After 40
Burgundy Satin Midi with Cardigan
Here’s an older outfit I wore where I combined a satin bias-cut midi skirt (similar here) with a simple cardigan and suede boots. I like the monochromatic look and the way the textures play together, and the suede knee boots keep it grounded for fall. If I were styling this today, I’d probably add a chunkier knit on top to make it feel more current, but the overall idea still works.
Black Denim Midi with Turtleneck
This black denim midi skirt is a nice change from the usual blue. I styled it with a deep evergreen turtleneck and tall black boots, which creates a long, streamlined line. I’d probably keep it that simple, but if you like blazers, an oversized tweed style would add great texture and polish to the look.
Denim Skirt with Knee-High Boots
This picture is from a couple years ago, but I still think it’s a good example of how to wear a skirt with boots. I paired this denim midi with tan suede knee-high boots and a simple ivory sweater. The boots add structure and make the outfit warm enough for winter, and I like how the bag ties in with the boots to keep the look cohesive.
Common Questions About Skirts in 2025
I’ve been getting some questions about skirts lately, so I thought I’d answer a bunch of them here.
What length of skirt is best over 50?
Midis are probably the most versatile, but they can be tricky to wear, especially if you’re petite. Getting the length right is key, as mentioned above. Also, don’t be afraid to try a shorter style. I’m starting to see more knee-length options popping up, and minis are popular too. I grabbed the LOFT Twill Mini Pocket Skirt I’m wearing above, and I plan to style it with tights and knee-high boots when the weather cools down.
Can you wear skirts in winter?
Yes, absolutely! The trick is layering. Add opaque tights and tall boots for warmth and comfort, and choose heavier fabrics like wool, denim, or sweater knits that are made for cold weather. And top it all off with a long coat to keep the look balanced and seasonally appropriate.
How do you style skirts with boots?
The key is balancing proportions. For midi or maxi skirts, tall boots work best because they keep the leg line looking long and sleek—just be sure the top of the boot hits under the hem. Mini skirts also pair nicely with knee-high boots since the extra coverage makes them feel more wearable.
To keep the look cohesive, match your boots and skirt in a similar color (and add tights in the same tone if you’re wearing a mini). If you’d rather create contrast, try mixing colors or playing with different textures—like suede boots with a leather skirt—to keep things interesting. Ankle boots can work too, but they don’t feel quite as on-trend this season.
Can you wear skirts with shoes besides boots?
Absolutely! While boots are an easy go-to, you can also style skirts with loafers, ballet flats, heels, or sneakers this fall. You can see my favorite shoes for fall in this post and this post.
Are denim skirts still in style in 2025?
Yes! While I’m definitely seeing a lot of other fabrics taking center stage this year, denim midi and mini skirts are still relevant. They’re an easy option for casual looks, and I love them because they have the same laid-back vibe as jeans but with a fresh twist. Honestly, they’re probably my favorite skirt style to wear in 2025.
Shop More Skirts to Wear with Boots
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