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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36 Responses
Hello!
It’s been a while since skirts have had a place in my wardrobe. Lots of good examples of how to wear them in this post! I like the Q&A at the end.
Yes, because of a super busy fall, I am actually starting to think about holiday gifting. I absolutely love your gift guides and am looking forward to seeing yours this year! I’m hoping there will be a few travel related ones! I also really loved your strategy of sharing one a week and starting early (October) I think, and sharing one a week, if I recall correctly.
Thanks for taking me virtually along on your trip; I enjoyed all of it!
Yeah, I think I will keep that format this year. I like it better than doing them all at once.
Welcome home! I love skirts! Even though they aren’t one and done like a dress, I find so many dresses are shapeless. With a skirt I get the femininity with the ability to have a waist and a more fitted top.
I need you to help me style some!
You have a wide variety of skirt pictures reflecting different lengths that are trending (love the pictures because they show shoe/boot options that look good and on trend). Great guide.
Very fun post, thank you! Love the ideas in here! Welcome home & thank you for taking us along on your trip. 🩷
Enjoyed yesterday’s post about what you wore in Iceland/Scotland. We are considering Alaska and it will be a useful guide.
Love skirts and used to wear them all the time when before I stayed home with my boys, but I wore pencil skirts. Considering trying a couple of the corduroy and denim midis that you featured.
Would like to see you try on black ponte pants in different price points. Would also like to see options for the three Holiday luncheons I have on my calendar. Jeans and a sweater are not acceptable.
Ugh, I have tried so many ponte pants and they make me cranky. They never fit me well. Why are they all so tight in the waist? Maybe I can find the pictures of the ones I’ve tried and put a post together from that. I will definitely add what to wear to a holiday event with jeans aren’t appropriate to my editorial calendar!
Maybe that is why I can’t find any ponte pants that I like. I tried the Vince Pintuck Pleat Crop Flare pants and liked the way they looked, but my hesitation is the price because I don’t think I will them very often. The Vince pants ran small, IMO, and I thought they were tight in the waist. I also tried the Spanx pants and disliked them.
I’m in a couple of clubs that meet at a country club and jeans don’t seem appropriate. I wear dresses in the spring and fall but can’t figure out what to wear in the Jan.-March which is why I thought of black pants. Maybe I should find a skirt and boots.
The struggle is real! The current trend is the baggier pants, and they don’t have to be black or ponte. Like this or this.
Welcome home and great post! It’s fun to see skirts coming back. Would love to see how you are styling your western boots from the Nordstrom sale.
Welcome home! I’m wondering if your adult children were more excited than Savannah was to see you. I am not a skirt woman. I bought a denim skirt last year, tried it on and just didn’t like it on me, so I returned it.
LOL, I don’t think our adult children missed us one iota. Of course, they’re too polite to say so, but my guess is they rather enjoyed having the house to themselves. They actually co-exist quite well together. Caroline cooked and meal-planned, and David chipped in for groceries. I think we should go away more often!
I am sure you’re happy to be home! What an amazing trip. I even brought my husband over to my laptop when I had your Iceland photos up on Insta. We were both impressed and inspired! (He liked Paul’s green jacket!)
Skirts are a favorite of mine, all lengths, but mostly midi. All my tall boots are still up in the attic, can’t wait to bring them down to wear with those skirts. I also love ankle boots with maxi shirts and jeans. I wasn’t sure I would like the midi skirt/ankle boot with several inches of leg showing, but I really do!! I love skirts to wear with my favorite cardigans, lightweight jackets and blazers! Bring them on!
Welcome home! I loved following you on your journey to Iceland and Scotland, England. Such beautiful pictures. And I really appreciate your packing strategies. Great information!! Not sure I’ll ever get to any of your destinations, but England is definitely on my big life list.
As for skirts, I have the brown Loft skirt and leaf print top from ever Eve. I love that outfit. Perfect for late summer/early fall. However, the other longer midi skirts make me look like an Amish person lol. I’m not a fan and will stick to dress pants for the office. I’m 5’4″ and never felt comfortable in skirts. I also wouldn’t get enough wear from tall boots so that investment is a pass. Thank you so much for keeping us updated. Your hard work is very much appreciated !!
Elly, I feel your pain! I’m 5’3 and skirts really are so much trickier as a petite! I love the maxi lengths on others but I agree they make me feel frumpy. As a rule I feel that skirts/dresses above the knee are most flattering proportionately on me. However, I’ve noticed a couple distinctions that help me wear the midi length without looking dumpy. First, I’ve noticed a difference based on fabric. Soft fabrics that drape well tend to work better at the midi length for me than more structured ones. Denim, corduroy, etc, tend to overwhelm me at that length (although I can wear them in a shorter dress or skirt). And second, I think midis that are either fitted or drape close to the body are less overwhelming on my frame than boxier skirts/dresses at this length. Like a silk skirt that just skims, versus a boxy denim one or a flowy cotton one with lots of fabric. I fully understand if you still prefer to skip this trend! Just wanted to share in case you or any other petite ladies might benefit from these observations!
Love your skirts post! Can you come up with some tights choices for the new chocolate brown selections?
Sure, I linked this pair. If you want a more upscale brand, Falke and Wolford both make a pair.
Thanks for all the great ideas for styling. Can you recommend some tall boots for thin calves? I can’t do heels, so need below 2″(flattish is even better). It’s so difficult finding knee boots that don’t gap big time and look silly with skirts and dresses.
Great post, thank you!
What a wonderful trip you’ve had! Your packing posts have helped me, I’m going to London and Ireland in 2 weeks!
I (finally😉) bought a black satin slip skirt and I haven’t worn a skirt in so long I feel I’ve forgotten how! Im in Colorado❄️ I’d love ideas for sweaters, jackets or blouses to pair with it. I’d love to wear it for the holidays. I have knee high suede boots, but they are a wedge (horribly dated?). Im thinking my western boots (have blk and brn). The burgandy slip skirt outfit you styled last year was beautiful!
have so much fun in London and Ireland! Yeah, wedge boots aren’t really a thing at the moment. I would look for a chunky sweater with the satin slip skirt. Or try this one.
💜 thank you!
My favorite is to wear boots with the midi skirt. Love the look!
I love skirts, especially flowy midi and maxi, though I tend to wear them more in the late summer and into fall, more than any other time of year. Why this is, I do not know! Anyhow, I love that burgundy monochromatic look, the two shades are a close but not exact match, and the different textures add that little *something something*. Great post!
Great post as always! I have wanted the Jenni Kayne pleated one for months, but I can never pull the trigger as I dont think I will ever get a good cost per wear. One day I may find it on a great sale 😊
I would love some recommendations for wide calf boots! Thanks. Love the skirts.
I’ll do a roundup!
I love skirts… I have skirts… I buy skirts! I also have a little belly that makes me very self conscious when I wear one! I would love to wear a top tucked in or a bodysuit but don’t feel like it looks good. I tend to wear them with a button-up cardigan which looks cute but would love other options. I can’t be the only one with this issue!! Any suggestions?
I struggle with that too, it’s one reason I tend not to wear skirts much. I don’t have much of a waist anymore, and tucking a bodysuit into a skirt only highlights that. That’s why the outfits I showed wearing skirts, I did more of a front tucked sweater, but I know that isn’t really the trend du jour. I will keep experimenting!
I prefer skirts over dresses (unless its a more formal affair)–they just always seem to stay classic and not fast out of style like a dress can. I like midi skirts–but my fav purchase was a sort of mini (above the knee) from the Loft–a few years ago–I didn’t think I could pull it off–but with tights and boots–perfect. I’m surprised not to see shorter skirts with tights in your selections–I don’t think that look can get old or that older can’t pull it off? Welcome home–your pics from the trip are great–and I am most amazed how you pulled off the packing!
Yes, I mentioned that in the mini skirt section and again in the Q&A at the end. It’s definitely an option, and I don’t think there’s an age limit on that.
I tend to avoid skirts because I don’t like my veiny legs (and they never get tan, no matter what). Then when it gets cold they aren’t warm. So tights are in style this year? I don’t love the new western style boots that are in style this year, nor is suede practical in the rain, which we have a lot of where I live in the PNW. So…should I just ignore skirts till they go away again or is there a good way to keep my legs warm this fall/winter? I also notice you don’t show paid skirts. Are those out right now?
Yes, tights are in style. I mentioned them as an option with shorter skirts. 🙂 I think you meant plaid skirts… I don’t think they’re out, but I don’t see many right now.
I will wear a skirt over a dress 100% of the time. I love separates 🙂
I went to my Pinterest boards to see what I was pinning, and all the skirt looks I like are pencil or A-line with color and pattern! No boring skirts for me. I definitely prefer them styled with heels, sandals, loafers. Boots feel too covered up for some reason. Unless it’s the dead of winter, the look needs some skin.
oh–so when I said I liked boots/tights with a short skirt–I meant low booties–I too, think high boots may be too much.
Ohhh… sorry! Yeah, so it’s not so much a “trendy” look right now, but if the boots and skirt are current styles, I think it could still work.