Midi Skirts All Day: Why I love Them For Fall/Winter

As someone who’s always loved the unexpected stylish mixture of a dressier piece with something more casual, I honestly can’t get enough of the mid length skirt trend (my favorite way to pair is with sneakers). I have to admit, it can be a difficult trend to make work IRL and I’ve received a lot of questions about it from you guys. I get it- been there. Considering the trend is so here to stay for fall/winter (and even more fun to style), I decided to help a sista out and break it down.

I put together 5 looks including skirts (all available to shop) for a little inspiration.

Nothing says, “I’m cool, I’m here to party and IDGAF (in an effortlessly chic way of course) like a skirt/dress with vans (or sneaks). 


Although I’m wearing tee shirts in these featured looks, I would also pair a good sweater/sweatshirt/long sleeve combination for the transition into Fall/Winter. If you have a favorite dress, try throwing a sweater over top and watch the magic happen!


I love the look of a cool sweatshirt (ordering this one ASAP) and leopard skirt combo, not only because it’s freaking cute but both pieces are extremely wearable and versatile. Topped off with a pair of black booties, gold jewelry and a neutral bag you are good to go. Do not be afraid to pair this with sneakers as well!


Okay, I’m in LOVE with this skirt; it has one of the most flattering cuts in my opinion. The look is served best for winter with a chunky neutral sweater and simple booties, sneakers or knee high boots.





Does anyone else watch the runway videos of the clothing on ASOS before buying? I’m obsessed with this feature! I fell in love with the flow of this adorable button detailed sweater via ASOS runway. Pairing it with the equally precious floral skirt with a slit you cannot see in this photo (please check it out). When a midi skirt has a slit, this is a perfect time for a knee high boot (and I haven’t worn mine in YEARS).



Holiday party, mall shopping, you name it, this skirt can make it happen. I love the sweet yet sexy look of a waist tie sweater over this slip skirt for an evening out. The shoes will take it from one notch to the next in my opinion, so if you want things to be a little more laid back, try a cool bootie, for a fancier vibe maybe a killer open toe statement shoe. The options are endless.


This might be my favorite look! I clearly have a thing for cute sweatshirts, so when I saw this sweater skirt I knew it had to be mine. It’s one of those items that will always need a little waist cinching in my opinion, but I’m okay with it. Throw on a cool sweatshirt and tie a jacket around the waist for an uber chic vibe.



tee: paige (similar here)

skirt: derek lam 10 crosby (on MAJOR sale)

shoes: Kenneth cole

sunnies: celine



Which look is your favorite? Let me know in the comments below!


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