How to Transition Your Skirts for Fall

September 2, 2022

Skirts are a staple of any wardrobe and can be quite versatile during the fall. Here are some clever ways to wear skirts in the fall and stay comfortable.

When it comes to wardrobe staples I can’t live without, skirts are up there. Regardless of the season, weather, or occasion, I WILL find a way to rock a skirt, from dressing it up with tights and heels to sporting a more casual look with sneakers in the summertime. 

With fall creeping up on us, I’ve been mentally planning all of my cute colder weather outfits in advance. I love skirts because you can usually get away with wearing the same skirt year-round; you just have to get a little creative! Here are some of my favorite ways to transition my skirts for the fall.


Layer, Layer, Layer

Now that the temps will be lower, pair your midi with a long sleeve and a cute cardi to go over for layers. We all know that ’90s y2k is very fashionable right now so why not go with a ruffle-sleeved top/cardi to pair with your skirt?

Speaking of the 90s and y2k fashion, I think shrugs will make a huge comeback. There are so many cute shrugs to be found on Amazon for cheap such as this Shu-Shi shrug that I LOVE wearing for an added layer of coverage. Aside from shrugs and cardis, keep that jean jacket out because nothing looks cuter paired with a skirt (midi skirt, in my opinion) than a jean jacket.

When you pair your midi with a simple top and a jean jacket with Keds, it gives major Joey from Dawson’s Creek vibes and you can’t get more nineties than that! 😉 

Break Out the Midi Skirts

The great thing about those super trendy midi skirts everyone has been wearing is that they can easily be transitioned into fall with no effort. Their longer length means you don’t even have to layer tights underneath–unless you want to. Bonus points if your midi skirt is black or plaid-patterned for a true fall look!

Choose the Right Footwear

The shoes you wear with your skirt can make or break your entire look, so choose wisely this fall. I’m a huge fan of boots in the fall, from combat boots to tall boots and always love a good over-the-knee boot. Boots are always a good move when transitioning your skirts to fall and can be worn with your shortest of skirts to your midi skirts! Don’t forget to try out the sneakers with the midi skirt for a cute casual on-trend look early on this fall. My personal fav for sneakers with midi skirts is either Reebok classics or a platform Ked classic.