When it comes to early fall, there's so much to love. The weather is perfect—not too hot, not too chilly—and in terms of getting dressed, it's prime time for busting out all of our favorite transitional pieces. Personally, I'm excited to bring my denim jackets out from the back of my closet and snag a few new ones for my collection while I'm at it. They're just so easy to wear, and I consider them one of my outerwear go-tos during the in-between seasons.
After scouring Instagram for some good fall outfit inspiration, I noticed that styling them with skirts just might be the look for fall. Jean jackets and skirts—from slinky midis and maxis to matching denim minis—are the combo fashion people are currently loving.
To help kick off jacket season with a bang, I rounded up some of the best looks I came across. Keep scrolling for the chicest ways to wear jean jackets with skirts—and, of course, shop the top pieces of the season.
We're big fans of cropped denim jackets. They're great layering pieces, especially when worn closed over a longer top. Pairing one with a flowing, pleated skirt like the above can really elevate a casual look.
Ganni always gets it right. Can we talk about this collar?
The basic white tee, but better.
A pleated black midi skirt is always a good wardrobe standby.
Take your Canadian tuxedo to the next level by pairing a classic denim jacket with a patchwork denim midi skirt.
For warmer weather, opt for a lightweight shacket.
I need this skirt immediately.
These gorgeous leather slides are buttery soft. I'll be pairing mine with a cute pair of socks once the weather gets chilly.
A denim jacket can make any summery look—like this super-cute tank-and-miniskirt combo—more fall-appropriate.
You can't go wrong with classic blue denim.
Slim-fit tank tops look great under denim, just saying.
I love a good fall floral.
A matching denim jacket-and-skirt set is casual yet polished. This look in particular is perfect for end-of-summer weather.
Quilting is having a moment this fall, making this denim jacket a must.
And there's a matching skirt.
I’m a big fan of pairing skirts with sneakers, and Air Force 1s are the one style I never get tired of.
Hear me out: Layering skirts over pants may not be for everyone, but this look is expertly executed—and the light-wash denim really ups the cool factor.
This staple jacket is made from organic cotton and comes in two different washes.
A tweed skirt is peak fall fashion.
Loafers are *the* shoes for fall, and this chunky mule style is a great option.
In my opinion, white denim looks chic any time of year. A matching set makes it that much better.
I love the oversize fit of this jacket.
If there's one basic you should buy for fall, it's this mock-neck bodysuit.
This skirt would look so good with a pair of chunky knee-high boots.
A silky printed midi skirt can make any denim jacket feel dressier. Take the above look, for example.
This simple denim jacket is timeless. Bonus points for the fact that it's affordable, too.
This print, though.
Low-heel mules are the perfect year-round sandals.
Layering prints can be tricky, but an oversize denim jacket can help tone down the busyness. This patchwork coat, in particular, is an excellent choice (as are the solid neon accessories).
If there's one denim jacket I buy this season, it'll be this one.
A cute knit crop top makes a denim jacket feel instantly cozier.
Of course, the matching miniskirt is also a must.
Next: 8 Fall Trends NYC Girls Are Actually Wearing
-
Kristen Bell Swears Her Nobody Wants This Character Is Cooler Than HerBut it’s safe to say she would have approved of the actress’s flawless Armani gown for last night’s Emmys.
-
I've Worked in Fashion for 15 Years—Here's What I Actually Wear Every DayTrends come and go, but my everyday wardrobe is made of pieces that feel like me.
-
My Mom Only Shops Affordable Fashion—I Sent Her These 27 Chic Rich-Looking Pieces for Fall 2025Everything is under $100.
-
EverythingBest Knockoff Luxury Clothing Editors Saw, Wore, Did, and Ate During NYFWLet's dive in, shall we?
-
Paris Hilton's World: Her Pink Motorola Razr, Favorite Y2K Looks, and What 11:11 Media Means to HerA glimpse into the life of this savvy entrepreneur.
-
Hold the Brown and Black Jackets—Experienced Shoppers Are Swapping Them for Ones in This Fancy ColorElsa Hosk wouldn't lead us astray.
-
I Popped Into Zara to Shop for a New Fall Jacket—Here's What Came Home With MeSo many chic styles.
-
I'm an NYC Shopping Editor—I Can't Stop Thinking About These 31 Rich-Looking Fall Finds FromReplica Store, Zara, and H&MDid I mention they're under $250?
-
I Live in Murray Hill—Here Are the 8 Places I Like to Shop for a Fashionable Fall ClosetStylish sweaters and suedes ahead.
-
People With Impeccable Taste Swear By COS—21 Chic Sale Finds to Take Advantage of Right NowDid you say 25% off? Yes, please.
