How to Wear Jean Shorts in the Fall Without Freezing Your Butt Off

In the summer, we practically live in jean shorts. They work with just about everything in our wardrobe, from crop tops to bikinis to street style-approved open dresses. Now that fall is here, we’re not quite ready to give them up. The good news is, we don’t have to. Jean shorts are actually a great transitional piece as we adjust our wardrobes for brisk autumn days. For most of us, style isn’t about getting the most Instagram likes for our #OOTDs. It’s about creatively getting the most mileage from our clothes, which is why we’re wearing white all year long, championing florals for all seasons and rocking boots when we could be wearing sandals. Likewise, the “anything goes” mantra applies to our favorite jean shorts. And we’re certainly not alone. Fashion girls love to flaunt their knack for seasonless dressing, layering seemingly impossible pieces together in a way that just works. The key is to make sure your look is weather-appropriate. (A bralette and jean shorts in December looks painful, not pretty.) For cooler months, think of denim shorts as you would a skirt or dress when crafting your cool-girl transitional wardrobe. In need of some visual guidance? Scroll through the gallery above to see how the fashion set is wearing jean shorts this fall.

Images: Imaxtree

How to Wear Your Favorite Jean Shorts into the Fall

Hoods Up

When it comes to wearing jean shorts on cool days, it's all about the layering. Start with sheer tights under your cutoffs to keep legs toasty. On top, anything goes, but a hoodie worn underneath a bright jacket will do the trick. Box-fresh white sneakers, a vibrant Chanel bag and yellow-tinted sunglasses will work no matter the season.
Camo Denim

A long-sleeve T-shirt and opaque tights serve as the perfect base layer for denim shorts and a camo jacket. On really chilly days, tuck a scarf inside the jacket and leave the tails hanging so they're just visible.
Double Denim

Put a trans-seasonal twist on the Canadian tuxedo by subbing the usual jeans for denim shorts. A lace-trimmed chambray blouse is also more unexpected than the usual jean jacket. Can't get enough denim? Slip on a pair of jean boots for a triple denim look.
All Year Denim

Ditch the T-shirt for something a bit more substantial, like a sweater. Embroidered brogues are the perfect compromise when it's too cool for sandals, but you're not quite ready for boots.
Swap That Blue Denim

Take a cue from off-duty models and trade basic blue jean shorts for black. Team them with a coordinating peacoat, band tee and brimmed hat. Keep the rest of the accessories in the same dark color scheme. Got goosebumps? Add a pair of black sheer tights for some warmth.
Shorts and Stripes

Even the cheekiest of denim shorts can be worn in the fall when paired with a knee-length coat. Play up the blue cutoffs with a classic blue pinstriped coat. Keep toes and ankles toasty with chunky boots and socks.
Winter White

Here's how to wear white and denim all year. Shrug on a comfy white sweater over frayed white jean shorts. Add some balance and warmth with tall boots and knee socks.
Mix and Match

Gucci loafers (or some similar-looking version) were the It shoe of spring and summer. Wear yours into the fall with light-washed denim, a sheer blouse and a statement jacket.
Crops and Shorts

Defy the fashion "rules" by bringing jean shorts and crop tops into September. A leather jacket provides warmth on top, while high-rise mom shorts and thigh-high stockings take care of the bottom. (Although, when you look this hot, you probably don't even feel the cold.)
Next-Level Jean Shorts

The formula of this Tommy Hilfiger Spring 2017 outfit is simple: motorcycle jacket, cropped tee, jean shorts and boots. But it's the standout pieces that take the look to the next level. Customize jean shorts with patches and give that tried-and-true black biker jacket a break every once in a while.
Dressed Up Denim

Take a white T-shirt and washed jean shorts from day to evening by topping them with a velvet blazer and boots. For an It girl-approved look, select a jacket and boots in contrasting jewel tones. A Gucci belt and statement drop earrings will work no matter what time of day it is.
Mix Master

Make some room for white denim shorts in that fall wardrobe. Denim of any color works into fall when it's worn with tall boots and a sweater, but white feels particularly fresh. Opt for a Kimye-approved sweater or embrace logomania with a designer one.
Bringing Basics Back

Stop treating "wardrobe basics" as dirty words and style those jean shorts with black tights, a billowy white tank top and no-fail black ankle boots. On days when the forecast changes from hour to hour, wear a long cardigan, but keep a shorter version (literally) on hand.
It Girl Approved

Bring all the cool-girl wardrobe staples together by mixing a black motorcycle jacket, cropped T-shirt and ankle boots. A bandana and thigh-high tights up the It girl factor while covering up exposed skin from brisk fall winds.
Polished and Pretty

If Chiara Ferragni can wear jean shorts after Labor Day, so can the rest of us. Take inspiration from the style star by sporting a soft blazer with dark denim shorts for a polished look. Keep the jacket from looking corporate by exposing a hint of a matching bralette. A fanny pack and black over-the-knee boots make it clear you're not heading to a Monday morning meeting.