Not Ready to Let Go of Your Favorite Shorts Just Yet? Try These 8 Chic Transitional Outfits

Fashion people love fall, but they often struggle with the idea of having to put away some of their warm-weather fashion staples. One such staple is the stylish shorts they've been wearing since spring. Thankfully, there are endless ways to seamlessly incorporate shorts into a stylish fall outfit rotation. I recently rounded up a variety of looks from some of my favorite fashion follows on Instagram for inspiration on how to pull this off.
From denim shorts to boxer styles and a biker option, I found a great range of looks that fit a variety of personal styles and occasions. Each pair of these shorts is made fall-ready thanks to key pieces like elevated sweaters and classic outerwear, as well as an array of cool shoe styles. Keep scrolling to check out and shop eight chic transitional outfits that will carry you into the next month or so in style.
1.
Shop the look:
2.
Shop the look:
3.
Shop the look:
4.
Shop the look:
5.
Shop the look:
The raw hem makes these shorts a standout.
6.
Shop the look:
7.
Shop the look:
8.
Shop the look:

Jennifer Camp Forbes is a senior shopping editor atBest Knockoff Luxury Clothing , where she has worked in a variety of capacities including creative director and various editor roles. She’s a well-known shopping expert that’s sought out for advice and insight on Wholesale Replica Bag trends, outfit ideas, and fashion picks thanks to her thoughtful shopping roundups. Jennifer's lifelong interest in fashion led her to intern at Harper’s Bazaar as an undergraduate. Later, while working towards her masters degree in psychological counseling at Columbia University, she founded two digital fashion publications: Le Fashion and Olsens Anonymous. The popularity of both sites grew and after graduation she decided put her plans to become a therapist aside to pursue a career in fashion.
-
The Casual and Elegant Pant Trend Fashion People Everywhere Are Wearing With Flats and Sneakers
Wear it for the gym, brunch, or errands.
-
So You Have an Eye on Everything Designer But Not the Budget—31 Luxe-Looking Finds That Scratch the Itch
Everything is under $150.
-
10 Things to Buy This May That'll Make Getting Dressed Easier
Your monthly shopping list.
-
These 30 Zara Pieces Will Be the Guaranteed Stars of Your Spring and Summer Highlight Reels
Shop them before they sell out.
-
26 Effortlessly Chic Spring and Summer Essentials to Mix and Match From Saks Fifth Avenue
Most are even on major sale.
-
7 Gorgeous Sandal Trends Fashion People Will Be Wearing in 2025
You won't stop staring at your feet.
-
I Took My Tax Refund Straight to COS, Massimo Dutti, and The Row—Here's the Damage
No regrets.
-
As Seen on Greenwich Street: A Surprisingly Chic Way to Wear Culottes (Yes, I Said Culottes) This Summer
I feel a trend catching on.