4 Stunning Transitional-Weather Looks I Love From the Coolest Fashion People

As a fashion editor, one of my favorite things to do is scroll through the internet to find beautiful looks that inspire me to experiment with my style and try new things. With autumn just around the corner, I’ve been on the hunt for transitional weather outfit inspiration. Among the sea of internet fashion people, I’ve seen some pretty stellar looks that I’m dying to re-create immediately. Since I’m no gatekeeper, I’ve included looks from the coolest fashion people ahead.
Whether you’re looking for outfits that incorporate layering, fun colors, or longer hemlines, I’ve got you covered. You can expect a range of aesthetics from my classic style to vibrant edgy looks. Keep scrolling for the early fall outfit inspiration of your dreams.
There’s something scrumptious about throwing on a lighter jacket or coat to combat the newly landed crisp temperatures. Pair your favorite piece of autumn-friendly outerwear with elevated basics to pull together an easy, classic look.
Pleated midi skirts and long-sleeve tops symbolize the ideal transitional outfit. Opt for easy yet stylish lighter long sleeves and pair with longer skirts for a cool look.
Dronme is the queen of layering. Playing around with light layers can make coming up with transitional outfits even more fun. Try out vests with intricate designs paired with a simple shirtdress/tunic.
Simple doesn’t always mean boring. Here we see a fun black top with gorgeous denim and pointed-toe shoes. Look for simple tops with cool details like cutouts, cropped silhouettes, and fun materials.
Next: I'm Wearing This Versatile Piece All Fall—3 Ways I'm Styling It

Chinazor "Chichi" Offor is a Georgia-born, Los Angeles–based associate editor who relocated from Brooklyn, New York, and joined Who What Wear's West Coast office in 2022. At WWW, she utilizes over 10 years of editorial experience to dish out shopping advice to the masses and analyze key pop-cultural moments. Chichi previously worked at Refinery29, where she helped revolutionize the brand’s plus-size and inclusive fashion coverage. In her spare time, she’s keeping up with the latest movie releases, enjoying a relaxing day at the spa, or obsessing over her latest ADHD-fueled hyperfixation (e.g., Jesse McCartney's underrated career, the negative effects of bicoastal intellectual elitism, and Gen Z’s loneliness epidemic). You can find her online @thechichio on Instagram.
-
The Curvy Girl's Guide to Finding Pants That Fit Flawlessly
Waist gap, begone.
By Shiona Turini
-
The Anti-Trend Shoe Style All of Your Favorite Celebrities Have in Their Closets
Clearly, it's a chic classic.
By Jennifer Camp Forbes
-
How Backyardcore Quietly Took Over Summer Style
The latest dressing trend we're obsessed with.
By Michelle Scanga
-
I Called the Cuffed Jeans Trend—7 Shoes Fashion People Are Wearing With the Chic Denim Style
Style the jeans like a fashion person.
By Jennifer Camp Forbes
-
I Found It: The Non-Denim Skinny-Pant Trend Fashion People Are *Actually* Wearing
Are you ready for this throwback style?
By Michelle Scanga
-
The One Unexpected Piece French Women Are Wearing With Literally Everything This Summer
Chic, sleek, and stylish.
By Michelle Scanga
-
I'm a Stylist in NYC Who Was Just in Paris for 3 Days—These Are the Chic and Easy Outfits I Wore
Elegant looks ahead.
By Bobby Schuessler
-
Spotted on Hailey Bieber: The Chicest Shoe Trend to Wear With Pedal Pushers This Summer
Period.
By Eliza Huber