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 joinedBest Knockoff Luxury Clothing '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 Wholesale Replica Bag 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.
-
Strong, Feminine, and Red Carpet Ready: Sarah Burton Has Hit Her Stride at Givenchy
The designer's sophomore collection is already a hit in Hollywood.
-
I Know I'm Going to See This Specific Parisian Outfit All Over NYC and L.A. This Fall
Expect to see everyone wearing some variation of this easy, cool look.
-
5 Street Style Trends From Milan Fashion Week That Will Be Everywhere This Fall
Take notes.
-
Everyone With Good Taste Is Styling Jeans With This Specific Jacket Style Right Now
You probably already own it.
-
It's Here: The It-Girl Way to Wear a Sweater in 2025
Kendall Jenner just solidified it.
-
Cooler Than a Trench—This Coat Trend Is Quietly Taking Over for Fall
Rich b*tch vibes.
-
Sorry to the Black Pieces in My Closet—I'm Obsessed With This Equally Chic, Classic Color for Fall
Fashion people from London to Paris agree.
-
Cooler Than Leggings—Everyone With Good Taste Is Wearing This Casual Outfit Combo This Fall
Count us in.
-
Suddenly, Everyone With Good Taste Is Styling Their Fall Outfits With This Shoe Trend
See the proof inside.
-
This Dated Denim Pairing Is Suddenly the Chicest Way to Wear Jeans for Fall 2025
Easy and stylish.