17 September Outfits That’ll Have You Saying (I’m So Over Summer!)
I don’t know about you, but the second August starts winding down, I’m mentally done with summer clothes.
I’m ready for chocolate brown, plaid, knee-high boots, cozy knits, suede jackets, and all the rich colors that make getting dressed in fall so much more fun.
The only problem? The weather usually hasn’t gotten the memo.
That awkward summer-to-fall stretch can make getting dressed so confusing. It’s still too warm for chunky sweaters and heavy coats, but your sundresses and bright summer outfits suddenly don’t match the mood anymore.
That’s exactly where September outfits come in.
Think lightweight knits with mini skirts, plaid dresses with knee-high boots, chocolate-brown pieces, light-wash jeans paired with autumn layers, and breezy skirts styled in deeper fall colors.
You get all the cozy, “I’m ready for fall” energy without sweating through your outfit by noon.
I found 17 chic September outfits that make transitioning from summer to fall ridiculously easy.
Some are perfect for those still-hot August afternoons, while others give you just enough layering for the first chilly September mornings.
So if you’re officially over summer and ready to romanticize fall before the weather fully cooperates, keep scrolling.
These are the pre-fall outfits I’d start wearing immediately.
15 Pre-Fall Outfit Ideas For Your Most Stylish Autumn Yet
1. Knit Sweater + Plaid Shorts + Leather Boots
Transition into fall’s cozy-chic fashion with this timeless combo.
The relaxed fit sweater and the autumn perfect plaid shorts. This look brings that early autumn comfort for golden hour hangs and pumpkin spice plans with the girls.
It’s early fall outfit you’ll reach for on repeat this season. Don’t forget to stay totally on-trend with every step you take in the Celine Knee High Leather Boots.
2. Mock Tank + Mini Skort + Knee High Boot
Excuse me while we swoon over this effortlessly chic September outfit.
This look is perfect for those late-summer days when you’re craving fall fashion but it’s still too warm for layers. The mock neck tank, suede skort mixed with knee high boots for a laid-back, elevated vibe.
Whether it’s a crisp day out or a stylish night in, this outfit is your go-to for all things fall.
3. Knit Sweater + Knit Vest + Straight Leg Jeans
Welcome fall with open arms in this stylish knitted combo with relaxed light-wash jeans keep the outfit casual and perfect for those warmer pre-fall days.
I especially love this outfit for a casual brunch, coffee date, shopping day, or an early September afternoon when you want to look like fall—even if the weather still feels like summer.
Complete the look with tan pointed-toe heels, a brown suede handbag, a simple leather belt, and oversized sunglasses.
4. Bomber Jacket + High Rise Suede Jeans + Mock Top
Nothing says pre-fall fashion like the cozy autumn tones.
Pair a fitted black cropped tank with relaxed black pants, then throw on a lightweight camel suede-style jacket to bring in those warm autumn tones.
5. Ribbed Sweater + Ribbed Top + High Rise Jeans
Elevate your wardrobe this fall with a cool-girl sweater that’s perfect throw-on-and-go layer for everything from coffee runs to casual meetings. There is something about this look that says “I’m ready to give up the summer basics”.
The ribbed tank adds a feminine touch while the high-rise barrel jeans makes a statement without sacrificing comfort.
It’s a versatile summer-to-fall transitional outfit that works beautifully for late August and September.
6. Button Down Top + Tweed Skirt + Leather Boots
Simple enough for the office, yet chic enough for pre-fall date-night or brunch this combo proves that fall fashion doesn’t have to mean jeans and cardigans—you can start bringing out your favorite boots while balancing them with lighter pieces and shorter hemlines.
7. Maxi Skirt + Floral Top + Kitten Heels
Every great fall wardrobe starts with autumnal tones like plum, mauve, and chocolate tones and this outfit combo do not disappoint. This look is made for golden hour walks and market wanders.
Style it with heels or ballet flats on warmer days, then grab your favorite knee-high boots when it gets chilly.
8. Plaid Maxi Dress + Denim Jacket + Boots
This look is giving playful, moody, golden hour with the girls vibe.
I especially love this outfit for September brunches, early fall dates, farmers’ market mornings, winery trips, or a casual autumn weekend.
It captures that “I’m ready for fall even though it’s still 80 degrees outside” feeling perfectly.
9. Turtleneck Top + Flare Jeans + Boots
This look was made for crisp days when you want to look effortlessly put-together with minimal effort.
The turtleneck offers the perfect balance of warmth and breathability for those crisp autumn days, while the light-wash jeans keep everything appropriate for fall’s transitional weather.
10. Tank Top + Leather Jacket + Plaid Top + Barrel Jeans + Heels
Say hello to your ultimate fall cool-girl September outfit.
I literally don’t need to oversell it- the tan leather jacket has that sleek, edgy everyday throw on vibe and styled with a chic plaid shirt, crop top and baggy jeans, it’s giving chic meets cool girl without trying too hard.
11. Midi Shirt Dress + Boots
Your chic fall wardrobe just found its match with this Plaid Wrap Tie Midi Shirt Dress.
As the weather gets chilly, this dress will give you bit more coverage than your typical summer midi dress while the knee-high boots keep your legs warmer on crisp mornings and cooler evenings.
12. Hooded Cardigan + Crop Top + High Waisted Jeans
If you’re looking for an outfit that is cozy and cute without feeling bulky, this pre-fall outfit is perfect for you!
Pair this sleek hooded cardigan with a seamless crop top and classic jeans for breezy mornings, weekend coffee runs, or just lounging in effortless style.
This is also a great September outfit for those days when the weather can’t decide what season it wants to be.
13. Vested Romper + Heels
The Ninah Button Down Vested Romper is your new summer go-to for a look that’s both playful and polished. Made from sleek suiting fabric, this romper combines the sophistication of a vest with the ease of a romper, making it perfect for days that flow from brunch to rooftop cocktails.
14. Double Breasted Romper + Heels
Power dressing just got a playful twist with the Leighton Colorblock Double Breasted Romper.
15. Plaid Blazer + Crop Top + Distressed Shorts + Boots
Every wardrobe deserves one blazer that just gets it right, and the Signature Glow Plaid Blazer is that piece. Plaid suiting fabric gets a structured fit with padded shoulders and notched lapels for major polish, while a faux breast slip pocket, double breasted button closures, and front flap pockets round out the tailored details.
16. Shirt Sleeve Cardigan + Leather Shorts + Boots
From morning coffee runs to evening hangs, the Soft Launch Short Sleeve Cardigan is ready for your main character moment.
17. Knit Sweater
The Cinnamon Swirl Turtleneck Cable Knit Sweater is everything you want in a statement layer, bold, textured, and effortlessly chic.
