It’s time to update your wardrobe with chic yet cozy outfits as summer slowly fades and fall begins to settle in.
The shift from breezy summer pieces to warmer fall layers creates the perfect opportunity to mix light fabrics, rich tones, and stylish transitional silhouettes. So if you’re searching for fresh outfit inspiration to refresh your closet this season, keep scrolling for our guide on what to wear from summer to fall, plus easy styling ideas to pull each look together.
Since most of these outfits focus on just one to three key pieces, you’ll be able to recreate several of these comfy and stylish looks with minimal effort.
Summer to Fall Outfit Ideas
T Shirt + Light Cardigan + Jeans
This combo is a lifesaver. A basic tee keeps things breathable, while a light cardigan adds warmth when the breeze hits. Pair with jeans and sneakers, and you’re good all day.
Midi Dress + Denim Jacket
Not ready to give up your dresses? Same. Just throw on a denim jacket and suddenly your summer dress feels fall-ready. It’s casual, cute, and super comfortable.
Tank Top + Button-Down Shirt
Wear the button-down open during warm afternoons and button it up when it gets cooler. It’s effortless layering without feeling bulky.
Flowy Skirt + Simple Tee
A flowy skirt still works perfectly in early fall. Pair it with a tucked-in tee and sneakers or flats for a comfy, stylish look.
Crop Top + High-Waisted Jeans
This outfit screams “transition season.” It’s still summery on top, cozy on the bottom, and looks great with sneakers or ankle boots.
Short-Sleeve Dress + Ankle Boots
Swap sandals for ankle boots, and suddenly your summer dress feels totally fall-approved. This small change makes a big style difference.
Lightweight Sweater + Denim Shorts
Yes, shorts can stay! Pair them with a lightweight sweater for those warm days with cooler evenings. It’s cozy but still breathable.
Graphic Tee + Oversized Blazer
This is one of my favorite combos. The tee keeps things casual, while the blazer adds a polished, fall-like touch.
Sleeveless Top + Wide-Leg Pants
Wide-leg pants feel breezy yet cozy. Pair them with a sleeveless top and add a light layer if needed.
Casual Jumpsuit + Sneakers
Jumpsuits are a one-and-done outfit. Choose a soft fabric and neutral color, and you’ll feel comfy and stylish without trying.
Maxi Dress + Light Knit Cardigan
Maxi dresses transition beautifully into fall. Add a soft cardigan and you’re ready for coffee dates, errands, or casual outings.
Tank Top + Shacket
Shackets (shirt-jackets) are perfect for this season. They’re not too heavy but add just enough warmth to your outfit.
Simple Top + Paperbag Pants
Paperbag pants are comfy, flattering, and perfect for fall vibes. Pair with a simple top and flats or sneakers.
Denim-on-Denim Look
A denim shirt with jeans might sound bold, but it works beautifully in transition weather. Just keep the shades slightly different.
Casual Romper + Light Layer
Rompers don’t have to disappear yet. Add a cardigan or light jacket and switch to closed-toe shoes.
Easy Tips for Styling Summer to Fall Outfits
- Layer smart, not heavy: Light jackets, cardigans, and shackets are your best friends.
- Switch shoes first: Sneakers, loafers, and ankle boots instantly make outfits feel more fall-like.
- Use warm tones: Beige, brown, olive, rust, and soft neutrals transition beautifully.
- Comfort is key: If you’re comfy, you’ll feel confident—and that always looks stylish.
- Mix seasons: Don’t pack away summer clothes too fast. Mixing pieces is the secret.