How to Style Transitional Outfits from Summer to Fall
Summer’s still hanging on—but let’s be real, you’re already eyeing your fall favorites. Whether you’re headed to a late-season beach day, a gameday tailgate, or just want to start layering without melting, transitional dressing is the move. The key? Finding that sweet spot between breezy and cozy. And yes, your wardrobe can (and should) do both.
Let’s talk about how to master that in-between season style—without overhauling your closet.
Start With Lightweight Layers
The secret to transitional outfits? Layers that don’t feel like layers. Think oversized button-downs, cropped cardigans, or light vests you can toss on and take off with ease. Drape them over your favorite tank or mini dress for those chilly mornings and warm afternoons. You get all the fall vibes without fully committing to sweater weather.
Dresses That Can Do Both
That little dress you’ve been living in all summer? Keep it in the rotation. Pair it with ankle boots or tall socks and sneakers, and layer on a denim or utility jacket. Suddenly, it’s giving “I’m ready for pumpkin spice” and “I might still get a tan today.” The same goes for maxi skirts—add a knit tank or a ribbed top and you’re golden.
Gameday But Make It Fall
Tailgates and touchdowns don’t stop for changing seasons. The trick is mixing your spirited staples with autumn textures. Pair your fave team tee or crop top with a pleated mini skirt, then layer with an oversized flannel or bomber. Top it off with sneakers or western boots, and you’re gameday ready—whether you’re watching from the stands or the couch.
Color Shift = Season Shift
Even if the weather’s still warm, switching up your color palette can make your outfit feel more fall-forward. Look for rust, olive, deep navy, mustard, and charcoal. Swap out your brights for more grounded tones—but don’t ditch the fun completely. A pop of red or a bold bag still belongs in September.
Don’t Underestimate Accessories
Add a structured bag, a baseball cap, or even sheer tights to instantly shift a look from summer to pre-fall. Sunglasses still work. So do hoop earrings. And if you’re not ready for full-on boots, a loafer or ballet flat is the perfect in-between step.
Need a little outfit inspo to make it through the seasonal chaos?
We’ve got you covered.
Shop transitional must-haves at SSYS and catch even more styling tips over on our YouTube channel.
Layer smart, style bold.