Now and Later: 6 Key Pieces for Summer to Fall Transition Outfits

We love summer and fall with equal gusto. No surprise, we really love all the style opportunities that each season brings, but dressing for the in-between time can be tricky. When it’s still hot one day and brisk the next (or changes from hour to hour), your wardrobe has some work to do.

Our Stylists are here to help you navigate the shifting seasons with versatile summer to fall transition outfits. They’ve made it easy, spotlighting 6 essential pieces that shine in summer (now) and fall (later) depending on how you style them. The whole idea is to get as much mileage out of the pieces you love as possible. 

First tip from our Stylists: don’t put away those floral dresses and skirts, lightweight layers and flowy pants just yet! These are the foundational pieces that we’ll be using to put together cute and clever summer to fall outfits.  There’s lots of room to play from there.

“The fall feels like a fresh start. Take a look at your current wardrobe and think about how you can try something new. Add in prints or try a different play on proportion. Have fun with it!” says Alicia Lloyd, our Styling Team Supervisor at Stitch Fix. 

Is that the first hint of a fall breeze we’re feeling? We better get to it.

Chambray shirt outfits for women with bright shorts and sandals or pants

1. Chambray shirt

Now: Pair a chambray shirt with bright shorts and sandals for a subtle contrast in texture and style. Or use it as a layer unbuttoned over tanks and tees

Later: Our Stylists still go for colorful bottoms to punch up a chambray shirt, but in more muted tones. 

Toss on a shacket (shirt + jacket combo) or other midweight outerwear and a favorite pair of fall boots—keep these on hand because they’re a key player in taking summer pieces into fall.


floral skirt outfits featuring jean jacket or cardigan top

2. Floral skirt

Now: A floaty floral skirt is one of our Stylist’s warm weather favorites—it’s about as summery as strolling down the sidewalk with an ice cream cone on a hot day. It’s August perfection with sandals and a sleeveless top. 

Keep a light jacket on standby for when the sun sets.

Later: Florals for fall? Yes! Just add a chunky cardigan and lug-sole boots. Or any boots, really—the contrast of the utilitarian vibes with the sweet print totally works. 


women's outfits with neutral blazer

3. Neutral blazer

Now: It’s rare that our Stylists can’t find something to pair with white denim and a neutral blazer is at the top of the list. It’s that boss-energy piece that gives instant polish. 

A tee or button-down shirt is our top of choice with a blazer in the summer. Let’s keep that laid-back feeling as long as possible.

Later: Easiest transition ever: swap out light or white denim for your favorite dark jeans. 

We love a relaxed blazer with a printed silky top and loafers, but you could add a gorgeous sweater under here too. 


women's outfit with tie waist pants and tank top or striped sweater

4. Tie waist pants

Now: Our Stylists love tie-waist pants for their versatility in any season. Dress them up or wear them with sneakers for running errands. 

Add a structured raffia bag and a tank for a dinner al fresco.

Later: Hello, sweater weather! We’re all about a roomy sweater with the tailored vibes of the pants. A sleek heel takes the whole look to a date night place.


women's outfits featuring moto jacket

5. Moto jacket

Now: A moto jacket is one of those wow items that works with so many other things in warm weather wardrobes—our Stylists often reach for one to finish off a look. 

We especially love a moto with prints on lightweight sheaths or skirts and tops.

Later: Denim makes another appearance here as a classic pairing with a leather jacket. We brought in another fabulous fall boot in black (*makes note to add black boots to next Fix*).


women's outfits featuring dark denim jeans

6. Dark denim

Now: While we’re still in carefree summer mode, our Stylists balance out darker denim with bright, cheery patterns and textures like gingham and raffia.

Later: Boots and sweaters, but make them colorful! Dark denim still gets a jolt from a novelty sweater and maroon boots in an autumnal palette.

Get styled by Stitch Fix for the seasonal transition

Let our Stylists help you find summer to fall transition outfits and get the most out of your wardrobe. Take your style quiz, schedule a Fix, and get ready to receive an array of versatile styles that fit your unique taste. Try on your new outfits in the comfort of your own home. Pay for what you love and send back the rest. Shipping and returns are always free, and there’s no subscription required.

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