"It’s the start of September and we’re definitely still experiencing summer weather. Yet here I am, celebrating the return of the Pumpkin Cream Cold Brew at Starbucks. If it’s not obvious, I’m obsessed with all things fall—and extremely excited for spooky season, changing leaves, and fall fashion. But this also happens to be the weirdest time of year weather-wise—and picking out summer-to-fall transition outfits is even harder. Soon, we’ll be chilly and reaching for sweatshirts in the morning but sweating by afternoon.
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Knowing how to dress during the transition from summer to fall is definitely a learning process. But you can trust that easy layers, denim, breathable fabrics, and lightweight jackets will be your best friend during the weather rollercoaster in September and October. We’ve put together seven versatile and transitional outfits that will get you through everything from a school drop-off to a day at the office to a morning Starbucks run for your first PSL of the season.
How I styled these summer-to-fall transition outfits
As a girl who has lived in the Midwest her entire life, I am no stranger to changing seasons. I’m especially familiar with experiencing what feels like all four seasons in one day. One major key to a comfortable any transitional outfit is layering. You need to have something to throw on for chilly mornings and nights but be able to take off in the late afternoon sun. Below, you’ll find plenty of layering options, from button-up shirts to light sweaters. Plus, any of these outfits can be modified to fit the weather on any particular day. Simply throw on a light jacket or add a tank underneath to make it your own.
Sweater tank + loose jeans + Mary Jane flats
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1. sweater tank
2. loose jeans
3. Mary Jane flats
4. bag
5. sunglasses
Short-sleeve cardigan + wide-leg pants + studded flats
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1. short-sleeve cardigan
2. wide-leg pants
3. studded flats
4. tote bag
5. silver hoops
Tee + oversized sweater + relaxed denim shorts
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1. basic tee
2. oversized sweater
3. relaxed denim shorts
4. leopard sneakers
5. suede sling bag
Midi dress + gold sneakers + slouchy bag
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1. midi dress | similar dress option
2. gold sneakers
3. slouchy bag
4. claw clip
5. sunglasses
Shirt dress + knee-high boots + headband
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1. shirt dress
2. knee-high boots
3. bag
4. headband
Tank + wide-leg overalls + clogs
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1. tank
2. overalls
3. convertible bag
4. clogs
5. silver necklace
Why You Can Count on Us
The Everygirl Media Group has brought valuable content to our readers for 12+ years. In 2018, The Everymom set out to ensure that all moms know they’re not alone. If you find yourself seeking advice on how to style the latest fashion trend or searching for the best kid-friendly coffee table, we have the answers. And if you’re wondering what’s actually worth it from a sale or looking for a review of the hottest new kids’ product, we’ve got that covered too. From our annual Registry Awards and beloved holiday gift guides to the shopping round-ups you find on our site every day, The Everymom commerce team is well-versed in sifting through thousands of products to curate a digestible list for you. We combine our own experience with in-depth research to bring you a selection that meets our high standards for both fashion and function.
Jessica Welsh, Commerce Editor
As Commerce Editor, Jessica oversees and edits all shopping content on The Everymom—including everything from mom fashion to product reviews. She also writes in-depth styling stories, trend reports, capsule wardrobes, gift guides, and more. She has created editorial content for major brands such as Nordstrom, Old Navy, and Kohl’s, and was previously a regular contributor to The Everygirl. Jessica believes that fashion should be accessible to everyone, so she is very determined to scour the internet for the best looks for less and affordable finds.