5 Mom-Approved Outfits for the Transition From Summer to Fall

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It’s mid-August and still 90 degrees in Chicago, yet here I am, counting down the days until Pumpkin Cream Cold Brew comes back 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. Soon, we’ll be chilly and reaching for sweatshirts in the morning but sweating by afternoon.

Knowing how to dress during the transition from summer to fall is definitely a learning process, but you can trust that easy layers, breathable knits, and lightweight jackets will be your best friend during the weather rollercoaster in September and October. We’ve put together five versatile and transitional outfits that will get you through everything from a school drop-off to a morning Starbucks run for your first PSL of the season.

Check out these mom-approved outfits that are perfect for the transition from summer to fall:


1. Denim shorts + basic tee + long cardigan

tee (under $10) / shorts (on sale!) / cardigan / bag / sneakers


2. Graphic tee + leggings + utility jacket

tee (only $10!) / jacket / leggings / backpack / sneakers /



3. Medium-wash jeans + ribbed tank + lightweight blazer

jeans / tank / blazer (under $40) / sandals (only $25!) / hoops


4. Midi dress + denim jacket + sneakers

dress (under $20) / jacket / sneakers /

scrunchie (small business) / sunglasses


5. Sweater tank + pull-on pants + mules 

tank / pants (on sale!) / headband / mules (60% off) / tote

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