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transition summer to fall outfit ideas

Autumn On My Mind: Transitioning from Summer to Fall Outfits

transition summer to fall outfit ideas

Let’s be real: Chicago locals know that when it comes to picking a season, it’s actually all about Fall. It’s the first time in a long time when all the tourists stay home and we can actually enjoy this beautiful city. Of course we’ll miss the summer temps, and the weather changing is a bittersweet feeling. But Chicago is a dream in the fall: less crowds in all our favorite spots, perfect weather that turns the trees the most beautiful colors, and a runway of cute & casual fashion! You’d be hard pressed to find a prettier backdrop than Chicago from September to November!

Of course, this leaves the question of how to transition your wardrobe from summer to fall with all of your favorite summer pieces.  It’s still too soon to pack up everything now… we still have several warm days ahead of us! But don’t act like you’re not excited to dig those cozier items out of your suitcase!! Despite the weather being as unpredictable as ever right now, here’s some of the outfits we can’t wait to throw on this fall!

Summer to Fall Outfit Ideas

1. Long Sleeve + Bralette + Jean Shorts

summer to fall outfit ideas with green button downlong sleeve button down with bralettesummer to fall outfit ideas

An unexpected transition for the earlier fall months when the temperature still hovers around the 60’s-70’s, pairing summery shorts with a basic long sleeve top allows the look to seem versatile from the tail end of summer to early fall.  And you can’t deny how refreshing it is to see a fall color scheme again, am I right?? And don’t think you have to put your bralettes away when summer ends, because we wear them all year long! The straps peeking out are a little more subtle than the amount of skin we usually show in the summer– but it’s a fun surprise that keeps the outfit casual and cool. 

Get a Criss Cross Bralette here: Criss Cross Bralette in Mint


 2. Basic Tshirt Dress + Long Duster Cardigan + Ankle Boots

transition a black dress into fall with a sweatersimple black tshirt dress and cardigan sweaterhow to wear a dress in the fall

I spy our favorite item from this summer: the Casual Cool Basic Tshirt Dress!!  This dress is too amazing and too versatile to only wear for one season! Cover up a bit with a trendy cardigan — for this particular dress we chose a longer but open duster cardigan for an unexpected play on the hemlines. Booties give this outfit an elevated “I-tried-but-not-too-hard” look, which is perfect because this outfit actually is not that hard AT ALL.  It’s effortless, comfortable, and very easy to wear to almost anything.

Start this look off by getting the dress here: Casual Cool Tshirt Dress in Black


 3.  Slouchy Sweater + Bralette + Jean Shorts + Booties

oversized sweater with bralette for summer to fallsummer to fall outfit: oversized sweater and bralette fall transition sweater with jean shortswear a bralette and sweater

Seriously, what beats a sweater and jean shorts combo?! Could this scream “summer to fall outfit” any louder?? An off the shoulder sweater is perfect for offering the right warmth during those chillier trips to the Riverwalk, a bike ride down the lake path or just hanging around the city! And we told you to not put those bralettes away yet!! We’re OBSESSED with the peek-a-boo lace bralette and sweater combo. It’s a subtle twist of sexy to an otherwise classically comfy look. And it’s not a fall outfit without the booties. Comfy, casual, and cute, this outfit hits the fall wardrobe jackpot!  

Need this bralette?? Yes, you do! Get it here: Soft Lace Racerback Bralette


transition summer to fall outfit ideasWhat is your favorite way to transition your summer wardrobe into the chillier fall days we have ahead? Let us know in the comments!

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