It might feel like summer just started (or is that just me?), but whether we like it or not, fall is approaching, and I, for one, don't want to wait until the last minute to start planning my autumn outfit rotation. Instead, I like to get to preparations early—so early, in fact, that I often begin wearing fall pieces when it's still technically summer. Think tissue-thin knits styled with a leather skirt or a lightweight jacket paired with trousers and flip-flops. Transitioning from summer to fall with ease is a fine art, and fortunately for, well, everyone, I follow all the masters at it.
Ahead, prepare to discover the ultimate outfit guide to fall-to-summer transitional outfits in 2025. There are button-down shirts styled with calf-hair skirts, sundresses paired with barn jackets, and car coats styled with V-neck sleeveless shirts and sandals. There is a sartorial science to dressing during that confusing period between late summer and early fall, and the fashion people below have the equation memorized. Keep scrolling if you want to be the next expert on the subject. (Trust me, you do.)
Get the look: Gray button-down shirt + black wide-leg trousers + flip-flops
Get the look: Sporty jacket + black flare trousers + open-toe heels
Get the look: Collared sweater + leather pencil skirt + heeled sandals
Get the look: Oversized white T-shirt + black denim maxi skirt + flat sandals
Get the look: Barn jacket + white sheer dress + cord necklace
Get the look: Eyelet dress + black trousers + heeled sandals + shoulder bag
Get the look: Button-down shirt + calf-hair skirt + tights + kitten-heel pumps
Get the look: Leather blazer + lightweight sweater + lace-trim shorts
Get the look: Red T-shirt + ivory coat + capri pants + flats
Get the look: Crochet top + ivory coat + black trousers + flip-flops
Get the look: White button-down shirt + flare jeans + heeled sandals
Get the look: Black blouse + leather pencil skirt + strappy heels
Get the look: V-neck top + black coat + flare trousers + silver necklace
Get the look: White T-shirt + maxi dress + red flip-flops
Get the look: Trench coat + white T-shirt + wide-leg jeans
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