If I Saw You in Any of These 15 Summer-to-Fall Transition Outfits, I'd Think You Hired a Stylist

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

Paloma Wool

Magalita Crop Crinkle Cotton Blend Button-Up Shirt

WAYF

Maddox Pleated Cuff Trousers

Get the look: Sporty jacket + black flare trousers + open-toe heels

Kallmeyer

Suri Windbreaker in Silk Taffeta

H&M

High-Waist Dress Pants

Get the look: Collared sweater + leather pencil skirt + heeled sandals

Reformation

Hermia Regenerative Merino Polo

Norma Kamali

Straight Skirt

Get the look: Oversized white T-shirt + black denim maxi skirt + flat sandals

Helsa

The Sculpted Tee in Thick Jersey

Get the look: Barn jacket + white sheer dress + cord necklace