8 Fresh Outfits to Wear During the Summer-to-Fall Transition

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Transitional dressing is one of those topics that's spoken about in fashion, but not always decoded in full. Like, what exactly constitutes a "transitional outfit"? Should a look be centered around Summer essentials or heavier Fall pieces? Are there key components and formulas to know? Furthermore, how does one know when one has nailed a transitional outfit? Who approves these looks? Is there a between-season fairy godmother we can tap to confirm?!

In my opinion, the short answer is: there are no rules when it comes to transitional dressing! Anything goes! Do you! However, there are a few key styling tips that are helpful for every woman to master, from the jackets and sweaters that are best for layering over dresses to the types of boots that effortlessly extend the life of summery separates and textured extras that help make lightweight pieces feel Fall appropriate.

So, to prepare you for the in-between season, ahead, I'm breaking down eight transitional outfits that are A) perfect for Summer-to-Fall weather, B) fresh and fun, and C) inspired by some of my favorite fashion influencers. Exciting, yeah?! To make the deal even sweeter, I've shopped out each transitional outfit with similar styles that range from affordable finds to investment-worthy pieces. You've got this.


The Summer-to-Fall Outfit: A Blazer + Minidress

Take lightweight minidresses into Fall by layering a textured blazer over top. Keep things fun and cheerful by opting for bright colors, cute prints, and playful accessories.


The Summer-to-Fall Outfit: A Tank Top + Blazer + Pants

Silky camisoles, bright pants, and colorful accessories are Summer staples, but you can easily take them into Fall by layering a tailored coat or blazer on top. When mixing several punchy shades together, be sure to ground the look with a few neutral pieces.


The Summer-to-Fall Outfit: A Trench Coat + Jeans + Boots

Animal print and '90s denim are two major trends that are continuing for Fall. Lean into both by layering leopard-print pieces together over loose, straight-leg jeans. For an unexpected finish, western boots are the way.


The Summer-to-Fall Outfit: A Miniskirt + Jacket + Sneakers

The easiest way to take a miniskirt into cooler weather? With an anorak jacket and versatile sneakers.

Shop Summer-to-Fall Fashion

Shop Summer-to-Fall Fashion

POPSUGAR Mini Skirt ($20, originally $50)


The Summer-to-Fall Outfit: A Dress + Blazer + Heels

White dresses are hardly exclusive to Summer. For the in-between, style yours with an oversize blazer, cool kitten heels, and a geometric minibag in faux croc.


The Summer-to-Fall Outfit: Jeans + a Blazer + Sneakers

Light denim can totally be worn post-Labor Day. In fact, a pair of off-white jeans look so sharp with a tailored blazer, graphic tee, and Converse sneakers.


The Summer-to-Fall Outfit: A Sweater + A Skirt + Sneakers

A floaty midi skirt works just as well in cool weather as it does on hot days. For a cozy look, try your hand at print-mixing and team a striped knit with a floral print on bottom. Sporty sneakers take the look in an even bolder direction while sculptural earrings maintain an elevated effect.


The Summer-to-Fall Outfit: A Dress + Sneakers + Bag

A printed dress is one of the easiest Summer-to-Fall pieces. Transition yours with a pair of classic Vans and a colorful bag in a unique texture like faux croc or snake print. For the finishing touch: transparent aviators.