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

Transitional dressing [1] 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 centreed 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 [2] 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 favourite fashion influencers [3]. 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 colours, cute prints, and playful accessories.

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POPSUGAR Check Tank Dress [4] ($51, originally $68)

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Susan Alexandra Lisa Bag [5] ($360)

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Lili Claspe Pearl Elizabeth Studs [6] ($100)

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Reebok Princess Classic Shoes [7] ($50)

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Carolina Lemke Wren Sunglasses [8] ($75)

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

Silky camisoles, bright pants, and colourful 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.

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Pixie Market Olive Brown Suit Blazer [9] ($142)

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POPSUGAR Square Neck Cami [10] ($14, originally $36)

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Zara Flowy Pants [11] ($40)

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Maryam Nassir Zadeh Bruno Leather Belt in Pacific Pony [12] ($280)

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Yuzefi Pouchy Bag [13] ($398)

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Sania D'Mina Elena Green Suede Heels [14] ($450)

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.

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Something Navy Leopard Print Water Resistant Coated Trench Coat [15] ($159)

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POPSUGAR Essential Button Down Shirt [16] ($33, originally $44)

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Citizens of Humanity Annina Trouser Jean [17] ($238)

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Dolce Vita Suvi Booties [18] ($160)

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Marc Jacobs Snapshot Camera Bag [19] ($295)

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.

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Anthropologie Marcail Anorak [20] ($160)

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Loft Plus Textured Puff Sleeve Tee [21] ($45)

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POPSUGAR Mini Skirt [22] ($20, originally $50)

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Puma Carina Leather Sneakers [23] ($65)

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Le Specs Air Heart Sunglasses [24] ($69)

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Clare V Herieth Crossbody [25] ($375)

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 mini bag in faux croc.

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Acne Studios Checked Wool-Blend Flannel Blazer [26] ($385)

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POPSUGAR Belted Maxi Dress [27] ($48, originally $64)

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Tibi Nathan Sandals [28] ($575)

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Mango Croc Basket Bag [29] ($60)

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Jenny Bird Harley Hoops [30] ($85)

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

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

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& Other Stories Oversized Cotton Linen Blazer [31] ($129)

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POPSUGAR Midrise Straight-Leg Jeans [32] ($20, originally $50)

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Converse Chuck Taylor Low Top Sneaker [33] ($50)

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Stella and Bow Wilcox Hoops [34] ($65)

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 cosy 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 with sculptural earrings maintain an elevated effect.

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POPSUGAR Long Sleeve Boxy Sweater [35] ($37, originally $50)

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Anna Sui Asymmetric Printed Cotton and Silk-Blend Skirt [36] ($219)

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Adidas By Stella McCartney Adizero Adios Leopard-Bonded Mesh Trainers [37] ($174)

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Moya Jewellery Pruet Drop Earrings [38] ($232)

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 colourful bag in a unique texture like faux croc or snakeprint. For the finishing touch: transparent aviators.

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POPSUGAR Button-Up Midi Dress [39] ($48, originally $64)

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Vans Old Skool Sneakers [40] ($60)

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Nico Giani Adenia Mini Bucket Bag [41] ($390)

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Express Mirrored Gold Metal Frame Aviator Sunglasses [42] ($20, originally $30)

POPSUGAR UK