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Easy Transitional/Fall Outfit Formulas to Master

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 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 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. 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.

Image Source: Instagram / @oursecondskin

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.

POPSUGAR Check Tank Dress ($51, originally $68)

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POPSUGAR Check Tank Dress
$51
from kohls.com
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Susan Alexandra Lisa Bag ($360)

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Susan Alexandra Lisa Bag
$360
from susanalexandra.com
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Lili Claspe Pearl Elizabeth Studs ($100)

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Lili Claspe Pearl Elizabeth Studs
$100
from liliclaspe.com
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Reebok Princess Classic Shoes ($50)

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Reebok Princess Classic Shoes
$50
from kohls.com
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Carolina Lemke Wren Sunglasses ($75)

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Carolina Lemke Wren Sunglasses
$75
from carolinalemke.com
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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.

Pixie Market Olive Brown Suit Blazer ($142)

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Pixie Market Olive Brown Suit Blazer
$142
from pixiemarket.com
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POPSUGAR Square Neck Cami ($14, originally $36)

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POPSUGAR Square Neck Cami
$14
from kohls.com
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Zara Flowy Pants ($40)

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Zara Flowy Pants
$40
from zara.com
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Maryam Nassir Zadeh Bruno Leather Belt in Pacific Pony ($280)

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Maryam Nassir Zadeh Bruno Leather Belt in Pacific Pony
$280
from needsupply.com
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Yuzefi Pouchy Bag ($398)

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Yuzefi Pouchy Bag
$398
from shopbop.com
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Sania D'Mina Elena Green Suede Heels ($450)

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Sania D'Mina Elena Green Suede Heels
$450
from saniadmina.com
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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.

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

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Something Navy Leopard Print Water Resistant Coated Trench Coat
$159
from shop.nordstrom.com
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POPSUGAR Essential Button Down Shirt ($33, originally $44)

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POPSUGAR Essential Button Down Shirt
$33
from kohls.com
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Citizens of Humanity Annina Trouser Jean ($238)

Citizens of Humanity Annina Trouser Jean
$238
from citizensofhumanity.com
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Dolce Vita Suvi Booties ($160)

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Dolce Vita Suvi Booties
$160
from dolcevita.com
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Marc Jacobs Snapshot Camera Bag ($295)

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Marc Jacobs Snapshot Camera Bag
$295
from shopbop.com
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The easiest way to take a miniskirt into cooler weather? With an anorak jacket and versatile sneakers.

Anthropologie Marcail Anorak ($160)

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Anthropologie Marcail Anorak
$160
from kohls.com
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Loft Plus Textured Puff Sleeve Tee ($45)

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Loft Plus Textured Puff Sleeve Tee
$45
from loft.com
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POPSUGAR Mini Skirt ($20, originally $50)

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POPSUGAR Mini Skirt
$20
from kohls.com
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Puma Carina Leather Sneakers ($65)

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Puma Carina Leather Sneakers
$65
from macys.com
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Le Specs Air Heart Sunglasses ($69)

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Le Specs Air Heart Sunglasses
$69
from lespecs.com
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Clare V Herieth Crossbody ($375)

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Clare V Herieth Crossbody
$375
from clarev.com
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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.

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

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Acne Studios Checked Wool-Blend Flannel Blazer
$385
from theoutnet.com
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POPSUGAR Belted Maxi Dress ($48, originally $64)

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POPSUGAR Belted Maxi Dress
$48
from kohls.com
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Tibi Nathan Sandals ($575)

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Tibi Nathan Sandals
$575
from tibi.com
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Mango Croc Basket Bag ($60)

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Mango Croc Basket Bag
$60
from shop.mango.com
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Jenny Bird Harley Hoops ($85)

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Jenny Bird Harley Hoops
$85
from jenny-bird.com
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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.

& Other Stories Oversized Cotton Linen Blazer ($129)

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& Other Stories Oversized Cotton Linen Blazer
$129
from stories.com
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POPSUGAR Midrise Straight-Leg Jeans ($20, originally $50)

Image Source: kohls.com
POPSUGAR Midrise Straight-Leg Jeans
$20
from kohls.com
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Converse Chuck Taylor Low Top Sneaker ($50)

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Converse Chuck Taylor Low Top Sneaker
$50
from shop.nordstrom.com
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Stella and Bow Wilcox Hoops ($65)

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Stella and Bow Wilcox Hoops
$65
from stellaandbow.com
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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.

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

Image Source: kohls.com
POPSUGAR Long Sleeve Boxy Sweater
$37
from kohls.com
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Anna Sui Asymmetric Printed Cotton and Silk-Blend Skirt ($219)

Image Source: theoutnet.com
Anna Sui Asymmetric Printed Cotton and Silk-Blend Skirt
$219
from theoutnet.com
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Adidas By Stella McCartney Adizero Adios Leopard-Bonded Mesh Trainers ($174)

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Adidas By Stella McCartney Adizero Adios Leopard-Bonded Mesh Trainers
$174
from matchesfashion.com
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Moya Jewellery Pruet Drop Earrings ($232)

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Moya Jewellery Pruet Drop Earrings
$232
from moyajewellery.com
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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.

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

Image Source: kohls.com
POPSUGAR Button-Up Midi Dress
$48
from kohls.com
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Vans Old Skool Sneakers ($60)

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Vans Old Skool Sneakers
$60
from vans.com
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Nico Giani Adenia Mini Bucket Bag ($390)

Image Source: shopbop.com
Nico Giani Adenia Mini Bucket Bag
$390
from shopbop.com
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Express Mirrored Gold Metal Frame Aviator Sunglasses ($20, originally $30)

Image Source: express.com
Express Mirrored Gold Metal Frame Aviator Sunglasses
$20
from express.com
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