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 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 [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 favorite 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.
Shop Summer-to-Fall Fashion
Arthur Apparel Lady Blazer in Celery [4] ($190)
Shop Summer-to-Fall Fashion
POPSUGAR Check Tank Dress [5] ($51, originally $68)
Shop Summer-to-Fall Fashion
Susan Alexandra Lisa Bag [6] ($360)
Shop Summer-to-Fall Fashion
Lili Claspe Pearl Elizabeth Studs [7] ($100)
Shop Summer-to-Fall Fashion
Reebok Princess Classic Shoes [8] ($50)
Shop Summer-to-Fall Fashion
Carolina Lemke Wren Sunglasses [9] ($75)
Shop Summer-to-Fall Fashion
Pixie Market Olive Brown Suit Blazer [10] ($142)
Shop Summer-to-Fall Fashion
POPSUGAR Square Neck Cami [11] ($14, originally $36)
Shop Summer-to-Fall Fashion
Zara Flowy Pants [12] ($40)
Shop Summer-to-Fall Fashion
Maryam Nassir Zadeh Bruno Leather Belt in Pacific Pony [13] ($280)
Shop Summer-to-Fall Fashion
Yuzefi Pouchy Bag [14] ($398)
Shop Summer-to-Fall Fashion
Sania D'Mina Elena Green Suede Heels [15] ($450)
Shop Summer-to-Fall Fashion
Something Navy Leopard Print Water Resistant Coated Trench Coat [16] ($159)
Shop Summer-to-Fall Fashion
POPSUGAR Essential Button Down Shirt [17] ($33, originally $44)
Shop Summer-to-Fall Fashion
Citizens of Humanity Annina Trouser Jean [18] ($238)
Shop Summer-to-Fall Fashion
Dolce Vita Suvi Booties [19] ($160)
Shop Summer-to-Fall Fashion
Marc Jacobs Snapshot Camera Bag [20] ($295)
Shop Summer-to-Fall Fashion
Anthropologie Marcail Anorak [21] ($160)
Shop Summer-to-Fall Fashion
Loft Plus Textured Puff Sleeve Tee [22] ($45)
Shop Summer-to-Fall Fashion
POPSUGAR Mini Skirt [23] ($20, originally $50)
Shop Summer-to-Fall Fashion
Puma Carina Leather Sneakers [24] ($65)
Shop Summer-to-Fall Fashion
Le Specs Air Heart Sunglasses [25] ($69)
Shop Summer-to-Fall Fashion
Clare V. Herieth Crossbody [26] ($375)
Shop Summer-to-Fall Fashion
Acne Studios Checked Wool-Blend Flannel Blazer [27] ($385)
Shop Summer-to-Fall Fashion
POPSUGAR Belted Maxi Dress [28] ($48, originally $64)
Shop Summer-to-Fall Fashion
Tibi Nathan Sandals [29] ($575)
Shop Summer-to-Fall Fashion
Mango Croc Basket Bag [30] ($60)
Shop Summer-to-Fall Fashion
Jenny Bird Harley Hoops [31] ($85)
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& Other Stories Oversized Cotton Linen Blazer [32] ($129)
Shop Summer-to-Fall Fashion
Pangaia Seaweed Fiber T-Shirt [33] ($85)
Shop Summer-to-Fall Fashion
POPSUGAR Midrise Straight-Leg Jeans [34] ($20, originally $50)
Shop Summer-to-Fall Fashion
Converse Chuck Taylor Low Top Sneaker [35] ($50)
Shop Summer-to-Fall Fashion
Stella and Bow Wilcox Hoops [36] ($65)
Shop Summer-to-Fall Fashion
POPSUGAR Long Sleeve Boxy Sweater [37] ($37, originally $50)
Shop Summer-to-Fall Fashion
Anna Sui Asymmetric Printed Cotton and Silk-Blend Skirt [38] ($219)
Shop Summer-to-Fall Fashion
Adidas by Stella McCartney Adizero Adios Leopard-Bonded Mesh Trainers [39] ($174)
Shop Summer-to-Fall Fashion
Moya Jewelry Pruet Drop Earrings [40] ($232)
Shop Summer-to-Fall Fashion
POPSUGAR Button-Up Midi Dress [41] ($48, originally $64)
Shop Summer-to-Fall Fashion
Vans Old Skool Sneakers [42] ($60)
Shop Summer-to-Fall Fashion
Nico Giani Adenia Mini Bucket Bag [43] ($390)
Shop Summer-to-Fall Fashion
Express Mirrored Gold Metal Frame Aviator Sunglasses [44] ($20, originally $30)
