How to Transition Your Wardrobe From Summer to Autumn With Ease

Autumn is an incredible time of year for fashion, but it can also be a frustrating one. In many parts of the country, it may be cool in the morning, but by the afternoon, the sun is shining and you find yourself needing to shed a layer of outerwear. The summer-to-fall transition can be tough, wardrobe-wise, but don’t worry—we’ve got you covered.
In order to help you dress for the fluctuating weather that is the fall season, SI Swimsuit’s fashion editor Margot Zamet and assistant editor Liz Wentworth have put together the ultimate shoppable edit for transitional dressing between summer and fall. It’s all about layers, seasonal hues and textures, and below, you’ll find three curated looks that feature plenty of sweaters, jackets, cool accessories and some seriously great fall footwear.
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Elevated basics
A crisp white tee worn under a cozy zip-up mock-neck sweater is perfect for the season, while shiny black loafers are super trendy. Denim and all black accessories round out the look.

- The Baby Tee, $54 (coucouintimates.com)
- Rounded Wool Mock-Neck Zip-Up Jacket, $229 (cos.com)
- The Aela Sunglasses, $148 (jimmyfairly.com)
- Large Leather Tote, $495 (maisonessentiele.com)
- Rowan Flare Outland Jeans, $365 (ebdenim.com)
- Schutz Tyche Loafer, $198 (revolve.com)
Upscale elegance
A white cashmere top is a wardrobe staple, and we adore these drawstring wide-leg jeans for the fall season. Plus, when the temperatures dip, this belted jacket will really tie your look together.

- The Frankie Shop Kelia Belted Padded Jacket, $329 (mytheresa.com)
- Rag & Bone Featherweight Phoebe Drawstring Wide-Leg Jeans, $288 (saksfifthavenue.com)
- High Collar Ultralight with Cashmere Top, $65 (intimissimi.com)
- Flattered Clay Clutch, $375 (revolve.com)
- AIRE Equator Sunglasses, $49 (revolve.com)
- Margot Choc Crinkle Boot, $250 (tonybianco.com)
Casual and sporty
Whether you’re running errands or heading to the weekend farmers market, this outfit is a low-effort way of looking put together. While the jacket is a great layering piece for fall, the bandana-print tote brings a fun energy to this outfit.

- The Raglan Tee, $68 (coucouintimates.com)
- Painter Jean, $168 (jcrew.com)
- Gora Signature Logo Brighton Jacket, $310 (sportyandrich.com)
- Original Wayfarer Classic, $244 (ray-ban.com)
- Call It By Your Name Maxi Cabas Quilted Bandana-Print Cotton Tote, $405 (net-a-porter.com)
- Dream Ballerina Flat, $445 (mansurgavriel.com)
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Cara O’Bleness is a writer and editor on the Lifestyle and Trending News team for SI Swimsuit. Prior to joining SI Swimsuit in 2022, she worked as a writer and editor across a number of content verticals, including food, lifestyle, health and wellness, and small business and entrepreneurship. In her free time, O’Bleness loves reading, spending time with her family and making her way through Michigan’s many microbreweries. She is a graduate of Michigan State University’s School of Journalism.