Summer days might still be hanging on, but the shift to cooler nights means it’s time to rethink your wardrobe. That awkward in-between season can be tricky — too hot for heavy coats, too chilly for short sleeves. The key is versatility: lightweight layers, adaptable fits, and gear that works whether you’re sweating through a late-September commute or grabbing a whiskey on a crisp October night.

This edit pulls together transitional essentials that look sharp and perform well. From breathable jackets to midweight knits, tailored pants to rugged loafers, these are pieces designed to carry you seamlessly from heatwaves to hoodie weather.

Lightweight Jackets

Lightweight jackets are the unsung heroes of transitional dressing, bridging the gap between summer heat and autumn chill. They provide just enough coverage for breezy evenings without adding unnecessary bulk, making them ideal layering pieces. From the breathable ease of linen to the durability of waxed cotton, these jackets balance style with practicality. The Flint and Tinder Linen Chore Coat, Todd Snyder Linen Harrington, and Flint and Tinder Waxed Harrington Jacket each bring their own spin on timeless design, giving you versatile options that adapt effortlessly to shifting weather.

Layering Shirts

Layering shirts are the perfect middle ground when a jacket feels too heavy but a tee doesn’t quite cut it. They add texture, depth, and versatility to your outfit while keeping you comfortable in fluctuating temperatures. Whether it’s the laid-back ease of linen, the cozy softness of brushed cotton, or the rugged character of corduroy, these shirts are built for both style and function. Options like the Bonobos Nantucket Linen Overshirt, Quince Double-Brushed Stretch Overshirt Jacket, and Reigning Champ Corduroy Campus Standard Overshirt prove that a smart overshirt can take you from crisp mornings to cooler nights without missing a beat.

Midweight Knitwear

When temperatures drop just enough to demand more than a shirt but not quite a heavy coat, midweight knitwear steps in as the perfect solution. These pieces provide warmth without bulk, giving you versatility whether you’re layering under a jacket or wearing them solo. From refined cashmere knits to rugged wool blends, they balance comfort and style with ease. The COS Cashmere Sweater, Finisterre Barents Sweater, and Quince Mongolian Cashmere Shawl Collar Cardigan each bring their own personality—whether sleek and minimalist, durable and outdoorsy, or luxe and laid-back—making them essential players in your fall rotation.

Transitional Footwear

When the seasons shift, your footwear should keep pace—light enough for lingering warm days but substantial enough to handle crisp mornings and cooler nights. Transitional footwear bridges that gap with versatile styles that look sharp in the office, out to dinner, or on a weekend getaway. The Astorflex Dartflex Loafer brings in effortless sophistication, while the Beckett Simonon Morgen Trainers offer a sleek, casual option with elevated craftsmanship. For those days that call for something sturdier, the Astorflex Brownflex Chukka Boot strikes the right balance between rugged durability and refined style, making it a go-to choice for fall layering from the ground up.

Versatile Pants

When it comes to transitional style, the right pair of pants can make or break your daily rotation. Versatile pants strike that sweet spot between comfort and polish, moving seamlessly from workdays to weekends without missing a beat. The AYR Houseplant delivers effortless drape with a relaxed fit that still feels refined, while the Faherty Movement™ 5-Pocket Pant adds performance stretch and mobility for all-day wear. For those who prefer a more structured look, the Alex Mill Standard Pleated Pant channels timeless tailoring with modern ease, ensuring your wardrobe stays adaptable no matter the season.

Light Outerwear Accessories

Accessories are often the unsung heroes of transitional style, offering functional layering without the bulk of outerwear. As the seasons shift, a premium suede cap adds polish while shielding from unexpected sun or drizzle, while a tote like Herschel’s Heritage ensures your essentials move with you in effortless style. For those brisk mornings or cool evenings, a lightweight linen scarf, such as John Henric’s geometric design, provides just the right touch of warmth and refinement. Together, these accessories elevate even the simplest fits, keeping you adaptable and sharp when the weather can’t make up its mind.

Transitional style doesn’t have to mean compromise. With pieces like these — breathable jackets, midweight knits, versatile pants, and sharp accessories — you’re set for whatever the season throws your way. From hot afternoons to cool nights, this edit keeps you moving in comfort and style.