20 Must-Have Items To Transition From Summer To Fall

With these transitional pieces, you’ll look great no matter the weather this autumn.

August 30, 2023 by The IMBOLDN Editors

20 Must-Have Items To Transition From Summer To Fall

With these transitional pieces, you’ll look great no matter the weather this autumn.

August 30, 2023 by The IMBOLDN Editors

While we love the crisp fall temperature that begins to creep in around this time of year, we admit that dressing for this weather can be a challenge. During these seasonal shifts, it’s imperative to have light layers, sensible shoes, and items that can go from work to weekend seamlessly. Scroll down to see the pieces out editors are snagging before the season changes.

Everlane The Relaxed Linen Short-Sleeve Shirt

Pair this shirt with your favorite jeans for the ultimate relaxed look. Perfect for those warm early fall days when it’s too early for long sleeves or heavier fabrics.

$78

Relwen Flyweight Flex Blazer

This casual sport blazer offers Relwen’s signature heritage aesthetic and is perfect to throw on over a tee on chilly mornings and cool evenings.

$298

Everlane The Filled Canvas Jacket

Create a polished look with this tough, triple-stitched canvas jacket. A 9.3 oz cotton canvas exterior handles the world outside, while 100% recycled, 60g PrimaLoft insulation keeps the warmth inside.

$168

Wills Garment Dyed Blazer

Pair this sleek blazer with a polo, a button-down, or even a tee for a casual-but-put-together look that’ll have you feeling like James Bond on his day off.

$228

Everlane The Bomber Jacket

This Everlane jacket offers a new take on the MA-1 flight jacket style and is perfect for fall weekends. It’s made of a recycled, water-resistant cotton–polyester blend and complete with magnetic closure pockets and a two-way zipper.

$148

Astorflex Bitflex Chelsea Boot

Handmade in Northern Italy, these slip-on boots are eco-friendly, as comfortable as walking on a cloud, and elevate any casual outfit.

$215

Relwen Nautical Neats Shirt

This timeless buttondown is made from a soft and durable cotton for a refined look that will take you everywhere from checking out the newest restaurant in town to after-hours work parties and everywhere in-between.

$178$97

Astorflex Dartflex Loafer

With a comfy leather build that conforms to your foot whether you wear them with socks or not, these Italian-made loafers are a silver bullet for easygoing, effortless style.

$225

Buck Mason Field-Spec Rugby Crew

This relaxed, long-sleeved, heavyweight cotton tee is modeled after a vintage rugby shirt. It’s a solid, substantial stand-alone tee for cooler weather and works perfectly under a blazer or chore coat.

$88

Everlane The Brushed Flannel Shirt

This Everlane flannel shirt is warm, durable, and made for supreme comfort. Throw it on over a tee or wear it under a heavier jacket on chilly evenings.

$90

Flint and Tinder Bedford Cord Waxed Barn Jacket

This Bedford Cord Waxed Barn Jacket is a genuine workhorse of a jacket that’s packed with all the utilitarian functionality you’d expect from a longstanding staple of American workwear. Wear it over a tee or light sweater during fall days.

$228$114

Everlane The No-Sweat Ribbed Crew

Made from a blend of OCS-certified organic cotton and no-sweat recycled COOLMAX® EcoMade polyester that wicks away moisture from your skin, this sweater is a relaxed take on our classic cotton sweater, with the ribbed stitch adding a textural edge.

$98

Everlane The Canvas Barn Jacket

Get work done—and look good doing it in this organic canvas cotton jacket that features a corduroy collar, patch pockets with flaps, and traditional patch detailing at shoulders and elbows.

$175

Buck Mason Avalon Knit Polo

This classic fit sweater polo in yarn-dyed 16 gauge cotton jersey features a three-button closure and rib finishing at the cuffs and hem. It’s made with hand-linked seams for improved durability and comes in a variety of perfect fall neutrals.

$118

Wills Wrinkle Free Chore Coat

Built from a wrinkle-free linen fabric that travels exceptionally well, this laidback chore coat will look just as good being pulled out of your bag as it did going in.

$198$158

Flint and Tinder Donegal Architect Shirt

Crafted from a premium Donegal fabric with a soft feel and textured look, this shirt is reminiscent of a classic Oxford, but has reinforced elbow patches, a split back yoke, and a side vent gusset that’s commonplace in hardwearing workwear pieces.

$138

Faherty Brand Inlet Knit Blazer

Made from sustainable organic cotton and recycled polyester, this lightweight blazer is soft, stretchy, and sports a handsome tailored fit.

$198

Flint and Tinder Bone Button Western Shirt

This classic, durable Bone Button Western is the perfect shirt for fall days when you want to look rugged and polished at the same time.

$158

Le Mont St Michel French Moleskin Work Jacket

Built from a heavy moleskin cotton and constructed with hardwearing craftsmanship, this jacket is a transitional layer you’ll have—and wear—for decades to come.

$275

Buck Mason Dyed Cotton Traveler Sweater

This slim fit crewneck sweater from Buck Mason features ribbing at the cuffs, neck, and hem. It’s constructed with hand-linked seams for durability and garment dyed and washed for a lived-in look and feel.

$138

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