5 Transitional Pieces to Take You from Summer to Fall

Labor Day has come and gone, which means summer is on its way out. Arguably the best time period for spending time outside, the transition from summer to fall also brings on plenty of wardrobe opportunities.

It may not be time for fur-lined boots and pea coats just yet, but you can still sneak in a couple of boot styles and even continue wearing some of your favorite summer shoes as the leaves start falling. We’re sharing five effortless transitional styles and how to style them during the in-between period.

DONOVAN BEIGE WINGTIP CHELSEA BOOTS

Meet the reinvented Chelsea boot. The lighter suede upper makes the shoe more adaptable to both seasons, while the brogue detailing and pop of red make it stand out.

What to wear: Cool and casual days call for jeans and a tan tweed blazer on top of a white button-up (top button open, fellas). Hotter days, on the other hand, need nothing more than this pair with black denim and a relaxed gray tee.

LOGAN NAVY CHUKKA BOOTS

A boot disguised as a sneaker, you can wear Logan with a range of colors and styles because of his versatile color palette. If there’s any style to add to your collection this season, it’s this one — you just can’t go wrong with styling.

What to wear: While hot weather prevails, wear Logan with light-wash denim and a relaxed striped tee. Then, when shorter, cooler days set in, you can pair him with navy chinos and a gray cowl neck sweater.

BRICK-AND-MORTAR COGNAC SNEAKERS

It’s mixed medium for mixed moods with Brick-and-Mortar as we transition into fall. This pair combines slate gray sheepskin suede and cognac calfskin leather for a style that you can wear through summer shenanigans and into fall festivals.

What to wear: Still braving the heat? We recommend some navy shorts and a printed short-sleeve button-up that carries a pop of navy to maintain a coordinated look. When the cold front makes itself known, grab your favorite pair of jeans and pull on a gray sweater.

BOARDWALK BLACK HORSE-BIT SNEAKERS

Laid-back, airy but still dark enough for fall, Boardwalk matches both seasons. This The Chancellor Collection shoe gets a chic upgrade from leather-wrapped silver horse-bits, making it cool enough for an amphitheater concert and sporty enough for a classy game-day getup. 

What to wear: While you’re still riding the heatwave, pick up a pair of white shorts and a blue short-sleeve button-up. For fall flair, follow Kam Chancellor’s lead and don a gray pinstripe suit.

JAKE BLACK CAP-TOE LACE UPS

When you need to dress it up for work, Jake in black is your new transitional go-to. While black can come off as a more serious color, we designed this style with brown shades and a classic silhouette for a boost in versatility.

What to wear: For work, go for grays — gray dress pants and a white button-up, for example. If it’s cooler, layer on a gray sweater or cardigan. For a more casual, warm-weather look, wear jeans and flannel. Done.