Many of us revel at the change of seasons. The month of September serves as a swan song to the summer past. The gorgeous, changing color of the leaves have historically served as a beacon for tourists, as well as photographic notations of what makes New England different from anywhere else in the world. With the arrival of Autumn in New England comes a necessary wardrobe rotation. 


From headgear to footwear and everything in between, what New Englander’s wear during the cooler months sits in stark contrast to that worn during more humid, summer months. We store our sandals, flip-flops, and whites, and replace them with boots, booties, and a stash of earth tones, nudes, and neutrals. We say farewell to tank tops and shorts, and hello to denim, corduroy, and heavier fabrics such as wool.

This year, leading stylists have suggested that hardware-heavy boots with buckles are trending for pairings with jeans, leggings, tweeds, sweater, puffer skirts, and Burberry jackets. Keeping those insights in mind, here are a few inspirational, ‘boo-tiful’ looks to ‘kick off’ boot (and bootie) season:

Over-the- Knee Boot

Classic meets comfort in Charleston Shoe’s over-the-knee SoHo boot. Designed with a signature stretch back for easy slip-on style and fit.

Charleston Shoe SOHO Over The Knee Boot

 Ankle Boot

With a stacked two-inch heel and squared toe, this zip up bootie from Charleston Shoe in either black or navy blue leather, adds stylish versatility to your footwear wardrobe.

Charleston Shoe DRAKE Ankle Boot
Knee High Boot

Sam Edelman’s knee-high Elsy boot bridges the gap between aspiration and attainability. The leather upper is adorned by a delicate gold buckle.

Sam Edelman Knee High Elsy Boot

Bootie Sneaker

Cocktail Sneakers’ best-selling bootie sneaker, the Outsider is a luxurious calfskin leather ankle-boot sneaker featuring dressy crisscrossed silver, metallic piping. Available in black, slate blue grey and blush, the Outsider also features this season’s favorite enhancement: a buckle!


Autumn wouldn’t be complete without boots. Whether your preference is above the knee, at the knee, or well below the knee at ankle height, boots (or booties) pair well with the layered looks of the season.