Heavily associated with British Rock ‘N’ Roll legends (think The Beatles and Mick Jagger), the Chelsea boot has endured throughout the decades to become an effortlessly sleek autumn staple. This season, swap out the traditional black leather for elevated materials like colorful patent, checks, and mock croc.

BARNEYS NEW YORK Patent Leather Ankle Boots / BARNEYS NEW YORK White Patent Leather Chelsea Boots / BARNEYS NEW YORK Red Patent Leather Chelsea Boots
THOM BROWNE Checked Tweed Chelsea Boots / CHLOÉ Crocodile-Embossed Leather Chelsea Boots / DRIES VAN NOTEN Patent Leather Chelsea Boots

Fall and knee-high boots go hand and hand and this trending silhouette is a fashion favorite thanks to its outfit versatility. Pair with midi and mini skirts to amp up the proportion play or try slim jeans tucked into printed or embellished styles.

LOEFFLER RANDALL Gia Snakeskin-Stamped Leather Knee Boots
GIANVITO ROSSI Leather Knee Boots / ALBERTA FERRETTI Embellished Velvet Knee Boots / GUCCI Zumi Logo-Print Tweed Knee Boots

There’s plenty of lace-up options to work into your rotation this fall, ranging from  feminine Victorian era-inspired silhouettes to combat boots. Pointed toe ankle booties add a touch of elegance while the latter, sturdier shapes add edge.

REJINA PYO Simone Leather Lace-Up Ankle Boots / ESQUIVEL Dublin Distressed Leather Lace-Up Boots
TABITHA SIMMONS Swing Leather Ankle Boots / AMIRI Python-Stamped Leather Combat Boots / THE ROW Patty Ankle Boots

Sky-high platform boots have made a comeback as evidenced by their appearance on the FW19 runways, and for good reason. With extra height, chunky heels elongate the legs and bring a revamped, retro vibe to any look.

RICK OWENS Leather Platform Chelsea Boots / NODALETO Bulla Corta Leather Mid-Calf Boots / JIL SANDER Leather Platform Ankle Boots
R13 Leopard-Print Felt Platform Boots / GIANVITO ROSSI Dominique Leather Platform Ankle Boots / RICK OWENS Leather Platform Chelsea Boots

The Cuban heel is synonymous with Western-inspired styles and the boot shape continues to be a mainstay in designer collections from Saint Laurent to R13. Rather than a full tall cowboy boot this season, zip up a heeled bootie version that’ll go well with everything from leather pants to floral frocks.

R13 Triple-Buckle Leopard-Print Ankle Boots
PHILOSOPHY DI LORENZO SERAFINI Leather Buckle Ankle Boots / GOLDEN GOOSE Crosby Snakeskin-Stamped Leather Ankle Boots / SAINT LAURENT Lukas Leather Ankle Boots

Your toes will be happy once the temperatures fully drop thanks to this texturized assortment. Try a more sartorially minded heeled hiker from Christian Louboutin or get toasty off-duty in casual, shearling-trimmed styles by Barneys New York or Rag & Bone.

CHANEL Boot Available at Barneys New York Madison Ave Location


RAG & BONE Compass Suede & Shearling Ankle Boots / BARNEYS NEW YORK Leather & Shearling Ankle Boots / CHRISTIAN LOUBOUTIN Leather & Shearling Lace-Up Ankle Boots