Tip: Don't give up your leather jackets come winter. It's all about smart layering—a turtleneck, a sleeved dress, and a roomy leather jacket is a cool-weather version of the standard Model-Off-Duty look. Switch out those platform sandals for a pair of platform boots.
Above, clockwise from left: Street style photo by Craig Arend/Altamira; ASOS Double Wrap Waist Belt, $20.22, available at ASOS; Le Sentier Button Front Leather Jacket, $475, available at FarFetch; ASOS Dahlia Floral Dress, $97.73, available at ASOS; Steve Madden Mariell Boots, $189.95, available at Steve Madden; MZ Wallace Black Bedford Purse, $345, available at Refinery29 Boutiques.
Tip: Wear shorts right through to winter, just remember to layer a thick pair of black tights underneath and top them off with some warm layers.
Above, clockwise from left: Gala Gonzalez style photo from Amlul; MAJE Arletta Wool Coat, $620, available at Net-a-Porter; Character Hero Plaid Wool Shorts, $58, available at Urban Outfitters; BC Shoe Shockwave Oxfords, $42, available at Endless; J. Crew Cambridge Cable Crewneck Sweater, $74, available at J. Crew; Warehouse Leather Buckle Detail Satchel, $84.25, available at ASOS.
Tip: A graphic sweater and slim-fit jeans is a classic duo. Come winter, counter the boxy fit of the sweater with a tailored cape in a sleek silhouette.
Above, from left: Street style photo by Mr. Newton; Karen Millen Soft Draped Jacket, $475, available at Karen Millen; Motel Dot Sweater, $70, available at Topshop; Raven Remy Skinny Jean, $173, available at Revolve; Modcloth Braided Belt, $14.99, available at ModCloth; Bettye Muller Suede Bootie, $250, available at Neiman Marcus.
Tip: Swap out your staple cardigans for an elegant drape-front jacket.
Above, from left: Street style photo by Claire Thomas; Hayden Harnett Michi Tank, $94, available at Hayden Harnett; Catherine Malandrino Textured Wool-Blend Coat, $495, available at Net-A-Porter; Blank Acidic Knit Denim Skirt, $68, available at DJPremium; Loeffler Randall Joanna Oxford, $375, available at Barneys New York.
Tip: Opt for a colored pair of hosiery that adds some pizazz to an otherwise neutral palette.
Above, from left: Street style photo by Mr. Newton; Madewell Ice Cluster Bib Necklace, $118, available at Madewell; Vince Waxed Cotton Utility Jackt, $595, available at Net-a-Porter; Maurie and Eve Leopard Heel, $275, available at Revolve Clothing; We Love Colors Tights, $12.50, available at We Love Colors; Haute Hippie T-Shirt Dress, $98, available Nordstrom. .
Tip: We're loving this Annie Hall look. To winterize the look, add a pair of thick ribbed tights and cherry-red boots for an unexpected surprise to the classic '70s outfit.
Above, from left: Street style photo by Mr. Newton; J. Crew Harris Tweed Blazer, $595, available at J. Crew; Stetson Wool Fedora, $78, available at Madewell; American Apparel Chiffon Full Skirt, $58, available at American Apparel; Swedish Hasbeen Red Boots, 377, available at Coggles; Topshop Pointelle Footless Tights, $24, available at Topshop.