Back to Basics

When it comes to thinking about pre-fall fashion, we were inspired by the girl-meets-boy aesthetic of a young Diane Keaton in the iconic movie Annie Hall-an image for which Gap's new denim styles provided the perfect base. Using their Long & Lean, Always Skinny, and Easy Straight cuts, we updated Keaton's much-emulated look by opting for contrasting textures, shrunken jackets, and a few well-placed accessories. These of-the-moment ensembles offer the ideal blend of vintage flair and au courant fashion, and are infused with the perfect amount of androgynous style. The resulting outfits reflect not only a highly-wearable approach to what was seen on the F/W 10 runways, but are also intriguing sartorial combinations that are sure to springboard you straight into the next season.-Liza Kaplan

Photographer: Justin Coit; Creative Director: Katherine Power; Producer: Liza Kaplan; Style Director: Laurie Trott; Assistant Stylist: Nikki Tavdi; Hair: Jen Atkin, The Wall Group; Makeup: Erin Smith, Celestine; Nail Technician: Barbara Warner; Model: Sarah Joffs, LA Models.

Shop The Spreads

Look 1:
Gap Easy Straight Destructed Jeans ($69.50), Topshop Wool Flat Top Hat ($44), Swedish Hasbeens Lace Up Boots ($335) in Nature, Watch, stylist's own, Suspenders, stylist's own, H&M Bracelet ($4.95), Levac Bowtie Shirt ($160, 718.797.3776).

Look 2:
Gap Always Skinny Jeans ($69.50), Steven Alan Murielle Bow Neck Top ($188), Vintage hat ($195) from The Way We Wore, American Apparel Unisex Knit Long Grid Vest ($68) in Navy + Medium Beige Grid, Iro Grace Jacket ($335, 718.797.3774), Giles and Brother Multi Chain Bracelet ($125).

Look 3:
Gap Easy Straight Destructed Jeans ($69.50), Swedish Hasbeens High Heeled Jodhpur ($335) in Plum, American Apparel Unisex Textured Italian Short Sleeve Button-Up Shirt ($54) in Dark Charcoal, Opening Ceremony Black Specked Wool Tie ($95), Vince Draped Cashmere Vest ($225), Vintage Cartier scarf ($225) from The Way We Wore, Vintage purse ($195) from The Way We Wore, Cooperative Felt Boater ($34), Myne Bracelet ($405, 310.275.1930).

Look 4:
Close up of Look 2.

Look 5:
Gap Long & Lean Jeans ($59.50), Suspenders, stylist's own, A.P.C. Beige Chevron Blazer ($500, 212.966.0069), Vintage handkerchief ($65) from The Way We Wore, Band of Outsiders Sleeveless Button-Down Shirt ($250), Justin Chestnut Marbled Deerlite Roper Boots ($69.99), Oliver Peoples Linus Cloisonne Glasses ($365, 310.633.1891), Vintage hat ($195) from The Way We Wore.