A trim little tweed jacket with perfectly placed pockets. If you’ve only seen that, you’d be forgiven for thinking of its designer, Marissa Webb, as an ultra-ladylike type (just add a strand of pearls!). The truth? Webb’s a tomboy to the core, and though she can sport classic tweed with the best of ‘em, she wears it her way: with ripped denim, a graphic tee, and those Isabel Marant boots we’ve been coveting for months.

She’s an advocate of personal style above all, which means she wants you to wear her collection however you’d like (with a tutu and a top hat? In the spirit of the inimitable Diana Vreeland, why not?). But if you’re in search for a bit of outfit inspiration, look no further than Webb herself; her wildly chic and ultimately unique style has us wanting to copy it down to the very last piece of generously-stacked jewelry.

We challenged Webb to put together five perfect fall looks: for a day of shopping, a night on the town, a lunch date, a cocktail affair, and an evening of entertaining at home. With the holiday season fast approaching—and our need for outstanding ensembles becoming ever-pressing—let’s just say we’ll be taking plenty of cues from Ms. Webb’s picks. Shorts for a cocktail party? Why not?


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Makeup by Barneys New York resident makeup artist Jason Ascher; call 212.833.2782 for appointments. Hair by Idan Chen at B3 Barneys Blow Bar by Valery Joseph; call 212.833.2600 for appointments. Photography by Christopher Talbot.