What to Wear Where

Whether you're headed out for a pumpkin spice latte, off to a tailgate, or being responsible and, y'know, going to work, here's how to get it right every time this fall.

- Hannah Dorough

In-Person Office Days

Last season's strong-shoulder suits were an overcorrect. Go for flowy, wide-leg pants, a silk top, and a turtleneck underlayer that's always a classic. Tie? Optional!

Kurtis Stripe-Print Shirt, $395; us.sandro-paris.com LongSleeved Woolen Turtleneck Top, $69, and Wide-Leg High-Waist Pleated Trousers, $139; stories.com Brown Print Tie, $35; toddsnyder.com Lucy Earring Set, $72; baublebar .com Gold-Plated Dome Ring, $39; cos.com

A Meetup in the City

For a museum or matinee, combine a trim blazer with a full skirt and a graphic sweater (the preppier the better!) for a look that's smart but fun. Bonus points for power-clashing plaids.

Prince of Wales Jacket, $498, Merino Cashmere Scottie Sweater, $248, and Taffeta Black Watch Skirt, $298; brooksbrothers.com Brown Leather Belt, $59; shop.mango .com Agathea Chunky Loafer, $268; thereformation.com Lucy Earring Set, $72, and Sophie 18K Gold Necklace, $88; baublebar.com

A Dressy Dinner Out