With the changing of the leaves comes a whole host of cozy activities just as picture-perfect. So get in the frame, and dress accordingly.
Occasion: Girls' Brunch
Why It Works: This elevated play on loungewear will get you noticed but still out the door in 10 minutes. The upgrades: Layer an oxford shirt under a quilted sweatshirt for preppy polish, and skip sneakers in favor of brogues to sharpen casual knit pants. Oversize shades and a baseball cap mean minimal hair and makeup time (and more sleep!).
Shop It: Gentsco cap, $99, gentsco.com; Babaton for Aritzia shirt, $85, aritzia.com; Trademark pullover, $298, trade-mark.com; Club Monaco coat, $695, clubmonaco.com; Massimo Dutti pants, $110, massimodutti.com; Kara, $480, karastore.com; Sermoneta Gloves, $150, at Sermoneta Gloves, 212-319-5946; DKNY sunglasses, $90, at Sunglass Hut, 212-759-3720; Tommy Hilfiger shoes, $79, tommy.com.
Prepare for the big game in colorful layers so you'll be toasty and scoring plenty of style points. (Stick to face paint in the same color scheme.)
Why It Works: Everything about this bright blue quilted jacket says, "Go team!" Keep the sporty spirit popping with a varsity-like striped scarf, but in a sophisticated palette like ocher and gray. Bonus: It can double as a shawl.
Shop It: Saturdays NYC cap, $40, saturdaysnyc.com; Ann Taylor sweater, $98, anntaylor.com; Equipment shirt, $228, equipmentfr.com; J.Crew bomber jacket, $275, jcrew.com; Donni Charm scarf, $219, donnicharm.com; DL1961 Premium Denim, $178, dl1961.com; Cole Haan oxfords, $268, colehaan.com.
Why It Works: Love sports but don't do parking-lot couture? A crewneck and miniskirt combo is cute but laid- back when tempered with high-tops. Sneak in an extra print (and make new friends) courtesy of a rolled-up blanket.
Shop It: Warby Parker sunglasses, $95, warbyparker.com; Verloop touch-screen gloves, $65, verloopknits.com; CluToo layered top, $127, shopbop.com; J Brand jacket, $620, nordstrom.com for stores; Lacoste skirt, $250, lacoste.com; Time's Arrow handbag, $395, bergdorfgoodman.com for stores; Pendleton Woolen Mills blanket ($239) and sling ($25); pendleton-usa.com; Adidas Originals sneakers, $75, adidas.com.
Occasion: Holiday Dinner
Match your outfit to the menu: Nothing says Thanksgiving like a rich assortment of fall hues, such as warm squash and deep wine.
Why It Works: For a more formal gathering, fluid silhouettes—like this season's robe coat over a silky blouse and a midiskirt—offer easy elegance (and room for seconds). A structured tote and pointy-toe pumps amp up the polish.
Shop It: Mango coat, $230, mango.com; By Malene Birger blouse, $385, at Edit by LBP, 225-757-5909; Shinola wrap watch, $525, at Shinola, 917-728-3000; Karen Millen bag, $380, karenmillen.com; Raoul skirt, $255, raoul.com; ASOS pumps, $72, asos.com.
Why It Works: Let slouchy trousers in graphic black-and-white do the talking and keep the rest of the outfit simple. Add some tonal warmth with a burgundy sweater, then relax about spilling any of that merlot.
Shop It: Everlane shirt, $78, everlane.com; AYR sweater, $125, ayr.com; 1. State coat, $288, lordandtaylor.com; Caravelle New York wrap watch, $75, jcpenney.com; Apiece Apart trousers, $385, apieceapart.com; Tory Burch tote, $385, toryburch.com; Ivanka Trump flats, $130, bloomingdales.com for stores.
Occasion: Apple Picking
Why It Works: Want your pick of the bunch? Durable denim was made for climbing, and yellow galoshes will let them know you mean business. Bring a charming wicker tote to hold your spoils—all the better if it matches your topper.
Shop It: Cuyana infinity scarf, $65, cuyana.com; Vince coat, $795, vince.com; Ace & Jig sweatshirt, $298, aceandjig.com; Wildfox sunglasses, $179, wildfox.com; Buji Baja gloves, $74, hatattack.com; Crippen jeans, $265, intermixonline.com; Basketville tote, $25, basketville.com; Hunter boots, $138, hunterboots.com.
Why It Works: A long skirt coupled with ankle boots will (stylishly) protect your legs while you're strolling in the grass. Go heavy on the knits—a chunky cardi over a thick sweater never fails—in case you decide to stay for a hayride at dusk.
Shop It: White + Warren scarf, $298, whiteandwarren.com; Elizabeth and James cardigan, $395, at Flaunt Boutique, 925-831-9923; Nanette Lepore pullover, $298, nanettelepore.com; Bulova wrap watch, $185, jcpenney.com; Warehouse skirt, $63, warehouse.andotherbrands.com; French Connection bag, $78, zappos.com; Dolce Vita ankle boots, $169, dolcevita.com.
Occasion: Date Night
Why It Works: Give a nuzzle-worthy turtleneck and kicky ombré jacket some edge with provocative leather. A tasseled cross-body and suede Chelsea boots lend a cheeky touch—perfect for catching that fright-night blockbuster.
Shop It: COS jacket, $225, cosstores.com; Uniqlo turtleneck, $80, uniqlo.com; Bebe cuff, $34, bebe.com; MiH leather skirt, $485, mih-jeans.com; the Common Knowledge bag, $480, thecommonknowledge.com; Pretty Ballerinas boots, $369, prettyballerinas.com.
Why It Works: Cider cocktails on the agenda? Dare to be sleeveless with a little help from a tailored white coat. Drape it over the back of your chair to reveal a girlie LBD, updated in a fiercely feminine floral brocade.
Shop It: Rebecca Taylor dress, $495, saks.com; Pink Tartan coat, $795, nordstrom.com; Henri Bendel wallet, $228, henribendel.com; A.V. Max bracelets, $35, avmaxaccessories.com; Loft pumps, $90, loft.com.