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; Babton 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.
Occasion: Tailgating
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.