Piecing together a come-hither look, especially when you factor in fickle fall weather (think: Indian summer warmth one day, brisk fall temps, the next) can be a bit tricky. But we’ve got you. Whether you’re doing the traditional fall bucket list activity (ahem, a trip out to the apple orchard) or have something a little bit more romantic up your sleeve, we’ve got four stellar date night-approved outfit ideas that are guaranteed to make a lasting impression.

Pumpkin Picking

Autumn days are here, and we’re delivering up the optimal fall uniform for a date at the pumpkin patch. Avoid appearing PSL-level basic by opting for a frilly goldenrod knit sweater with a trend-right corduroy button-front mini and these retro-chic gingham slingbacks. Transition your look from day to night with a set of extraterrestrial-inspired studs and a streamlined leather heritage satchel that slays all day.

Clockwise from top left: Demlylee x Clare V. Nora Sweater ($325), Catbird Tiny Dancer Single Stud Yellow Gold ($48), The Cambridge Satchel Company Conductors Bag in Patent Leather ($235), Margaux The Slingback ($195), Wilfred Free Karmen Skirt ($85)


Is there anything more “Aww!”-worthy than catching a meteor shower while cuddling up to your boo? Enter the celestial-inspired getup that will have you seeing stars for days. Toss this swishy metallic pleat skirt from Scotch & Soda on alongside a ribbed crop top and an off-duty military topper for after-hours appeal. Add in extra AF accessories — evil eye clutch and cha-cha-ready tassel earrings, we see you — and M.Gemi’s cult favorite Corsa boots. The sensible block heel will ensure a blister-free rendezvous.

Clockwise from top left: Mango Patched Contrasted Cuffs Parka ($130), & Other Stories Ribbed Off-Shoulder Top ($39), Vanessa Mooney The Dynasty Earrings ($45), Poppy Lissiman Classic Black Evil Eye Clutch ($110), M.Gemi The Corsa ($348), Scotch & Soda Pleated Skirt ($125)

Fall Tailgate

Two, four, six, eight, who’s ready to tailgate? With a throw-on-and-go long-sleeved maroon shift dress and a trusty denim jacket on standby, you’ll be equipped for nippy temps. Peep this autumnal striped leather crossbody bag from Clare V. that’s ready to tote just the essentials. No fake enthusiasm for sports here, and we’ve got the rah-rah-worthy pin from Ban.do to prove it. Complete your post-collegiate lewk with an olive pom-pom-strewn cap and sensible white kicks.

Clockwise from top left: H&M Pile-Lined Denim Jacket ($70), Ban.do Enamel I Like Sports Pin ($10), Zara Pom-Poms Cap ($20), Mango Sleeve Detail Dress ($40), Veja Esplar Sneaker ($120), Clare V Midi Sac Georgia Midi Stripe ($325)


Picture this: you, your date, and a shared bottle of vino (or mulled cider) as you engage in conversation at the vineyard. You may just want this cult-favorite, tissue-thin layering turtleneck from J.Crew in every color. For a hit of femme, slip this sartorial workhorse on alongside a floral embroidered lace skirt and architectural hoops. In the accessories department, aim for sophisticated add-ons, namely a structured black box bag and a pair of these Eugenia Kim blush slides accented with a giant ol’ pom. Offset your look with a bold red lipstick that speaks to your inner vixen. Et voilà!

Clockwise from top left: J.Crew Tissue Turtleneck T-Shirt ($30), Tictail Night Out Gold Keyhole Hoops ($60), Bobbi Brown Luxe Lip Color in Parisian Red ($35), Mango Coffer Bag ($70), Eugenia Kim Poppy Flat ($465), French Connection Mazie Floral Mini Skirt ($228)

Which of these fall date night-approved getups will you be rocking? Follow us on Pinterest for more style inspo!

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