Right up there with pumpkin spice lattes and festive pinecone arrangements at the grocery story, a true harbinger of fall is staring down two months’ worth of outdoorsy plans with nothing interesting to wear. That whole slouchy flannel, cable knit, boyfriend jeans thing? You’ve been there, done that, and are so ready to move on.
Allow us to help you with the five foolproof outfit ideas below, each tailored to a different autumn activity—and, naturally, priming it for an Instagram opportunity (hey, we all do it!). Now on to the next challenge: finally deciding on a look to wear this Halloween (both this and this can help with that).
1. FOLIAGE-APPRECIATION HIKE
Two things that instantly guarantee an enjoyable walk through the woods: a beautiful array of golden and red leaves, and leggings you don't mind being photographed in (who knows what kind of snaps the people behind you are taking?). Work in a few easy-to-remove layers—a light hoodie and quilted vest combination can’t go wrong—because while the air may be cold, you’re likely to work up a sweat.
Shop the look: A.P.C. X Outdoor Voices sweatshirt, $101; matchesfashion.com. Uniqlo vest, $50; uniqlo.com. COS hat, $49; cosstores.com. Lucas Hugh leggings, $280; net-a-porter.com. Nike shoe, $90; nike.com.
2. PUMPKIN PERUSING
And, yes, eventually pumpkin picking, but isn’t half the fun inspecting each gourd three times over to find the roundest, smoothest, and orange-iest one? Keep cozy the whole time in an oversize sweater, joggers, and slide-on mules—an ensemble that goes straight to the hot cocoa run you’ll make between leaving the farm stand and making a jack-o'-lantern at home.
Shop the look: Tibi sweater, $395; tibi.com. Jules Smith earrings, $19 (originally $30); barneyswarehouse.com. BaubleBar necklace, $38; baublebar.com. Majestic sweatpants, $145; stylebop.com. Kristin Cavallari mule, $120; nordstrom.com.
3. APPLE PICKING
Simple, utilitarian silhouettes may be a no-brainer for an afternoon in the orchard, but you also want the mix to feel special. The perfect balance? A less expected workwear combination—like a boilersuit and field jacket rather than your standard button-down and jeans—paired with more refined accessories, such as pointy-toe loafers and a drawstring backpack.
4. WINE TASTING
Oh, hey there, fancy lady with your discerning palate for dry Chardonnays and full-bodied Bordeaux. No? You are not a committed vino aficionado? Fake it anyway at your next tasting with an elegant sequined cami, black skirt, and sleek pointy-toe pumps (and try not to mention you keep the boxed stuff at home).
Climbing into the back of the tractor, sitting on straw bales, crunching across a field to get back to your car—these are plans that clearly call for jeans. As for the rest of your look? Keep it casual but cool with the help of a matching jean jacket (a coordinating wash feels very "right now"), graphic sweater, and streamlined sneakers (if you're worried about mud and dust ruining pure white, an all-black designer works just as well).
Shop the look: Zara sweater, $26; zara.com. J.Crew denim jacket, $128; j.crew.com. AG Adriano Goldschmied jeans, $319; stylebop.com. Kara crossbody, $475; barneys.com. Common Projects sneakers, $450; net-a-porter.com.