Summer is endlessly glorious and magical, but toward the end of August, there’s a hint of fall floating in the breeze—a signal that it’s almost time to box up the breezy sundresses and sandals and break out the plaids, cashmere sweaters, and boots. All I want to do is layer up and get cozy.

As a kid, I was obsessed with going back-to-school shopping. I would plan out my picks for weeks, marking pages in my Seventeen and YM magazines for inspiration before hitting the mall. These days, I still get the urge to revamp my entire wardrobe for the autumn, but when I get down to it, I rely on a handful of closet workhorses to fulfill my sartorial dreams.

Sure, it sounds cliché to say black pants and a turtleneck are fall essentials, but it’s not about the pieces themselves—it’s about the magic you can make with them! Any good wardrobe is built upon a handful of hardworking, versatile pieces like my go-tos; I can throw on a fully sequined jacket from the thrift store, a hot pink faux fur collar, or a shoulder-grazing pair of cobalt blue earrings and go. They allow me to get creative when I’m in a fun mood or keep things simple when I need to get out the door fast. They’re tried and true old friends who never let me down and always make me feel good—the cornerstones of my fall looks both dressed up and dressed down.

01

Ankle-length cashmere or wool coat.

Any color will do, but I prefer a camel shade for the autumnal months. Throwing this over anything, even stretched-out sweats, makes it feel like an outfit and not just what I’m wearing to walk the dog. A camel coat is so versatile and can go literally anywhere, from a gas station in the middle of nowhere to a fancy wedding party. It’s also infinitely customizable according to your signature style; I like to pin vintage fur pieces to the collar to change things up, or add a few sparkly brooches to the lapel. It can be very Ralph Lauren with a high-necked plaid blouse and trousers or downtown cool with skinny black pants, a turtleneck, and a kitten heel. These are easy to find at vintage and secondhand stores, so don’t feel like you need to drop a ton of cash on a fall coat unless you really want to.

02

Loafers.

You name them, I’ve got them. Croc print vintage Ralph Lauren? Check. Classic Bass Weejuns? Yep. Platform ‘90s-inspired? Uh-huh. Loafers are the ultimate fall shoe, especially when you’re not entirely ready to transition back to socks and boots. Plus, they go with literally everything and work for any personal style vibe—and they’re always at the thrift store.

03

Eileen Fisher stretch crepe black skinny pants.

These are the best pants on earth, quote me. I have them in a bunch of colors but black is always my go-to. They never lose their shape, they pack up like a dream, and they’re so flattering and comfortable—they hug your body but aren’t skintight. The pants are part of Eileen’s “System” of pieces meant to wear forever and match with everything you own, and I reach for mine at least twice a week in the fall and winter. Move away from the idea that Eileen Fisher is for older ladies. Eileen is for people with taste. I would never steer you wrong on something so important!

04

A slouchy beanie.

Back in 2006, I was obsessed with the “indie girl” beret look (think Kirsten Dunst in Elizabethtown) and I still love it today, though I tend to wear my hats on my forehead and not pushed back on the crown as in Urban Outfitters days of yore. My favorite is a fuzzy alpaca beret, but I love a classic wool or felt beret too. It covers up a bad hair day, adds a little oomph to a bland ensemble, and keeps your head warm on those unexpectedly chilly mornings.

05

A pleated midi skirt.

Call it the eternal allure of back to school. A pleated midi skirt is a cornerstone of my fall wardrobe; if I were Olivia Rodrigo, I’d go for the mini cheerleader style, but these days I’m more of a midi girl. I like to wear them with a cropped crewneck sweater for a ‘50s vibe or a lace cami or vintage tee and cropped tweedy jacket. They’re perfect with heels, sneakers, and boots and if they’re long enough, you may be able to sneak a few extra days sans tights. 

06

Turtlenecks.

I think about turtlenecks like apple varietals: there’s something for everyone, and there are delicious options for all sorts of activities. At the very least, I believe you need a super tight classic black piece for layering, a cashmere or merino wool that can be dressed up or down, and a slouchy, super-soft version for cozy days. Black is always the icon but there’s much to be said for navy, evergreen, cream, and camel. Even my seven-month-old son has a turtleneck, that’s how much I love them. 

07

Hot pink or lemon yellow.

It’s easy to go full fall palette with reds, oranges, mustards, and darker jewel tones, but you know what looks fab with burgundy? Hot pink. What pops with camel? Bright yellow! Adding a hint of vivid color to your fall looks bridges the gap between summer and autumn and adds an unexpected dash of fun.

08

The cable-knit sweater.

Not quite ready for fall vibes yet? The cable-knit sweater understands and is here to gently hold your hand as you tiptoe into the pumpkin patch. Pretend you’re in your own version of When Harry Met Sally all season long with this cool-weather essential. Wear it with vintage Levi’s for a Harry-esque look or toss it on with leggings or a miniskirt and boots and pretend you’re Taylor Swift recording Folklore.

Kara Nesvig

Kara Nesvig grew up on a sugar beet farm in rural North Dakota and pretended to be Dorothy from The Wizard of Oz for about three full years. Things haven’t changed much, except she now lives in an adorable ’20s house in St. Paul with her husband, their Cavalier King Charles Spaniel Dandelion and many, many pairs of shoes. Kara is a voracious reader, Britney Spears superfan and copywriter — in that order.