Cold weather might not be for everyone, but it’s hard to dislike anything about fall fashion. The leaves change color, the air gets a little crisper, and the moment comes to swap out summer shorts and dresses for chic jackets, cozy sweaters and chunky boots — cue the orchard visits and warm, cinnamon-spiced beverages.
Of course, seasonal changes are also a great opportunity to take inventory of your wardrobe, whether you want to streamline what you already have or find some new pieces that’ll last you many autumns to come. Whether it’s a versatile cashmere sweater or a new pair of super durable boots, we’re always advocates for investing in high-quality pieces that will last you much longer than just one season.
Ahead, we’ve rounded up 20 pieces for men and women that'll fit right into your fall wardrobe.
The Nene Slip Dress ($295; mmlafleur.com)
Slip dresses are one of our favorite pieces for effortless layering. This gorgeous, dark green option functions like a neutral, but is way more interesting than a run-of-the-mill black slip dress. The best part? It’s 100% silk and machine washable.
AGOLDE x Riley High Rise Straight Crop ($238; argentwork.com)
As someone who doesn’t love jeans, I’ve always been skeptical of investing in my denim. However, I’ve always heard that AGOLDE makes some of the best jeans you can get. After trying these, all I can say is that I get the hype. They’re structured yet comfortable, extremely flattering, and somehow, instantly fit like a glove. As part of a collaboration with fashion-forward women’s workwear brand Argent, these jeans feature a clean hem and Argent-exclusive wash for a slightly dressier look that’s totally appropriate for business casual offices.
Alia Chelsea Boot ($365; koio.co)
Chelsea boots are a year-round staple, but a new season is a perfect excuse to splurge on this classic shoe that will last you for years. Handmade in Tuscany from bronze- and silver-certified Italian leather, the quality of these boots from KOIO are unlike any other shoe I’ve ever had. After an entire year of wear, they basically look as good as new. They’re water-resistant, super comfortable thanks to the cushioned foam insole, and serve as an endless source of compliments.
The Cozy Stretch Turtleneck Dress ($148; everlane.com)
You can never go wrong with a sweater dress, and this option is one of our favorites. While it’s super cozy, comfortable and warm, it doesn’t look schlubby in the slightest. The high-quality material along with the stellar construction and universally flattering fit make for a gorgeous piece you’ll get tons of use from.
Balloon Sleeve Tee ($78; cuyana.com)
T-shirts are a layering staple, but there’s no reason to limit yourself to neutral colors and boxy cuts. This elevated, feminine tee has a chic scoop neck, puffed sleeves and a cropped length designed to work with high-waisted pants. The rich, dark orange color is very pumpkin spice—perfect for fall.
Utility Barrel Pant ($98; everlane.com)
I was convinced that I would never find a baggy pant that looked good on me—until I discovered these. Unlike other pants and jeans that follow the slightly oversized, slouchy look, these are anything but unflattering. The cinched waist and curved leg look great on all body types and sizes, and details like accent stitching and patch pockets give it a slightly edgier look.
Navy Bananica Maxi Dress ($255; farmrio.com)
Wearing a dresses with an eye-catching print is one of my favorite ways to make a statement without having to think much about my outfit at all. Simply put it on and add accessories! The color palette of this stunning piece feels very autumnal, and with the detachable belt you can wear it loose and relaxed, or cinched for that hourglass silhouette.
Rails Ellis Button-Down Shirt ($168; shopbob.com)
When it comes to white button-downs, we’re always looking for something a bit unique. This feminine take on the classic style is made from a lightweight cotton poplin, which gives the piece both structure and breathability. Layer it under a sweater vest or under a blazer—either way you can’t go wrong.
Siren Sweater Dress in Cortado Multi ($278; bailey44.com)
Is it a cardigan? Is it a dress? How about both! This multi-striped knit cardigan dress is everything you could ask for in a versatile yet eye-catching fall statement piece.
Standard Jumpsuit in Fine Wale Corduroy ($255; alexmill.com)
We’re suckers for a good jumpsuit, and this corduroy option is simply irresistible. The green color, abundance of pockets and chic construction makes this a winning statement piece.
Ansie Tall Boots ($295; vagabond.com)
When it comes to tall boots, I love a rounded toe and lower heel for that effortless cool-girl look. Of course, those features are also great for comfort and practicality. The retro-inspired silhouette of these boots from Vagabond are super on-trend, while the beige leather is unique while still mega wearable.
Plaid High Waisted Wide Leg Pants ($225; somethingnavy.com)
Plaid and fall fashion go together like apple pie and ice cream. These wide leg pants, made from a mid-weight suiting fabric, can easily be dressed up for the office or worn in more of a street-style fashion.
Mohair Fishermen Knit ($80; huckberry.com)
For the autumn days where you can forgo a jacket in place of a warm sweater, we’re huge fans of a fisherman knit. This gorgeous option from Huckberry is made from a wool and mohair blend that achieves that elusive, effortless slouch. The material is also extremely soft, which makes it a great option for both layering and wearing on its own.
The Quilted Barn Jacket ($229; bonobos.com)
This timeless quilted jacket is a true transitional piece. It’s water-resistant for extra protection, the quilted construction retains heat, and the corduroy details are an elegant touch that help to make this piece exceptional.
Single-Pleat 10-Wale Corduroy Pant ($69.50, originally $128; jcrew.com)
The single pleats on these relaxed corduroys are a stylish touch to this essential wardrobe pant.
Iron Ranger ($349.99; redwingshoes.com)
The quality of Red Wing shoes are unmatched, and this style is a best-seller and fan-favorite for a reason. The construction is essentially flawless, they’re incredibly durable, and once you break them in a bit, they’re extremely comfortable and supportive. They’re also surprisingly versatile and can easily be dressed up for different occasions.
The Felted Merino Half-Zip Sweater ($155; everlane.com)
A half-zip sweater is the ideal fall staple. It’s classic, handsome and endlessly versatile. This wool option is incredibly soft and warm, yet still durable.
Italian Stretch Chinos ($139; bonobos.com)
Take a classic dress pant, but make it fall! The combination of the polished construction of these chinos with the bold color is a perfect way to have fun with a more traditional wardrobe staple.
Clarks Wallabee Boot Maple Suede ($170; clarksusa.com)
When it comes to an easy, everyday shoe, we can’t recommend this boot from Clark’s enough. Not only is it comfortable and versatile, the simple style is also perfect for pairing with all types of outfits. The maple suede feels very fall and just looks like it was created to stomp around in the autumn foliage.
Legendary Whitetails Men's Tough as Buck Berber Lined Flannel Shirt Jacket (starting at $73.49; amazon.com)
This wool-blend shirt jacket is a fantastic way to effortlessly incorporate those quintessential fall colors into your wardrobe.
Prices are accurate and items in stock at time of publishing.