As the new season begins, it’s time to start thinking about the best fall outfits. We drew inspiration from street style to make styling outfits a little easier. Here, you’ll find plenty of transitional outfit ideas to carry you through those in-between summer-to-fall days (Pro tip: layering is key).
Whether you’re wondering how to keep your favorite poplin skirt in rotation or increase the shelf life of your longline denim shorts, these tips and tricks are just plain smart. Plus, you’ll see how to incorporate fall’s biggest jacket trends (lots of suede and tailoring for starters) and all those runway-ready shoes, such as riding boots and satin slippers, just in time for those first few leaves to fall. Ahead, the nine best fall outfits to get you started.
Minimalism with a Twist
Stick with the staples, but with stylish tweaks. Trade out your tried-and-true straight-leg jeans for bootcut denim and wear them with a white T-shirt and collarless blazer—it’s a standout jacket trend for fall. Mesh flats and a work-ready tote bring a cool downtown attitude to this everyday outfit.
Mango Tailored Suit Blazer
Agolde Kick Bootcut Jeans
Reformation Britt Ballet Flat
Liffner Petite Penne Tote
Suede Simplicity
Upgrade your barn jacket to a suede version to face the cooler months. It will provide that extra dose of warmth you need on chilly days, plus looks ultra-sleek when styled with a cardigan, wrap skirt, and walkable riding boot (one of this season’s biggest shoe trends). Don’t forget the suede handbag either!
Nour Hammour Barn Suede Jacket
Everlane The Selfie Cardigan
Cos Twist-Detail Midi Skirt
The Row Nobilis Riding Boot
Tory Burch Romy Suede Hobo Bag
Black and Brown Combos
Mixing black and brown is no longer a fashion faux pas; we actually encourage blending the rich tones. To do it right, play with modern silhouettes and texture. Style a collarless jacket with a woven or pleated skirt and pair it with of-the-moment accessories like slingback pumps, a cord pendant necklace, and a suede handbag.
Jonathan Simkhai Marlowe Jacket
Massimo Dutti Long Flowing Pleated Skirt
Toteme Croc-Embossed Slingback Pump
Heaven Mayhem Julia Necklace
DeMellier London The New York Shoulder
Transitioning Shorts from Summer to Fall
If the hot and cold days of fall have you wondering what to wear, layering is the key. Longline denim shorts are a savior in transitional outfitting. Wear it with your favorite oversized blazer, a trend-forward lace-trimmed top, and knee-high boots to perfect the look. Shed the layers as needed when that afternoon heat hits.
Gap Longline Denim Shorts
Loeffler Randall Gia Knee High Boot
Now 18% Off
JW Pei Orla Weave Handbag
Mixing in Menswear Motifs
Plaids, tweeds, checks—they’re everywhere! Nothing feels more quintessential than these prints this time of year, and with pencil skirts being back in a big way, we recommend grabbing one in a traditional suiting fabric, like glen plaid or tweed, for a sharp, polished look. It looks so crisp when worn with a white button-up shirt, kitten-heeled pumps, and bold earrings.
Banana Republic The Everyday Shirt
Favorite Daughter Favorite Daughter The Meyer Skirt
Tony Bianco Cherry Kitten Heel Pump
Jenny Bird Sundra Earrings
Madewell The Shopper Tote
The Statement Coat
Update your outerwear game with one investment coat that can be worn over everything. A suede topper is a wise choice; it has a soft and luxurious look and feel for fall. As noted earlier, don’t be afraid to mix brown and black and play with texture in your look, like faux leather pants.
Massimo Dutti Long Suede Trench Coat
Theory Wool Crewneck Sweater
H&M Straight Coated Pants
Aeyde Helia Nappa Leather Black Heels
Cos Mini Studio Bowling Bag
Western Chic
Lean into the western trend that we saw throughout the summer months into autumn. Style your favorite plaid shirt with a pair of chunky moto boots and a denim tote bag.
A.L.C. Hazel Faux Fur Jacket
R13 Boyfriend Plaid Button-Up Shirt
Levi’s High Rise Slit Skirt
Play with Poplin
Your white poplin skirt doesn’t need to be tucked away, even when the temperatures turn. As seen here, extend its life through the season and style it with a long-sleeved turtleneck and peacoat. Add modern accessories, such as a power pump and coordinating handbag, to keep the skirt in rotation well into the fall.
Commando Butter Turtleneck
Khaite Cecilia Leather Pumps
Freja New York Mini Chrystie Shoulder Bag
Remixed Basics
A trench coat, a button-up shirt, and jeans are the makings of a foolproof fall outfit. However, with the help of a few stylish add-ons, you can make this combination even better. Add a pair of ballet flats in satin instead and a suede top-handle bag for more texture. It’s a classic and cool look without trying too hard.
Rag & Bone Icon Maxine Button Down Shirt
Miu Miu Satin Bow Ballerina Flats
