22 Fall Outfits That Are Easy, Chic and Oh-So Comfy

Instead of sporting a thick sweater dress akin to an oversize sweatshirt, try one that’s a thinner knit and has a lower hem for a much more polished effect. If you want to add a jacket, stick either to cropped cuts that can show off your waist or long dusters that help to emphasize the lengthening line of your sweater dress.

Shop similar styles: L’Acdemie Gaela Knit Dress ($238; $174); JW Pei Gabbi Bag ($89); Everlane Glove Boots ($130)

Don’t put those summer staples in storage just yet—Nantucket-inspired blue-and-white stripes, straw totes, easy slide sandals and light-wash denim can all be made to work for early autumn. The key is to ensure you’ve got a couple classic fall staples in the mix by, say, swapping your striped button-up for a striped knit or cut-off shorts for ankle-length jeans.

Shop similar styles: Alex Mill Button-Back Sweater ($135); Summersalt Perfect Boyfriend Shirt ($75); Agolde Pinch Waist Kick Jeans ($188); Furla Meraviglia Straw Bag ($288); Tory Burch Double T Slide Sandals ($198)

Both ’90s fashion and Friends nostalgia are in full swing this fall, so why not combine the two and use the show’s most stylish character, Rachel Green, as your sartorial inspiration? Tall slouchy boots, pleated mini skirts, gray sheath dresses and, of course, hair that’s full of body and bounce are as chic now as they were when Rachel first wore them.

Shop similar styles: Sam Edelman Water-Repellent Trench Coat ($190); H&M Cropped Sweater ($30); Banana Republic Pleated Mini Skirt ($80; $60); Vince Camuto Parnela Boots ($239)

Offset the preppy vibes of a puffy-sleeve midi by wearing it with a tough pair of booties. To avoid being weighd down by a big skirt and chunky shoes, make sure to show ample skin between the top of the shaft and your hem. Midis work best with ankle boots, and minis or knee-length frocks work better with higher silhouettes.

Shop similar styles: GAP Puff Tiered Midi Dress ($98; $88); Copenhagen Studio Vitello Boots ($240)

You don’t need to be a farmer or under the age of ten to get away with overalls. Look for a slim-fit version in a clean wash and pair it with grown-up staples like chunky loafers or a fitted turtleneck tee in a jewel tone. And don’t forget to add a few glam touches like gold earrings or some oversize sunnies.

Shop similar styles: L.L.Bean Cotton Turtleneck ($35); Faherty Avenue Overalls ($178; $79); Tory Burch Kira Leather Crossbody Bag ($398); G.H. Bass & Co. Whitney Weejuns Loafers ($175)

This outfit combo is one of our absolute favorites and can be worn with just about any shoe in your arsenal. Pro tip: If you want to tuck in your sweater but find the material too heavy or thick for your lightweight silk skirt, try tucking the hem into the band of your bra instead.

Shop similar styles: Naadam Cashmere Sweater ($75); Lovers and Friends Madalena Midi Skirt ($); Birkenstock Arizona Sandals ($160)

We like to think of a jean jacket as the LBD of fall apparel. It goes with anything and everything in your wardrobe, but it looks particularly chic when worn with a leather skirt (pencil, A-line or otherwise). Plus, the addition of a classic white T-shirt tones down the innate sex appeal of leather.  

Shop similar styles: Rag & Bone Margot Jacket ($495); The North Face Half Dome T-Shirt ($25); Jonathan Simkhai Faux-Leather Wrap Skirt ($445); Sarto by Franco Sarto Visa Shoes ($130)

Transition from summer to fall by wearing cool-weather staples, like a trench and long trousers, with warm-weather favorites, like a white tank and fisherman sandals. So long as you opt for more neutral hues, you’ll look fabulously well put together rather than seasonally confused.

Shop similar styles: Ted Baker London Kayleeh Trench Coat ($495; $247); Bandier Willow Tank Top ($48); Everlane The Way-High Drape Pants ($118); Everlane Leather Fisherman Sandals ($125; $93)

How does one make woodsy outerwear and basic denim look polished? Just add some chic knee-high boots (preferably with a pointed toe and thin heel) and a posh top-handle bag and voilà! Now this is how city gals do cabincore.

Shop similar styles: Wilfred Free The Ganna Shacket ($228); Zella Live In Leggings ($59); Madewell Small Transport Bag ($158); Schutz Maryana Tall Boots ($238)

No need to invest in a whole new pair of cowboy boots just to get in on the Western trend. Simply layer a chambray shirt over high-waist jeans, cinch a wide-buckle belt around your waist and pull on your favorite tall black boots to finish.

Shop similar styles: Cloth & Stone Chambray Shirt ($98); B-Low the Belt Bri Waist Belt ($143); Agolde Nico Slim Jeans ($168; $152); Franco Sarto L-Tribute Boots ($159)

We’re definitely on board with any trick that instantly doubles our wardrobe (without taking up any precious space in our closet). If closing the bottom buttons of your cardi creates an unflattering buckling situation, simply unbutton as high as you need to go to smooth things out, then toss on a high-waist skirt and a chic belt.

Shop similar styles: State Cashmere Crewneck Cardigan ($135); Sancia Soli 35mm Belt ($109); Samsoe Samsoe Uma Pleated Skirt ($120); Blondo Laureece Waterproof Boots ($150)

Dress up a pair of trendy cargo pants by styling them with a sharply tailored blazer and some posh ballet flats. It will instantly make this super casual style feel more appropriate for work or a dinner date.

Shop similar styles: A New Day Double-Breasted Blazer ($38); Pull&Bear Cargo Pants ($46); Alohas Sway Leather Flats ($140)

Rather than reach for your go-to jean jacket yet again, try an easy suede style instead. Cropped cuts, like the above bomber jacket, are easiest to wear and look more casual than a blazer, wrap coat or trench.

Shop similar styles: Treasure & Bond Suede Bomber Jacket ($189); Cleobella Lucy Midi Dress (278$); Linea Paolo Margie Loafers ($120)

This easy wardrobe staple will never be out of style. Wear it with brown leather loafers and a coordinating handbag, a là Coterie member Babba Canales to make this casual ‘70s wardrobe staple feel a bit more posh and modern.

Shop similar styles: Rag & Bone Cargo Jumpsuit ($495); Madewell Sydney Leather Bag ($118); M.Gemi The Pastoso  Loafers ($228)

We’ll never grow tired of this classic fall combo. The white boots help lighten the whole look and prevent you from looking dowdy, but opting for brightly colored knits and florals and also has the same effect.

Shop similar styles: Polo Ralph Lauren Wool Sweater ($298); White House Black Market Wrap Skirt ($120); Mansur Gavriel Mini Bucket Bag ($465; $326); Altar’d State Cammy Boots ($70)

‘Tis the season for plaid, tartan and buffalo check. The easiest way to wear the pattern of the season is when it’s splashed across a classic, oversize blazer. Keep the rest of your outfit extra simple with a plain tee, easy blue jeans and a pair of timeless black booties. 

Shop similar styles: Maeve Double-Breasted Blazer ($170); Athleta Outbound T-Shirt ($54); Agolde '90s Straight Jeans ($198); Franco Sarto Pisa Boots ($150)

Baggy pants and a jumbo knit don’t look nearly as disheveled when they’re made of leather and cashmere, now do they? Add in a pair of smart loafers and a chic clutch and you’ve got yourself a look that’s as comfy as it is cool.

Shop similar styles: Anine Bing Rosie Cashmere Sweater ($599); Blank NYC Faux-Leather Joggers ($88); Mansur Gavriel Mini Cloud Clutch ($545); Franco Sarto Beck Loafers ($125)

A giant knit and skinny jeans run the risk of looking pretty basic (read: boring). But sleek leather booties and over-the-top earrings are really all you need to make this easy ensemble feel both fresh and fashion-forward. (A pop of bold color won’t hurt either.)

Shop similar styles: Electric Picks High Society Earrings ($98); Cece Puff-Sleeve Sweater ($89); RE/DONE ‘90s High-Rise Skinny Jeans ($275); Dear Frances Spirit Boots ($670)

Beige gets a bad rap as a “boring” color, but it can actually look incredibly chic. For example, the texture and structural silhouette of this turtleneck sweater gives a particularly luxe vibe, especially when worn with tailored trousers, crisp white kicks and a simple-yet-elegant coordinating handbag.

Shop similar styles: Banana Republic Oversize Merion-Cashmere Sweater ($250; $175); Reformation Vesta Pants ($178); Ree Projects Ann Mini Bag ($540); Koio Capri Leather Sneakers ($295)

The easiest way to mix mismatched prints is to pick ones that use the same color combinations—in this case navy blue and rust red. Plaid of all types and dark, moody florals are two of the most popular autumn patterns, so start with pairing these two classics and finish with some sleek ankle boots.

Shop similar styles: J.O.A. Fringed Plaid Sweater ($48); Polo Ralph Lauren Floral Tiered Skirt ($298; $200); Trotters Mika Moto Boots ($145)

Opt for a sleeker pair than the grays you usually wear to the gym, like a slim-fit cream set or camel rib-knit. Then finish with a long, tailored coat, some elegant jewelry and either sneakers or ankle boots, and no one will even notice you're wearing your pajamas out and about.

Shop similar styles: Lou & Grey Signaturesoft Sweatshirt ($70) and Sweatpants ($70); Gorjana Bespoke Necklace Set ($108); Halogen Belted Wool-Blend Coat ($225); New Balance 327 Sneakers ($100)

Update a Canadian tuxedo with white ankle boots, a cozy white turtleneck and tiny sunglasses for a look that’s more city gal and less ranch hand.

Shop similar styles: Levi’s Original Trucker Jacket ($98); Naadam Fisherman Turtleneck Sweater($195; $98); Levi’s 720 High-Rise Skinny Jeans ($98); Dagne Dover Landon Extra Small Bag ($110); Marc Fisher LTD Ulani Boots ($189)