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

‘Tis the season for lots of leather—namely, sleek leather trench coats. And nothing says fall quite like a burgundy coat. So, channel your inner Lorelai Gilmore and style it with an all-black outfit made up of straight-leg jeans, a turtleneck and a black crossbody bag.

Forget the outdated “rule,” because you can wear white after Labor Day. In fact, an off-white wide-leg trouser and striped tank top make an effortlessly chic transitional outfit for fall. Just make sure to balance your summer pieces with fall staples, like a brown leather tote and a Brat-approved green jacket.

Rainy weather calls for a trusty pair of rain boots, and there’s a way to dress them up so they look just as cute as your suede knee-high boots. Here’s how to do it: Elevate the sturdy shoes with a maxi denim skirt and a chic off-the-shoulder blouse. It’s relaxed yet stylish, keeping the essence of the weatherproof shoe.

A brown suede coat is going to be a hot commodity this fall, and for good reason, too. Luxurious and soft to the touch, use this season’s most coveted outwear to swap out your edgier leather jacket for a change, then pair it with matching mini skirt and shirt in a stark white hue, some strappy neutral sandals and sleek jewelry for a sophisticated yet sexy ensemble.

Last year we were all about the warm and durable barn coat, and I suspect we’re going to see more of it this year, except in denim. Lean into the blue palette by selecting a baby tee, acid wash jeans and a bag that are all in the same color family. Finally, opt for a cool-toned flat, like lavender, to make the outfit pop.

If you find the trend cycle to be hard to keep up with (same), don’t fret because there’s a way to make a few styles work in tandem without clashing, namely, a cherry red sweater, capri leggings and heels with socks. You’ll get the warmth from the cozy sweater and plush socks, and the fashion from the capri pants and floral heels. Take it up a notch with accessories and watch how you can transform your look by adding a thin belt, bowling bag and rounded sunglasses.

The easiest way to transform your summer cargo pants into a cool look meant for late-night drinks: Throw on a cropped oversize blazer and pointed-toe pumps, but make sure to stay true to the utilitarian vibes and wear a tank top underneath. It’s both laid back and elevated and blends a bright neutral white with a moody army green.

Prepare to be the life of the party the second you don a pair of leopard pants. If you’ve been keeping up with runway or celeb trends, then you know that the leopard print revival is upon us. It’s wild, animalistic nature adds levity and texture to toned-down pieces, like a mock neck sleeveless sweater and a black bag. Remember to let the print do all the talking for you, then keep everything else tame.

Never underestimate the power of staple basics. A trusty pair of jeans, a cozy sweater and a good handbag is enough to make you look polished, but this fall, it’s time to go a step further and switch up your usual denim cut with something new: the barrel jean. The dramatic balloon effect at the thighs adds a special flair that’s missing in your everyday outfit. Just make sure you French tuck your knit, that way it won’t overwhelm in tandem with the volume of the pants.

Instead of sporting a thick sweater dress akin to an oversize sweatshirt, try one that’s a thinner knit (and in a longer length) 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.

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 and cut-off shorts for ankle-length jeans.

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.

Offset the preppy vibes of a puffy-sleeve midi by wearing it with a tough pair of booties. To avoid being weighed 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.

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.

This outfit combo is one of my 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.

I 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.

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.

I know that the combination of a shirt and jacket can sometimes read too casual, especially if you wear your jeans and comfortable sneakers with it. So, how do you make your 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.

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. It’s giving Beyoncé’s Wild West.

I’m definitely on board with any trick that instantly doubles my wardrobe (without taking up any precious space in my 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.

Dress up a pair of trendy cargo pants by styling them with a sharply tailored blazer and some posh ballet flats. I predict that we are about to see the hourglass silhouette flourish this season, and its bespoke fit will instantly make this super casual style feel more appropriate for work or a dinner date.

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 above, to make this casual ‘70s wardrobe staple feel a bit more posh and modern.

I’ll never grow tired of this classic fall combo. Like a crisp sunny day or rain with blue skies, the unexpected combination of a chunky sweater, floral dress or skirt and white booties is the exact magic that makes this a perfect fall outfit.  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.

Now that fall is upon us, it’s time to embrace 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. 

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.

Word has it: Skinny jeans are going to come back in favor, which is great news for your fall outfits. I know that 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.)

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.

The easiest way to mix mismatched prints is to pick patterns 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 options, so start with pairing these two classics and finish with some sleek ankle boots.

Opt for a sleeker sweatsuit 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 comfy sneakers or ankle boots, and no one will even notice you're wearing your pajamas out and about.

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. It still incorporates your favorite denim staples you like to wear no matter the season, but the way you style it is what makes it fall-appropriate.