31 October Outfit Ideas That Are Equal Parts Comfy and Chic

You don‘t have to stow away those floaty, summery maxi dresses just yet. Rather than pair them with warm-weather sandals, try swapping in some classic loafers instead for a fresh, fun and autumnal twist.

Shop similar styles: DISSH Aria Knit Dress ($129); Tory Burch Jessa Loafers ($328); A New Day Tote Bag ($25; $21)

You don’t need to be a farmer or under the age of ten to get away with overalls. Look for a slim-fit pair in a clean wash and style it with graphic staples like chunky loafers or a slim-fit turtleneck tee in a jewel tone.

Shop similar styles: J.Crew Tissue Turtleneck ($40); We The Free Camilla Overalls ($148); Strathberry Min Ace Crossbody Bag ($455); Sam Edelman Christy Loafers ($150)

We love this cute styling trick for early autumn days when the temperatures are still warm. Be sure to swap sandals or backless mules for comfortable sneakers or ankle boots too to keep those fall vibes going strong.

Shop similar styles: Babton Emporia Sweater Vest ($110); Chelsea28 Dreamy Tiered Dress ($119; $96); Tretorn Loyola Sneakers ($70)

A super simple way to dress up a day-ready shirtdress is by adding a metallic chain belt. Of course, patent leather boots don’t hurt either.

Shop similar styles: ASOS Curve Shirt Dress ($60; $27); B-Low the Belt Maisie Belt ($178); Kate Spade New York Boxxy Bag ($498); By Far Stevie 42 Boots ($696)

Suit vests as shirts was one unexpected trend to come out of Copenhagen fashion week, but we’ve been seeing it again in both New York and Milan and feel confident it will also pop up in London and Paris, too. Look for one that isn’t too fitted nor too oversize and pair it either with matching suit trousers or another style of pants in a coordinating hue. Then, add in some punchy accessories to keep things fresh.

Shop similar styles: DISSH Rowan Vest ($122) and Norah Pants ($94); JW Pei Maze Bag ($129); M.Gemi The Esatto Heels ($328; $195)

This ‘90s style is back for fall 2022. And while you can wear it a la Rachel Green with a plain white tank and some heeled sandals, we prefer a more modern approach—with a sharp blazer, a cropped blouse and a funky handbag. And, OK, some ‘90s sandals, too.

Shop similar styles: Favorite Daughter Break Up Blazer ($298); Missguided Cropped Button-Up Shirt ($42); Boden Denim Midi Skirt ($98); Journee Collection Tallie Sandals ($50)

You might want to consider sneakers over sandals, but tucking a crisp white button-down into the waist of some comfy wide-leg trousers is a surefire way to look perfectly polished.

Shop similar styles: ADAY Something Cool Button-Up Shirt ($170); Lulus Spotted You Pants ($49); AllSaints Allington Straw Bag ($129); Keds Leather Sneakers ($70)

Remember when we used to layer dresses over our beloved boot-leg jeans in the early aughts? Yeah, this isn't quite that. Unbutton a midi- or maxi-length shirtdress to at least your waist (or a little higher if you want to show some skin) and then pull on a pair of jeans in a more modern silhouette, i.e., skinnies, mom jeans or a loose, straight leg.

Shop similar styles: Equipment Zelie Silk Shirtdress ($450; $315); Warp & Weft Mia Jeans ($98); Madewell Leather Belt ($48); Vagabond Edwina Boots ($240)

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: AYR The Airport Cardigan ($195); Nordstrom Rachel Leather Belt ($49); Closet London Pleated Skirt ($96); Jeffrey Campbell Geist Boots ($165)

Fall has arrived! Except for those afternoons when it feels like it really hasn’t. If the weather isn’t feeling quite as crisp or cold as you’d like, you can still embrace the season with a short-sleeve sweater in place of your usual long-sleeve turtleneck knits. Pair it with wide-leg pants that also feel seasonally-appropriate but offer plenty of air flow to keep you cool.

Shop similar styles: Quince Cashmere Short-Sleeve Sweater ($90; $45); Rails Marnie Pants ($248); Tkees Allegra Sandals ($85)

Deep dark blooms don't feel quite as "evening-only" when worn with a sporty striped T-shirt, now do they?

Shop similar styles: Kule Modern Stripe T-shirt ($68); Reformation Besse Dress ($248); Coach Tabby Shoulder Bag ($450)

Hot pink minis, platform heels and all things glittery ruled this past summer, but fall is all about giving Barbiecore a more polished makeover. Think tailored suits, cozy knits and flats or sneakers over sky-high heels.

Shop similar styles: Banana Republic Lido Wool Blazer ($229) and Lido Straight-Leg Pants ($150); J.Crew Ribbed Cashmere Sweater ($228); AllBirds Tree Flyers Sneakers ($160)

We love an all black getup, but to avoid looking too basic, be sure to add in at least one stand-out accessory, be it some oversize pearl earrings or a leopard-print tote.

Shop similar styles: Kenneth Jay Lane Gold and Pearl Earrings ($70); Naadam Merino Cashmere Cardigan ($175); M.M.LaFleur Horton Wool Pants ($295); Kate Spade new York All Day Tote Bag ($248); Rothys The Point Flats ($145)

Plaid and denim are classic fall must-haves, but rather than stick with a basic flannel shirt or pair of straight-leg jeans, why not shake things up a bit? A patchwork plaid blazer and asymmetrical denim dress have the same classic vibes but with a fresh new twist we can absolutely get behind.

Shop similar styles: Stella Nova Angie Shacket ($379); Free People New In Town Dress ($148); Reformation Mimi Buckle Heels ($298)

Oh, you thought fall was the time to revert back to all blacks and grays? Not so much. Make room for bright oranges, yellows, reds and purples instead.

Shop similar styles: LOFT Short-Sleeve Sweater ($55); Solid & Striped Vivienne Skirt ($198; $75); Looks Like Spring Simone Bag ($159; $115); Free People Wilder Ankle Boots ($178)

This preppy styling trick was spotted all over the place during New York Fashion Week, and is incredibly easy to pull off. Plus, with early fall’s fickle weather—mornings are frigid, afternoons are sweltering and there’s always a rain shower when you least expect it—it’s good to have a cute way to tote around an extra layer should you need one.

Shop similar styles: Universal Standard Cashmere Sweater ($98); AYR The Deep End Shirt ($125); Everlane The Relaxed Chino Pants ($98); Mix No. 6 Studded Flats ($50)

A tight bodysuit with an asymmetrical neckline is an inherently sexy look, but when paired with some loose trousers and sporty sneakers it feels much more appropriate for a casual afternoon lunch date.

Shop similar styles: Cole Haan Hooded Trench Coat ($375; $200); NBD Vanessa Bodysuit ($158); Eileen Fisher Lantern Pants ($158); Nike Blaze Low ‘77 Sneakers ($100)

Another great way to transition your lighter dresses to fall is with the help of some lug-sole Wellies and a chunky cropped sweater. Pro tip: Wear a shorter dress with taller boots or show a little skin between the top of a short rain boot and a longer dress to avoid being too weighed down by all that material.

Shop similar styles: Allude Wool and Cashmere Cardigan ($380); Mille V-Neck Plaid Dress ($354); La Canadienne Alfie Boots ($625)

Give your outfit an instant boost by slipping into a pair of faux-leather leggings instead of your usual matte cotton styles. Even if you accessorize with casual basics like an oversize flannel and lace-up Dr. Martens (instead of, say, a silky blouse and knee-high boots) you’ll look more put together.

Shop similar styles: Old Navy Plaid Shacket ($85); Spanx Faux-Leather Leggings ($98); Mango Quilted Bag ($60); Dr. Martens Leona Boots ($190)

Instead of sporting a thick sweater dress akin to an oversize sweatshirt, try one that’s a much thinner knit and has a lower hem. 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: Ulla Johnson Nathalie Sweater Dress ($695); Madewell Sydney Hobo Bag ($118); Dolce Vita Alaya Boots ($140)

Monochromatic dressing doesn't necessarily mean wearing all black. Have some fun with yellow, purple or Kelly green instead.

Shop similar styles: Quince Cashmere Sweater ($50); BDG Wide-Leg Jeans ($79; $40); Atoms 001 Sneakers ($159)

Chunky sweater + flowy floral dress + white ankle boots = the ultimate fall fashion moment.

Shop similar styles: Polo Ralph Lauren Turtleneck Sweater ($298); Lulus Floral Mesh Dress ($72); Mansur Gavriel Mini Bucket Bag ($595); Marc Fisher Ltd. Jarli Boots ($189)

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

Shop similar styles: Blank NYC Take Faux-Suede Jacket ($128); SEA New York Noah Dress ($425); Aerosoles East Side Loafers ($110)

Plaid minis are too school uniform and plaid A-line skirts are too close to kilt territory. But a pleated midi feels elegant and autumnal. Keep those polished vibes going with a simple black knit and gold chain necklace.

Shop similar styles: Cult Gaia Chain Necklace ($158); Modern Citizen Scout Wrap Sweater ($88); A.L.C. Eden Skirt ($395); Alohas Straps Chain Heels ($138; $117)

We all have a favorite pair of jeans and likely a favorite denim jacket too, so why not combine them to create one chic blue-wash ensemble? And don’t worry too much about trying to find matching washes—in fact, we often prefer if they clearly aren’t a perfect pairing.

Shop similar styles: Wash Lab Denim Sidecar Jacket ($148); Agolde Cherie High-Rise Jeans ($198); Tory Burch T Monogram Bag ($298; $259); Steve Madden Loreen Boots ($140)

What exactly is a shacket, you ask? A combination shirt jacket and our new favorite summer-to-fall transitional outerwear.

Shop similar styles: Wilfred Free Ganna Shacket ($198); United Colors of Benetton Wool Turtleneck ($94); Everlane Cheeky Split-Hem Jeans ($88; $44)

’Tis the season for velvet everything...almost. Start with a small touch, like some velvet flats, a wide headband or even a clutch for day. Even better if you opt for a more unusual hue like caramel brown or sunshine yellow over typical black.

Shop similar styles: Unilqo Corduroy Cropped Jacket ($50); Frank and Oak Wool Sweater ($100); Madewell Cali Demi-Boot Jeans ($138); ASOS Lake Velvet Flats ($40)

Just because you'd rather wear neutral tones from head to toe doesn't mean you can't add at least one bright splash of color. Even if it barely peeks out from under the hem of your trousers.

Shop similar styles: Ganni Ribbed Knit Scarf ($95); J.Crew Ribbed Cashmere Sweater ($138); SNDYS Hills Pants ($69); Anthropologie Ines Clutch ($90); Steve Madden Paula Heels ($80)

Transition your strappy summer dresses to fall with the simple addition of a long-sleeve top and some western boots.

Shop similar styles: Ulla Johnson Aurelia Turtleneck ($195); Cinq a Sept Veena Dress ($495; $372); Cuyana Double Loop Bag ($348); Tecovas The Annie Boots ($295)

Baggy pants and a jumbo knit don’t look nearly as disheveled when they’re made of leather and cashmere, right? 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 Cashmere Sweater ($599); Blank NYC Faux-Leather Pants ($88); Anthropologie the Frankie Clutch ($80); J.Crew Winona Loafers ($178)

Easiest (and chicest) Halloween costume ever. Feel free to go all out with your makeup, or tone it down with a few simple whiskers and a button nose.

Shop similar styles: Amazon Cat Ears ($8); Bleusalt Long-Sleeve Top ($128) and A-Line Skirt ($132); Madewell Elspeth Boots ($198)