Deciding to take another slice of cinnamon-apple pie is a no-brainer, but figuring out how to dress stylishly 31 days in a row? A bit more challenging. So we scoured the streets to find the most fashionable fall ladies, and now we’re sharing their best tips with you. Here, 31 fabulous fall outfits to inspire your October wardrobe (including a chic and easy Halloween ‘fit).
31 October Outfit Ideas That Are Equal Parts Comfy and Chic
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1. Swap Summery Sandals for Leather Loafers
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.
2. Try a Pair of Throwback Overalls
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.
3. Layer a Sweater Vest Over a Puff-Sleeve Dress
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 sneakers or ankle boots too to keep those fall vibes going strong.
5. Add a Chain Belt to Glam Things Up
5. Wear a Suit Vest as a Shirt
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.
6. Try a Denim Midi Skirt
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.
7. Combine a Few Loose Tailored Pieces
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.
8. Wear a Shirtdress Open Over Pants
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.
9. Style Your Cardigan as a Shirt
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.
10. Try a Short-Sleeve Sweater
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.
12. Transition Summer’s Barbiecore for Autumn
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.
13. Choose One Stand-Out Accessory
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)
14. Wear Unexpected Versions of Fall Staples
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.
15. Embrace Autumn’s Vibrant Hues
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.
16. Knot a Sweater Over Your Shoulders
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.
17. Balance a Sexy Bodysuit with Loose Trousers
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.
18. Pair a Chunky Knit and Wellies with a Lightweight Frock
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.
19. Swap Your Yoga Leggings for a Faux-Leather Pair
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.
20. Try a Knit Maxi or Midi
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.
22. Layer a Sweater Over Your Summer Midi
23. Swap Your Denim Jacket for Suede
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.
24. Rock a Plaid Skirt Like an Adult
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.
25. Combine Two Easy Favorites
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.
27. Start Breaking Out the Velvet
’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.
28. Add a Single Pop of Color
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.
29. Layer a Turtleneck Under a Denim Midi Dress
30. Sport Slouchy Separates in Luxe Fabrics
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.
31. Get a Little Catty
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.