31 October Outfit Ideas That Are Equal Parts Comfy and Chic
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.
1. Treat Your Face Mask as an Accessory
The easiest way to dress up a plain T-shirt and flowy pants is with accessories that pop. But that doesn’t just refer to headbands, handbags or statement earrings—it also includes face masks. Have some fun with your PPE, like Coterie member Ijeoma Kola, and invest in some pretty prints or unexpected fabrics.
2. Balance a Bodysuit with Loose Trousers
A tight bodysuit with an asymmetrical neckline is inherently sexy, but when paired with some loose trousers and sporty sneakers it feels much more appropriate for a casual afternoon lunch date.
3. Layer a Chunky Cardigan Over a Sexy Satin Slip
Whether you opt for a ‘90s-inspired slip dress or an actual nightgown, adding a chunky knit on top, like Shanna Battle’s retro cardigan, makes this super-comfy piece feel dressed up enough for dinner with a friends or a midday coffee run.
4. Try Subtly Printed Pants
Printed pants are majorly in this year, but bold checkerboards, lime green zebra stripes and pink plaid can feel a bit too Y2K for some folks. That doesn’t mean you can’t join in on the trend, however—just choose a pattern that plays with shades of one color. Wear them with clean, neat basics to make the trend feel modern and adult.
5. Keep It Simple with a One-and-Done Standout Piece
It could be a floral fall jumpsuit or a boldly printed dress à la Monroe Steele, but perhaps the easiest way to feel put-together is by slipping into a single statement garment and calling it a day.
6. Opt for 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.
7. Swap your yoga leggings for a chic faux-leather pair
Even a sweatshirt and athletic sneakers feel fancier when worn next to some luxe-looking faux leather. Isn’t that right, Olivia Jeanette?
9. 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.
10. Give Overalls a Shot
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 pair it with graphic staples like chunky loafers or a slim-fit turtleneck tee in a jewel-tone.
11. 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.
12. Ease Your Way Back Into Workwear
Despite more and more offices reopening, we’re not quite ready to suit up just yet. Instead of slim-fit trousers, opt for a loose or wide leg and layer them with a bright crew-neck and black sneakers. Keep your accessories sleek and minimalist to maintain a professional vibe.
13. 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's just a pair of cheeky socks.
14. Make a Plaid Shirt Feel Modern
Take a page from Coterie member Tyla-Lauren’s book and opt for checks in neutral hues (as opposed to the typical bright red), then layer your shirt over sleek dark-wash, boot-leg jeans and some stark white booties.
15. 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.
17. Mix Feminine Florals with Tough Booties
Chunky sole boots are trending this fall, but they can read a bit too military for everyday wear. Our trick is to pair them with a feminine floral blouse (floppy bow cuffs or a pussy bow highly encouraged) to create a balanced look that’s neither too girly nor too tough.
18. Upgrade Your Go-To Sweatshirt+Leggings Combo
Swap your faded, worn-in cotton leggings for ones in a thicker fabric with subtle shine, then replace your college hoodie with a half-zip in classic stripes. The result: A look that’s just as comfortable but infinitely more chic.
19. 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.
21. Or Opt for Cozy Cashmere Separates
We pretty much never say no a good coordinating sweatsuit, but we love Grace Atwood’s matching cashmere turtleneck and trousers—the coordinating Chanel bag doesn't hurt, either. This set is just as comfortable as your slouchiest loungewear, just more grown up and luxurious.
23. Return to an easy favorite
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? Take inspiration from Coterie member Natalia Levsina and keep your accessories minimal and neutral in color.
26. 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-waisted skirt and a chic belt.
27. Layer Pants Under a Flouncy Mini
Get more use out of a flirty minidress by layering slim-fit pants in a coordinating hue underneath. Structured fabrics work best here. If your dress is patterned try solid-hued pants, and vice-versa, then finish with simple black or white heels.
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, 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.
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.