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 in the year 2020 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. Give Your Shorts One Last Run
We love the look of some Bermuda or longer-hem shorts paired with a simple crew-neck sweater and classic strappy sandals for one last transitional ensemble before we go all-in on sweater weather.
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. Streamline Your Accessories
Rather than opt for all black clothing and contrasting accessories, why not flip the switch? We love how Liz Teich’s coordinating sandals, bag strap, sunglasses and even her face mask help to elevate a simple T-shirt and easy paper bag-waist pants.
Shop similar styles: Ray-Ban sunglasses ($154); Dara Senders face mask ($45); Pretty Connected face mask chain ($36); Vero Moda T-shirt ($35); Isabel Marant Étoile pants ($460); Johanna Maxham bag ($250); Birkenstock sandals ($150)
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. Answer the Call of the Wild
Leopard print has been the pattern of the moment and it doesn't look like it's going away any time soon. Follow in the footsteps of Coterie member Katie Sturino and coordinate your spots with an array of solid neutral hues, like washed black denim and a beige sweater.
12. Rock Your PJs All Weekend Long
Sleek accessories and clean white kicks are all you need to make the sweater and pajama pants you wore to bed last night totally appropriate for daytime. (Shh, it’ll be our little secret.)
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 with 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.
17. Cinch two loose pieces with a belt
Worried wearing an oversize knit and some loose-fit trousers might look a bit too baggy? Simply add a belt at your waist, like Coco Bassey. Be sure to choose a waist cincher that will stand out from the rest of your look, either in a contrasting color or with a bright buckle.
18. 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.
20. Mix Large Prints with Small
This is one cheeky way to play with proportions. Select a pattern, like polka dots or stripes, and commit to it by wearing a supersize version of the print and a miniature iteration.
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.
25. When in doubt add a blazer
A plain white tee, dark-wash skinnies and Converse kicks? Pretty casual. But a plain white tee, dark-wash skinnies, Converse kicks and an autumnal blazer? Now that’s a memorable look. (Thanks for the inspo, Lillian Babaian.)
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. Pair a Practical Tech Jacket with a Flirty A-Line Skirt
Pair your rain jacket or technical workout top with a flouncy midi for a look that’s both feminine and sporty, all at once.
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 your self 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.