31 October Outfit Ideas That are Equal Parts Comfy and Chic

editor@purewow.com (PureWow)
·10 mins read

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.

RELATED: 7 Flattering Fall Outfits for Every Body Type

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.

Shop similar styles: Emijaa Jaaemil Co. headband ($65) and face mask ($32); Madewell T-shirt ($20); Club L London pants ($45); Keds sneakers ($55); Florabella bag ($106)

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.

Shop similar styles: Frank & Eileen sweater ($185); Liverpool shorts ($59); 3.1 Phillip Lim bag ($550; $413); Seychelles sandals ($99)

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.

Shop similar styles: For Love and Lemons cardigan ($172); Dannijo dress ($315); Journee Collection shoes ($35)

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.

Shop similar styles: New York & Company dress ($100; $50); Gorjana earrings ($60); Coach 1941 sandals ($150)

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.

Shop similar styles: Lyssé shirt ($108); La Vie Rebecca Taylor pants ($195); Vans sneakers ($50)

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?

Shop similar styles: Abercrombie & Fitch sweatshirt ($49); Everlane fanny pack ($35); Spanx leggings ($98); Nike sneakers ($140)

RELATED: The 10 Best Faux Leather Leggings to Buy Before Fall Arrives

8. Give Moody Florals a Sporty Spin

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

Shop similar styles: Tory Sport T-shirt ($128); Derek Lam 10 Crosby dress ($550; $330); Zac Zac Posen bag ($195)

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.

Shop similar styles: Lands’ End top ($40); French Connection skirt ($); Frame belt ($250); The Marc Jacobs bag ($295); Chinese Laundry boots ($80; $60)

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.

Shop similar styles: J.Crew turtleneck ($37; $22); Madewell overalls ($148); Tory Burch bag ($458); Louise et Cie loafers ($140)

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.

Shop similar styles: Charter Club sweater ($139; $111); J.Crew T-shirt ($118) and bag ($138); Topshop jeans ($80); Steve Madden boots ($110)

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.)

Shop similar styles: BP. sunglasses ($19); La Ligne sweater ($195); Honeydew Intimates pants ($48); Tory Burch bag ($458); Naturalizer sneakers ($79; $56)

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.

Shop similar styles: Mara Hoffman dress ($350); Bombas socks ($12); Thacker bag ($198); Frame loafers ($450)

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.

Shop similar styles: Marks & Spencer shirt ($125); BP. tank top ($10); Agolde jeans ($178); Aquatalia boots ($475; $333)

RELATED: 11 Flannel Outfits for a Stylish and Plaid-Filled Fall

15. Wrap yourself in a cardigan dress

Combine the best of both world—cozy sweaters and flirty frocks—with a cardigan midi dress, just like Coterie member Jasmine Crockett.

Shop similar styles: Naadam dress ($250); Dolce Vita boots ($80)

16. Elevate Some Comfy Track Pants

Get more use out of the gym staple by pairing it with a cashmere sweater and a structured mini bag.

Shop similar styles: Scotch & Soda sweater ($165); Aje pants ($295); Tory Burch bag ($598)

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.

Shop similar styles: Vero Moda sweater ($59); Halogen belt ($39); Liverpool pants ($98); Louise et Cie shoes ($120)

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.

Shop similar styles: Naadam sweater ($195); and pants ($185); Chanel bag ($5,300); Vince sneakers ($195)

19. 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.

Shop similar styles: Banana Republic dress ($139; $97); Coach clutch ($175); Everlane boots ($156)

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.

Shop similar styles: Mud Pie sweater ($60); LOFT skirt ($70; $55); Charles & Keith bag ($69; $49); Steve Madden sandals ($70)

21. Go all in on a single color

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

Shop similar styles: ASOS sweater ($40; $29); Gap jeans ($60; $24); Strathberry x Miffy bag ($555); Veja sneakers ($120)

22. Start breaking out the velvet

’Tis the season for velvet everything, starting with a pair of gorgeous burgundy ballet flats, á la Jessie Loeffler Randall.

Shop similar styles: Chimi sunglasses ($99); Mille dress ($258); Miu Miu flats ($525)

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.

Shop similar styles: Gucci sunglasses ($550); Forever 21 jacket ($35; $24); American Eagle Outfitters jeans ($40; $28); Sole Society clutch ($55); Jeffrey Campbell sandals ($135)

24. Combine Tough Boots with Quilting

Proof that opposites really do attract, this combination of lug-sole Chelsea boots and a grandma-inspired quilted coat is just the right level of quirky.

Shop similar styles: Dolan jacket ($288; $130); Sea dress ($385); Madewell boots ($188)

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.)

Shop similar styles: ASOS blazer ($56); Marine Layer T-shirt ($39); B-Low the Belt belt ($105); Re/Done jeans ($250); Converse sneakers ($50)

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.

Shop similar styles: Enza Costa cardigan ($156); Cult Gaia belt ($148); P.A.R.O.S.H. skirt ($405); Vince Camuto boots ($150)

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.

Shop similar styles: Topshop jacket ($68); Madewell skirt ($88; $60); Moschino bag ($345; $147); Charles David heels ($199)

28. Transition Your Summer Midi

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

Shop similar styles: Caslon sweater ($59); AllSaints dress ($305; $152); Mansur Gavriel bag ($610); Madden Girl boots ($70)

29. Embrace the Shacket

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

Shop similar styles: H&M shacket ($70); Autumn Cashmere turtleneck ($385); Frame jeans ($220; $110)

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.

Shop similar styles: AllSaints sweater ($260; $208); Mansur Gavriel clutch ($495); Wilfred pants ($148); Sam Edelman loafers ($140)

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.

Shop similar styles: Amazon cat ears ($9); White Mark dress ($30); Marc Fisher boots ($200)

RELATED: Fall’s Color Trends Are Proof Nobody's Getting Too Crazy with Fashion This Year