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

ijeoma kola october outfit ideas
Ijeoma Kola

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.

Shop similar styles: Emijaa Jaaemil Co. headband ($65) and face mask ($32); Madewell T-shirt ($20) and pants ($88); Superga sneakers ($65); Kayu bag ($125)

october outfit ideas 8
Christian Vierig/Getty Images

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.

Shop similar styles: London Fog trench coat ($250; $150); Lovers + Friends bodysuit ($128); LAUDE the Label pants ($148); New Balance sneakers ($80)

shanna battle
Shanna Battle

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: Y.A.S. cardigan ($85); Lunya dress ($198); Boden shoes ($150; $105)

ocotber outfit ideas 9
Daniel Zuchnik/Getty Images

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.

Shop similar styles: Citizens of Humanity top ($178; $125); Sandro pants ($340; $204); Vans sneakers ($60)

monroe steele
Monroe Steele/Fashion Steele NYC

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: Mangishi Doll dress ($169); Shashi earrings ($48); BP sandals ($40)

woman wearing blue pants and a button down shirt
Christian Vierig/Getty Images

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); Tory Burch pants ($298; $209); BTB Los Angeles bag ($68); Vans sneakers ($65)

olivia jeanette
Olivia Jeanette

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 ($59); Everlane fanny pack ($35); Spanx leggings ($98); Adidas sneakers ($85; $50)

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

woman wearing a floral slip dress and stripe t shirt
Christian Vierig/Getty Images

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); Astr the Label dress ($98); Coach bag ($495)

woman wearing a bright orange skirt1
Christian Vierig/Getty Images

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: L.L.Bean top ($20); Acne Studios skirt ($350); Mansur Gavriel bag ($495); BCBGeneration boots ($189; $133)

woman wearing overalls and loafers
Kristin Sinclair/Getty Images

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); Pilcro overalls ($160); Kate Spade New York bag ($198); Sam Edelman loafers ($150)

october outfit ideas 3
Edward Berthelot/Getty Images

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.

Shop similar styles: Abercrombie & Fitch jacket ($420); Faithfull the Brand dress ($309; $185); Tory Burch shoes ($298)

october outfit ideas 4
Christian Vierig/Getty Images

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.

Shop similar styles: ASOS blazer ($50); Collusion T-shirt ($24); Theory pants ($295); Converse sneakers ($55)

single pop of color 1042118914
Melodie Jeng/Getty Images

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.

Shop similar styles: Amy Lynn dress ($109); Hysteria by Happy Socks socks ($14); ASOS bag ($26); Coach loafers ($150; $99)

tyla lauren gilmore
Tyla-Lauren Gilmore

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: Weekday shirt ($111); Outdoor Voices tank top ($58); Agolde jeans ($198); Marc Fisher Ltd. boots ($189)

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

woman wearing a knit dress
Christian Vierig/Getty Images

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.

Shop similar styles: Rachel Comey dress ($450); Steve Madden clutch ($49); Everlane boots ($120)

wear one color from head to toe 1025136862
Matthew Sperzel / Getty Images

16. 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: A New Day sweater ($25); Scotch & Soda jeans ($148); My Accessories bag ($35); APL sneakers ($200)

october outfit ideas 7
Kristin Sinclair/Getty Images

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.

Shop similar styles: Nordstrom trench coat ($149); MinkPink blouse ($89); Liverpool Los Angeles pants ($89); Aster boots ($225)

october outfit ideas 6
Edward Berthelot/Getty Images

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.

Shop similar styles: Bandier sweatshirt ($88); LETT leggings ($88; $35); Vince Camuto heels ($100)

october outfit ideas 2
Christian Vierig/Getty Image

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.

Shop similar styles: Monica Vinader necklace ($625); Autumn Cashmere sweater ($298); Riley & Rae skirt ($79); Alohas shoes ($180)

elevated track pants 1025100012
Christian Vierig/Getty Images

20. 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); River Island pants ($78); Tory Burch bag ($498)

grace atwood
Grace Atwood/The Stripe

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.

Shop similar styles: Naadam sweater ($125); and pants ($115); Michael Kors bag ($458; $344); Thousand Fell sneakers ($120)

jessie loeffler randall
Jessie Loeffler Randall

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 ($120); Mille dress ($268); Loeffler Randall flats ($250)

natalia levsina
Natalia Levsina

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: Gap jacket ($90; $36) and jeans ($60; $25); Boss clutch ($198); Tony Bianco sandals ($155)

october outfit ideas 10
Daniel Zuchnik/Getty Images

24. Layer a Turtleneck Under a Denim Frock

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

Shop similar styles: Lulus top ($48); Melissa Odabash dress ($398); Old West boots ($90)

october outfit ideas 5
Christian Vierig/Getty Image

25. Rock a Graphic Knit

Embrace this throwback Y2K trend, with a 2021 twist—opt for sleek accessories in sleek shapes and straight-leg jeans in dark washes.

Shop similar styles: Rhode sweater ($445); Warp + Weft jeans ($98); Cuyana bag ($245)

cardigan as shirt
Daniel Zuchnick/Getty Images

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 ($158); Ganni skirt ($215); Marc Fisher Ltd. boots ($189; $130)

october outfit ideas 1
Christian Vierig/Getty Images

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.

Shop similar styles: Violet Romance dress ($68); Cider pants ($24); Aldo boots ($130)

sundress sweater white boots 1038695834
Edward Berthelot/Getty Images

28. Transition Your Summer Midi

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

Shop similar styles: Eileen Fisher sweater ($358); The J. Peterman Company dress ($228; $124); Coach bag ($350; $159); Calvin Klein boots ($149)

woman wearing a shacket
Jeremy Moeller/Getty Images

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: Wilfred Free shacket ($198); Karen Kane turtleneck ($98); Citizens of Humanity jeans ($218)

woman wearing an oversize sweater and leather pants
Jeremy Moeller/Getty Images

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.

Shop similar styles: AllSaints sweater ($259); Mansur Gavriel clutch ($495); Wilfred Free pants ($148); Sarto by Franco Sarto loafers ($99)

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 ($49); Marc Fisher boots ($200)

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

PureWow may earn compensation through affiliate links in this story.

From Around The Web