21 Trendy Fall Outfits The Hottest Looks of the Season

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Sarah Koch

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Fall fashion, here we come! It’s that magical time of year when we can finally break out the cozy sweaters and cute boots without sweating buckets. As someone who’s been known to wear flip-flops until there’s snow on the ground, even I get excited about fall fashion.

Let’s face it, putting together trendy outfits can be overwhelming. That’s why I’ve teamed up with some seriously stylish friends to bring you 21 looks that’ll have you looking like a autumn goddess faster than you can say “pumpkin spice latte.”

From classic plaids to edgy leather, we’ve got something for every style personality. The best part? These outfits are so easy to recreate, you’ll be strutting your stuff in no time. So grab your PSL (no judgment here) and let’s dive into the hottest looks of the season!

1. Oversized Sweater and Leggings

Woman in oversized sweater and leggings for fall fashion

Comfort meets style in this classic fall combo. Pair a chunky knit sweater with your favorite leggings and ankle boots. Add a statement necklace for a touch of glam. It’s like wearing a hug all day!

2. Plaid Blazer and Jeans

Woman in plaid blazer and jeans for trendy fall outfit

Channel your inner Cher Horowitz with a plaid blazer. Throw it over a simple white tee and jeans for an instant dose of ’90s cool. Don’t forget to practice your “As if!” in the mirror.

3. Leather Jacket and Dress

Woman in leather jacket and dress for edgy fall look

Tough meets sweet in this edgy-feminine combo. Layer a moto jacket over a flowy dress for the perfect balance. It’s giving “I can kick butt and look cute doing it.”

4. Turtleneck and Midi Skirt

Woman in turtleneck and midi skirt for sophisticated fall outfit

Channel your inner Audrey Hepburn with this timeless duo. A sleek turtleneck paired with a flowy midi skirt is always chic. Add knee-high boots for extra sass.

5. Flannel Shirt and Skinny Jeans

Woman in flannel shirt and skinny jeans for casual fall style

Embrace your inner lumberjack (but make it fashion). An oversized flannel paired with skinny jeans is the ultimate cozy-cool combo. Perfect for apple picking or pretending to like pumpkin patches.

6. Sweater Dress and Knee-High Boots

Woman in sweater dress and knee-high boots for chic fall outfit

One and done! A sweater dress is the lazy girl’s answer to looking put-together. Add knee-high boots and you’re ready to conquer the world (or at least look good trying).

7. Denim Jacket and Maxi Dress

Woman in denim jacket and maxi dress for layered fall look

Summer dress, meet fall layering. Throw a denim jacket over your favorite maxi for an instant seasonal update. It’s like telling summer, “I’m not quite ready to let you go.”

8. Cardigan and Slip Dress

Woman in cardigan and slip dress for cozy fall fashion

Lingerie as outerwear? Yes, please! Layer a chunky cardigan over a silky slip dress for the perfect mix of cozy and sexy. It’s like wearing your pajamas in public, but make it fashion.

9. Monochrome Suit

Woman in monochrome suit for powerful fall look

Power moves only! A monochrome suit in a rich fall hue like burgundy or forest green screams “I’ve got my life together” (even if you don’t). Fake it ’til you make it, right?

10. Graphic Tee and Cargo Pants

Woman in graphic tee and cargo pants for edgy fall style

Embrace your inner ’90s kid with this cool-girl combo. A vintage-inspired graphic tee paired with cargo pants is the perfect mix of nostalgia and now. Add chunky sneakers for extra street cred.

11. Shacket and Leggings

Woman in shacket and leggings for trendy fall outfit

Not quite a shirt, not quite a jacket – it’s a shacket! This trendy hybrid is perfect for those “Do I need a jacket?” days. Pair with leggings for maximum comfort.

12. Sweater Vest and Button-Up

Woman in sweater vest and button-up for preppy fall look

Channel your inner grandpa (but make it fashion) with this preppy combo. Layer a sweater vest over a crisp button-up for instant academic chic. Don’t forget your reading glasses!

13. Jumpsuit and Ankle Boots

Woman in jumpsuit and ankle boots for effortless fall style

One-piece wonder! A utility jumpsuit is the ultimate throw-on-and-go outfit. Add ankle boots and you’re ready for anything from errands to drinks with the girls.

14. Turtleneck and Overalls

Woman in turtleneck and overalls for cute fall outfit

Embrace your inner child with this playful combo. Layer a turtleneck under denim overalls for a look that’s equal parts cute and comfy. Perfect for actual farm activities or just pretending.

15. Leather Pants and Chunky Knit

Woman in leather pants and chunky knit for edgy fall fashion

Edgy meets cozy in this cool-girl approved outfit. Pair sleek leather pants with a chunky knit sweater for the perfect balance of tough and soft. It’s like a hug for your legs!

16. Midi Dress and Moto Boots

Woman in midi dress and moto boots for feminine-edgy fall look

Mix sweet and edgy with this unexpected combo. A floral midi dress paired with tough moto boots creates the perfect contrast. It’s like your wardrobe can’t make up its mind (in the best way).

17. Corduroy Pants and Turtleneck

Woman in corduroy pants and turtleneck for retro fall style

Embrace the ’70s revival with this groovy duo. Wide-leg cords paired with a sleek turtleneck is giving major vintage vibes. Just add a lava lamp and you’re good to go!

18. Trench Coat and Jeans

Woman in trench coat and jeans for classic fall outfit

Channel your inner detective (or flasher, no judgment) with a classic trench. Throw it over jeans and a tee for an instant polish. Bonus points if you dramatically open it while saying “Just one more thing…”

19. Knit Dress and Tall Boots

Woman in knit dress and tall boots for sleek fall look

Sleek and chic, a fitted knit dress paired with tall boots is the ultimate “I tried, but not too hard” look. It’s like wearing a full-body sock, but make it fashion.

20. Shearling Jacket and Jeans

Woman in shearling jacket and jeans for cozy fall style

Embrace your inner teddy bear with a cozy shearling jacket. Pair it with jeans for the perfect mix of comfort and style. Warning: May induce excessive cuddling.

21. Sweater Set and Midi Skirt

Woman in sweater set and midi skirt for sophisticated fall outfit

Twin set, but make it 2023. A matching sweater set paired with a midi skirt is giving major “rich aunt” energy. Perfect for sipping martinis or judging your niece’s life choices.

And there you have it, folks! 21 fall outfits that’ll have you looking like a autumn fashion icon faster than you can say “PSL.” Remember, the best accessory is confidence (and maybe a pumpkin-scented candle). Now go forth and slay those fallen leaves!

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