14 Fall Outfits for Trendsetters: Fresh Season Ideas

Joanna Elizabeth

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Updated November 23, 2023

Fall Outfits
These fall outfits are made for trendsetters.

As autumn leaves shift from lively green to cozy hues of amber and crimson, fall outfits take center stage for anyone who follows fashion trends. Our closets morph into a vivid mosaic of fabrics, from cozy sweaters to casual jeans to fabulous skirts.

Each garment acts like a page in the unfolding fall narrative that enchants us, whether we’re striding down the streets of fashion-forward cities or strolling through small towns awash in autumnal splendor. Our chosen looks become a mirror, reflecting both individual taste and the natural rhythm of the season.

Fall Outfits

Bright Sweater & High-Waisted Pants: Bold & Balanced

Yellow Sweater High Waist Trousers Fall Outfits
A bright yellow sweater and high-waisted pants showcase a standout fall look. Photo: Delsignore / Deposit Photos

Step into fall with a burst of color and a dash of finesse. The bright sweater is the star of the show, turning heads and lifting spirits as the days grow shorter. But let’s notice its perfect partner: the high-waisted pants that add a tailored feeling.

The ensemble reaches new heights with the addition of a belt, cinching the waist and adding a layer of sophistication. Cat eye sunglasses also work for daytime outings. This look is a mood booster, a conversation starter, and a fall fashion win.

Plaid Skirt & Blazer: Preppy Chic

Plaid Jacket Long Skirt Fall Outfits
A plaid skirt and blazer redefine prep, uniting timeless academic flair with contemporary finesse. Photo: ChinaImages / Deposit Photos

Elevate your fall wardrobe with a nod to the preppy trend that’s sweeping the fashion world. Rock a plaid skirt that’s in a mid to maxi-length version, offering a modern twist that pairs seamlessly with high heels or knee-high boots.

The blazer brings some authority to your outfit. Accentuate the look with carefully chosen earrings and a petite handbag, adding just the right amount of flair. For those brisk mornings or gusty afternoons, a long shawl or scarf becomes more than an accessory when draped around your neck and shoulders.

Leather Jacket with Long Dress: Rebel Romance

Leather Jacket Long Dress Fall Outfits
Pairing a leather jacket with a long dress combines two different aesthetics for fall. Photo: AGCreativeLab / Deposit Photos

Imagine pairing a long dress in animal print with a sleek leather jacket. It’s a blend that captures both grace and grit, perfect for women who refuse to be boxed into one style.

Upgrade the outfit with a pop of color–think vibrant heels or boots in shades like neon pink or emerald green, which are stealing the spotlight this season. Accessories like a lengthy necklace and a tote bag add the finishing touches, making you look like you’ve just stepped off a high-fashion runway.

Trench Coat with Printed Accents: A Fresh Look

Trench Coat Boots Bag Fall Outfits
A trench coat with printed accents brings a trendy update to the classic outerwear piece. Photo: AndreaA. / Deposit Photos

The trench coat is a classic, and you can update the look this season. Instead of the usual beige or camel, opt for a light-colored version that defies expectations. Pair it with a basic white tee and mom jeans, but let your accessories do the talking.

Printed boots and a matching bag bring a lively twist to this classic look. The trench is your armor against the unpredictable fall weather-wind, rain, you name it. Round off the ensemble with understated gold jewelry as accessories.

Long Denim Skirt & Puff Sleeve Blouse: Prairie Glam

Blouse Long Denim Skirt Fall Outfits
The long denim skirt and puff sleeve blouse make a stylish nod to prairie glam, capturing the heartland’s aesthetic. Photo: AGCreativeLab / Deposit Photos

Turn heads with a long denim skirt and a puff-sleeve blouse. The skirt serves as a canvas, but the blouse steals the show, creating a dramatic silhouette that’s impossible to ignore.

Pair this look with black or navy blue boots and a Western-inspired belt to infuse a hint of prairie chic. It’s a look that captures the essence of the frontier spirit while making a bold fashion statement.

Bomber Jacket with Distressed Jeans: Casual Edge

Bomber Jacket Distressed Jeans Fall Outfits
A bomber jacket coupled with distressed jeans delivers an effortlessly casual vibe, ideal for the chillier days. Photo: elenarostunova / Deposit Photos

For a dash of edgy warmth this fall, why not try a bomber jacket paired with jeans? But here’s the twist: go for jeans that are distressed only at the hems. This keeps your legs cozy while still exuding that rugged appeal.

A basic tee works wonders underneath the bomber, letting the outer pieces shine. Footwear? You’ve got options. Sneakers lend a casual vibe, whereas high-heeled ankle boots elevate the entire ensemble. Or even sport mules so you can show off your pedicure. It’s fashion-forward yet practical, a perfect blend for the season.

Zip-Up Cardigan & Wide-Leg Pants: The Art of Layering

Sweater Pants Fall Outfits
Zip-up cardigans and wide-leg pants evoke the sophistication of layering, a skill refined through generations. Photo: AGCreativeLab / Deposit Photos

Let’s focus on a new trio that’s all about comfort and style. Start with a turtleneck as your base layer. Then, add a zip-up cardigan for that extra warmth and a touch of casual elegance. Wide-leg pants complete the ensemble, offering both comfort and a fashion-forward aesthetic.

It’s an outfit that’s as cozy as it is chic, perfect for those crisp fall or winter days. Whether you opt for Chelsea boots or your favorite flats, you’ll step out in a modern and timeless look.

Turtleneck, Skirt & Combat Boots: Modern Classic

Turtleneck Skirt Fall Outfits
Capture the old and new by rocking a turtleneck, skirt, and combat boots for a head-turning autumn look. Photo: AGCreativeLabs

Embrace the chill of fall with a look that’s both cozy and edgy. Begin with a turtleneck sweater, the height of autumnal comfort. Wear it with an A-line skirt, adding a feminine flair contrasting beautifully with the sweater’s snug fit.

But here’s where it gets interesting: combat boots. These boots infuse the outfit with a rebellious spirit, making it clear that you’re not one to be pigeonholed.

Denim & Polka Dots: Cute Autumn Style

Denim Jacket Polka Dot Skirt Boots Fall Outfits
The juxtaposition of denim and polka dots makes for a delightful fall look, subtle but far from mundane. Photo: AGCreativeLab / Deposit Photos

This outfit is one way to bring a playful and polished look to fall. A classic denim jacket serves as the cornerstone, offering a laid-back vibe that’s quintessentially autumn. It’s always great for the late summer.

But the real star here is the polka dot skirt, injecting a dose of whimsy into the look that you’ll love. Over-the-knee boots add a sultry edge, elevating the outfit from casual to captivating.

It’s a blend of textures and patterns that strikes a perfect balance, making you ready for anything the season throws your way.

Dressing for Different Fall Occasions

Ideas for Casual Occasions

Casual Fall Outfits
Casual fall occasions find their muse in easy, adaptable styles that suit spur-of-the-moment coffee runs and laid-back gatherings. Photo: AGCreativeLab / Deposit Photos

For those laid-back fall days, whether grabbing coffee with friends or running errands, comfort and style can coexist beautifully.

Everyday Looks: The magic lies in the mix-and-match game. Picture a cozy cable-knit sweater worn with distressed jeans for a relaxed and on-trend look. Or perhaps a floral skirt with a simple tee topped with a denim jacket. The endless combinations allow you to express your unique style while staying snug.

The Versatile Pieces: The building blocks of your casual fall wardrobe are sweaters, jeans, skirts, and dresses. A chunky turtleneck sweater can be your best friend on a chilly day, especially when paired with a flowing skirt and ankle boots.

Alternatively, a knit dress can serve as a one-piece wonder, needing little more than a pair of sneakers to complete the look.

Ideas for Work

Work Fall Outfit J Crew
For the work setting, opt for fall attire that balances professionalism with the season’s textured offerings. Photo: J. Crew

Your work wardrobe also needs to adapt for the fall. The challenge is maintaining a professional demeanor while incorporating the rich textures and colors that define fall fashion.

In formal work settings, the classics never fail. Tailored blazers and trousers in neutral tones offer a polished and minimal look. A matching suit can also do the trick. But don’t shy away from adding a touch of autumn with accessories. A silk scarf in a deep maroon or a leather belt in a rich brown can subtly enhance your ensemble.

Relaxed Work Fall Outfits
Ditch the jacket for a more relaxed workplace. Photo: AGCreativeLab / Deposit Photos

For those in more relaxed work environments, the options are broader. A pair of well-fitted, dark-wash jeans can be a game-changer when worn with a button-down shirt and a statement necklace in a business casual setting. The key is to understand the nuances of your workplace dress code.

Ideas for Events & Special Occasions

Velvet Dress Fall Outfits Reformation
When events call, dazzle in special occasion outfits like a velvet dress. Photo: Reformation

Fall fashion delivers a rich tapestry of elegant and trendy options when the calendar fills up with special events like Thanksgiving. Whether you’re attending a formal dinner, a lively party, or even a semi-formal wedding, the season provides ample opportunity to shine.

For an evening event, consider the allure of a velvet dress in a deep, luxurious hue like emerald green, ruby red, or royal blue. The fabric itself exudes elegance, while the rich color captures the essence of fall. Combine it with strappy heels and a clutch for a look that’s both timeless and seasonally appropriate.

Special Occasion Sweater Skirt Fall Outfits Reformation
A sleeveless turtleneck and long skirt work well for dressy occasions. Photo: Reformation

Skirts also offer a versatile base for many elegant outfits. Imagine a high-waisted, pleated skirt paired with a fitted lace blouse. Add some statement earrings and ankle boots, and you’ve got a sophisticated and on-trend ensemble.

Embracing Autumn Looks

It’s clear that fall outfits offer a versatile playground for fashion enthusiasts. The season invites us to experiment with layers, textures, and colors, allowing us to create looks as unique as they are cozy. 

Whether you’re updating your wardrobe with sustainable choices or incorporating global influences, the options are as endless as they are exciting. So, as the air turns crisp and the leaves start to fall, seize the opportunity to redefine your style. After all, fashion is not just about clothing; it’s about expressing yourself.


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