33 Trendy Casual Fall Outfits for Women with Leggings

Fall is the perfect season to embrace comfort without compromising style, and leggings have become the ultimate wardrobe staple for creating effortlessly chic looks.

This comprehensive guide on 33 Trendy Casual Fall Outfits for Women with Leggings will transform the way you approach autumn dressing.

Whether you’re heading to a coffee date, running errands, or enjoying a weekend getaway, you’ll discover how to pair leggings with oversized sweaters, leather jackets, long cardigans, boots, and accessories to create polished, Instagram-worthy ensembles.

From monochromatic outfits to layered looks with scarves and statement coats, this article covers every style scenario to help you look fashionable while staying cozy throughout the crisp fall months.

1. Oversized Sweater and Black Leggings

The oversized sweater paired with black leggings is a timeless fall combination that delivers maximum comfort and style.

This effortless look works for virtually any casual occasion and can be dressed up or down depending on your accessories and footwear choices.

• Choose a chunky knit sweater in neutral tones like cream, camel, or gray for a classic autumn aesthetic
• Black leggings create a slimming silhouette and serve as the perfect base for this outfit
• Opt for high-waisted leggings to ensure full coverage when wearing shorter sweater styles
• Add ankle boots or sneakers to complete the relaxed vibe
• Layer a long pendant necklace to add visual interest to the simple silhouette
• Consider tucking in just the front of your sweater for a more polished appearance

2. Leather Jacket with Leggings and Combat Boots

Adding a leather jacket to your leggings instantly elevates the look from casual to edgy and fashion-forward.

This combination brings an element of sophistication while maintaining the comfort factor that makes leggings so appealing.

• A classic black or brown leather jacket pairs perfectly with both black and colored leggings
• Combat boots add an edgy touch that complements the leather jacket aesthetic
• Choose faux leather leggings for a cohesive textured look that amplifies the style
• Layer a simple fitted top or bodysuit underneath the jacket for a streamlined appearance
• Add a crossbody bag in a contrasting color to break up the monochromatic palette
• Consider wearing a graphic tee under the jacket for a more casual street-style vibe

3. Longline Cardigan and Leggings

The longline cardigan has become a fall fashion essential that pairs beautifully with leggings to create an elongated, flattering silhouette.

This combination offers versatility and works seamlessly for both casual outings and work-from-home days.

• Select cardigans that fall below the hip or reach mid-thigh for the most flattering proportions
• Neutral colors like taupe, charcoal, and burgundy work exceptionally well for fall
• Pair with fitted leggings to balance the oversized nature of the cardigan
• Add a belt at the waist to create definition and prevent the outfit from looking too shapeless
• Choose ankle boots or loafers to maintain the sophisticated aesthetic
• Layer a fitted tank or turtleneck underneath for temperature control and visual interest

4. Tunic Top with Patterned Leggings

Tunic tops provide the perfect length to wear with leggings, offering coverage while creating a balanced and stylish outfit. Pairing a solid tunic with patterned leggings adds visual interest without overwhelming the look.

• Choose tunics that fall at least to mid-thigh for appropriate coverage
• Floral, plaid, or geometric patterned leggings add personality to your fall wardrobe
• Keep the tunic solid-colored to let the patterned leggings be the focal point
• Add flat boots or ballet flats for a comfortable yet put-together appearance
• Incorporate a statement necklace or scarf to draw attention upward
• Consider fabrics like cotton blends or jersey for maximum comfort

5. Plaid Shirt and Leggings

The plaid shirt is a quintessential fall pattern that brings a cozy, cabin-inspired aesthetic to any leggings outfit. This combination channels rustic charm while remaining practical for everyday wear.

• Flannel plaid shirts in red, navy, or forest green capture the essence of autumn
• Wear the shirt open over a fitted tank top or button it up for a different look
• Black or dark-colored leggings ground the outfit and prevent it from looking too busy
• Add lace-up boots or hiking boots to enhance the outdoorsy vibe
• Tie the shirt at the waist for a more fitted silhouette and trendy appearance
• Layer a puffer vest over the plaid shirt for extra warmth and dimension

6. Denim Jacket and Leggings

A denim jacket paired with leggings creates a casual, all-American look that’s perfect for mild fall days. This combination is effortlessly stylish and works for a wide range of activities from shopping to lunch dates.

• Choose a classic blue denim jacket or experiment with black or white denim for variety
• Layer over a striped or solid-colored top for a timeless appearance
• Add white sneakers for a fresh, sporty look or ankle boots for more edge
• Accessorize with a scarf in fall colors to add warmth and visual interest
• Opt for distressed denim jackets for a more relaxed, lived-in aesthetic
• Consider oversized denim jackets for a trendy, boyfriend-style fit

7. Turtleneck and Leggings with Knee-High Boots

The turtleneck and leggings combination with knee-high boots is the epitome of sophisticated fall dressing. This outfit elongates the legs and creates a sleek, polished silhouette perfect for various occasions.

• Fitted turtlenecks in neutral colors like black, navy, or cream work best with this look
• Knee-high boots should fit snugly to the leg to maintain the streamlined appearance
• Choose leggings without seams or embellishments for a cleaner look
• Add a long coat or trench for an extra layer of sophistication
• Incorporate a structured handbag to elevate the overall ensemble
• Consider suede or leather knee-high boots for added texture and fall-appropriate materials

8. Hoodie and Leggings Athleisure Look

The hoodie and leggings combination embodies the athleisure trend that has revolutionized casual fashion. This comfortable yet stylish outfit is perfect for running errands, casual meetups, or active days.

• Choose oversized hoodies for a relaxed, trendy appearance
• Pair with high-waisted athletic leggings for a sporty, put-together look
• Add chunky sneakers or slip-on shoes for the complete athleisure aesthetic
• Opt for matching sets in complementary colors for a coordinated ensemble
• Include a baseball cap or beanie for added casual style
• Carry a backpack or sporty crossbody bag to maintain the athletic theme

9. Blazer and Leggings

Pairing a blazer with leggings creates a smart-casual look that bridges the gap between professional and comfortable.

This combination is ideal for casual Fridays, business-casual events, or days when you want to look polished without sacrificing comfort.

• Structured blazers in neutral colors like black, navy, or camel work best
• Choose high-quality, thick leggings that resemble dress pants rather than workout wear
• Add pointed-toe flats or low heels to maintain the sophisticated aesthetic
• Layer a simple camisole or blouse underneath the blazer
• Incorporate a structured tote bag or leather handbag to complete the professional look
• Consider longer blazers that provide additional coverage for a more balanced silhouette

10. Puffer Vest and Leggings

The puffer vest adds warmth and dimension to a leggings outfit while keeping your arms free for movement. This practical yet stylish combination is perfect for transitional fall weather and outdoor activities.

• Choose puffer vests in fall colors like olive, burgundy, or navy
• Layer over long-sleeved shirts or thin sweaters for temperature versatility
• Add hiking boots or sturdy sneakers for an outdoorsy, practical look
• Opt for fitted leggings to balance the volume of the puffy vest
• Include a beanie or headband for extra warmth and style
• Consider quilted or down-filled vests for maximum insulation on colder days

11. Sweater Dress Over Leggings

Wearing a sweater dress over leggings creates a cozy, layered look that’s perfect for chilly fall days. This combination provides extra warmth while maintaining a fashionable, put-together appearance.

• Choose sweater dresses that fall above the knee for proper proportions
• Layer thick, opaque leggings underneath for warmth and coverage
• Add over-the-knee boots to create a seamless, leg-lengthening effect
• Belt the sweater dress at the waist to define your silhouette
• Opt for chunky knit dresses in rich fall colors like rust, plum, or forest green
• Include a long pendant necklace or scarf to add visual interest

12. Poncho and Leggings

The poncho brings a bohemian, relaxed vibe to leggings outfits while providing warmth and coverage. This combination is perfect for casual weekends and creates an effortlessly stylish appearance.

• Choose ponchos in fall-appropriate patterns like Aztec, Fair Isle, or solid earth tones
• Pair with fitted leggings to balance the loose, flowing nature of the poncho
• Add ankle boots or short booties to ground the outfit
• Keep accessories minimal since the poncho itself makes a statement
• Layer a fitted long-sleeve shirt underneath for added warmth
• Consider fringed or tasseled ponchos for extra texture and visual interest

13. Chambray Shirt and Leggings

The chambray shirt offers a lighter alternative to denim while providing the same casual, approachable aesthetic. Paired with leggings, this creates a comfortable outfit suitable for various fall activities.

• Wear the chambray shirt open over a graphic tee or tank top
• Roll up the sleeves for a more relaxed, casual appearance
• Add sneakers or slip-on shoes for an easygoing vibe
• Incorporate a crossbody bag for hands-free convenience
• Tie the shirt at the waist for a more fitted, flattering silhouette
• Choose darker chambray shades for a more autumn-appropriate color palette

14. Teddy Coat and Leggings

The teddy coat has become a fall and winter must-have that adds texture and warmth to any leggings outfit. This cozy combination creates an effortlessly chic look that’s both comfortable and Instagram-worthy.

• Choose teddy coats in neutral colors like camel, cream, or brown
• Pair with fitted black leggings to balance the bulky texture of the coat
• Add ankle boots or sneakers depending on the desired level of dressiness
• Layer a simple turtleneck or fitted top underneath
• Keep accessories minimal to let the textured coat be the focal point
• Opt for oversized teddy coats for a more relaxed, fashion-forward appearance

15. Graphic Tee and Leggings with Sneakers

The graphic tee and leggings combination creates a youthful, casual look that’s perfect for running errands or casual hangouts. This outfit is all about comfort and personal expression.

• Choose graphic tees with fall-themed designs, band logos, or inspirational quotes
• Pair with classic black leggings for a versatile base
• Add your favorite sneakers in white, black, or colorful designs
• Layer a denim or leather jacket over the tee for cooler weather
• Incorporate a baseball cap or beanie for added casual style
• Carry a backpack or tote bag to complete the laid-back aesthetic

16. Shacket and Leggings

The shacket (shirt-jacket hybrid) has become a fall fashion staple that pairs perfectly with leggings. This versatile piece provides light layering while making a style statement.

• Choose oversized shackets in plaid, corduroy, or solid fall colors
• Wear buttoned up as a jacket or open over a fitted top
• Add combat boots or ankle boots for an edgy, fashionable look
• Layer over a bodysuit or fitted long-sleeve shirt
• Incorporate a belt to cinch the waist if the shacket is particularly oversized
• Consider wool-blend or fleece-lined shackets for extra warmth

17. Crop Top and High-Waisted Leggings

For milder fall days, pairing a long-sleeve crop top with high-waisted leggings creates a modern, athletic-inspired look. This combination is both flattering and comfortable.

• Choose long-sleeve crop tops in ribbed fabrics or soft cotton blends
• Pair with high-waisted leggings to ensure no midriff is exposed
• Add chunky sneakers or platform shoes for a trendy, sporty aesthetic
• Layer a jacket or cardigan over the crop top for cooler moments
• Opt for matching sets in complementary colors for a coordinated appearance
• Include minimal jewelry to keep the focus on the sleek silhouette

18. Trench Coat and Leggings

The trench coat brings sophistication and elegance to leggings outfits, creating a polished look perfect for dressier casual occasions. This combination proves that leggings can indeed be chic and refined.

• Choose classic trench coats in beige, navy, or black
• Pair with high-quality, thick leggings that resemble pants
• Add heeled ankle boots or loafers for an elevated appearance
• Layer a fitted turtleneck or blouse underneath the coat
• Incorporate a structured handbag to complete the sophisticated ensemble
• Belt the trench coat at the waist to create definition and structure

19. Button-Down Shirt and Leggings

A crisp button-down shirt paired with leggings creates a preppy, polished-casual look that’s appropriate for various settings. This combination balances professional and comfortable elements perfectly.

• Choose white, striped, or chambray button-down shirts for a classic appearance
• Tuck the shirt partially into high-waisted leggings for a more intentional look
• Add loafers, ballet flats, or ankle boots depending on the occasion
• Roll up the sleeves for a more relaxed, casual vibe
• Layer a vest or cardigan over the button-down for added warmth
• Incorporate a watch and simple jewelry for subtle sophistication

20. Faux Fur Vest and Leggings

A faux fur vest adds glamour and texture to a leggings outfit while providing warmth without the bulk of a full coat. This combination creates a luxurious yet casual fall look.

• Choose faux fur vests in neutral colors like gray, brown, or cream
• Layer over fitted long-sleeve tops or turtlenecks
• Pair with black or dark-colored leggings to ground the outfit
• Add ankle boots or knee-high boots for a cohesive appearance
• Keep accessories simple to let the textured vest be the statement piece
• Consider shorter vests for a more balanced proportion with leggings

21. Quilted Jacket and Leggings

The quilted jacket offers a sporty-chic alternative to traditional fall outerwear and pairs beautifully with leggings for an active, put-together look. This combination is both practical and stylish.

• Choose quilted jackets in fall colors like navy, olive, or burgundy
• Pair with athletic or casual leggings depending on your activities
• Add sneakers or ankle boots based on the level of activity planned
• Layer a hoodie or sweatshirt underneath for extra warmth
• Incorporate a crossbody bag or backpack for hands-free convenience
• Opt for water-resistant quilted jackets for practical protection against fall weather

22. Cowl Neck Sweater and Leggings

The cowl neck sweater adds elegance and coziness to leggings outfits with its draped neckline creating visual interest. This combination is perfect for casual yet refined fall occasions.

• Choose cowl neck sweaters in solid fall colors or subtle patterns
• Pair with fitted leggings to balance the volume of the sweater
• Add ankle boots or knee-high boots for a polished appearance
• Keep the neck area free of scarves to showcase the cowl detail
• Layer long pendant necklaces that sit inside the cowl for added style
• Consider lightweight cowl sweaters for layering versatility

23. Military Jacket and Leggings

The military jacket brings structure and edge to leggings outfits with its utilitarian details and fitted silhouette. This combination creates a fashion-forward look with practical appeal.

• Choose olive green, navy, or khaki military-style jackets
• Pair with black or neutral leggings for a cohesive look
• Add combat boots or ankle boots to enhance the military aesthetic
• Layer a simple tee or tank underneath the structured jacket
• Incorporate minimal accessories to keep the focus on the jacket details
• Consider jackets with brass buttons or epaulettes for authentic military styling

24. Color-Blocked Sweatshirt and Leggings

Color-blocked sweatshirts add visual interest and a sporty vibe to leggings outfits. This combination is perfect for casual days when you want to add a pop of color to your fall wardrobe.

• Choose sweatshirts with complementary fall colors like rust, mustard, and cream
• Pair with black or neutral leggings to let the sweatshirt be the focal point
• Add white or colorful sneakers to enhance the sporty aesthetic
• Layer a denim or bomber jacket over the sweatshirt for cooler weather
• Keep accessories minimal and sporty like baseball caps or beanies
• Opt for oversized fits for a trendy, relaxed appearance

25. Wrap Sweater and Leggings

The wrap sweater creates a flattering silhouette that pairs beautifully with leggings for an elegant yet comfortable fall look. This combination is perfect for days when you want to look put-together without much effort.

• Choose wrap sweaters that tie at the waist for a defined silhouette
• Pair with high-waisted leggings for the most flattering proportions
• Add ankle boots or ballet flats for a feminine touch
• Select fall colors like wine, forest green, or charcoal
• Layer a camisole underneath for extra warmth and coverage
• Consider cashmere or soft knit fabrics for maximum comfort

26. Utility Jacket and Leggings

The utility jacket with its multiple pockets and structured design adds functionality and style to leggings outfits. This combination is ideal for practical yet fashionable fall dressing.

• Choose utility jackets in olive, tan, or navy for authentic styling
• Pair with athletic or casual leggings depending on planned activities
• Add sneakers or hiking boots for a utilitarian, outdoor-ready look
• Layer a simple tee or tank underneath the structured jacket
• Utilize the jacket pockets for a hands-free, practical approach
• Consider jackets with drawstring waists for a more fitted appearance

27. Off-Shoulder Sweater and Leggings

The off-shoulder sweater adds a touch of romance and femininity to leggings outfits while remaining cozy and comfortable. This combination is perfect for date nights or casual social gatherings.

• Choose chunky knit off-shoulder sweaters in fall colors
• Pair with high-waisted leggings to maintain modesty and balance
• Add heeled ankle boots or over-the-knee boots for an elevated look
• Keep the neckline free of scarves to showcase the off-shoulder detail
• Incorporate statement earrings to draw attention to the exposed shoulders
• Layer a coat or jacket over the shoulders when heading outdoors

28. Striped Shirt and Leggings

The striped shirt is a timeless classic that brings nautical charm and visual interest to leggings outfits. This combination creates an effortlessly chic look that works for various casual occasions.

• Choose horizontal striped shirts in classic color combinations like navy-white or black-white
• Pair with black leggings for a streamlined, slimming appearance
• Add loafers, ballet flats, or white sneakers for a classic finish
• Layer a blazer or cardigan over the striped shirt for added sophistication
• Incorporate a crossbody bag in a complementary color
• Consider boat neck or three-quarter sleeve striped tops for varied styling

29. Cardigan Set with Leggings

A matching cardigan and tank set paired with leggings creates a coordinated, intentional look that’s both comfortable and stylish. This combination has become increasingly popular in the loungewear-meets-streetwear trend.

• Choose matching cardigan sets in fall colors like camel, sage, or oatmeal
• Pair with complementary colored leggings or stick with classic black
• Add slide sandals, mules, or sneakers depending on the occasion
• Button only the bottom buttons of the cardigan for a trendy appearance
• Layer delicate necklaces to add interest to the simple neckline
• Opt for ribbed or cable knit sets for added texture

30. Peacoat and Leggings

The peacoat brings naval-inspired sophistication to leggings outfits, creating a polished look suitable for dressier casual occasions. This combination proves that leggings can work in more refined settings.

• Choose classic peacoats in navy, black, or camel
• Pair with high-quality, thick leggings that resemble dress pants
• Add heeled ankle boots or knee-high boots for an elegant appearance
• Layer a turtleneck or fitted sweater underneath the coat
• Incorporate a structured handbag or tote for a complete look
• Button the peacoat fully for a more formal appearance or leave it open for casual styling

31. Suede Jacket and Leggings

The suede jacket adds texture and a touch of Western-inspired style to leggings outfits. This combination creates a trendy, bohemian look perfect for fall.

• Choose suede jackets in tan, rust, or chocolate brown for authentic fall styling
• Pair with black or dark-colored leggings to ground the outfit
• Add ankle boots or cowboy boots to enhance the Western aesthetic
• Layer a simple tee or fitted top underneath the suede jacket
• Incorporate fringe details or brass hardware for added visual interest
• Consider faux suede options for animal-friendly and easier-to-maintain alternatives

32. Belted Coat and Leggings

A belted coat adds structure and sophistication to leggings outfits while emphasizing the waist for a flattering silhouette. This combination is ideal for days when you need to look polished and put-together.

• Choose belted coats in classic colors like gray, camel, or black
• Pair with high-quality leggings in coordinating colors
• Add heeled boots or loafers for an elevated appearance
• Cinch the belt tightly at the waist to create definition
• Layer fitted tops or sweaters underneath for a streamlined look
• Consider wool-blend coats for warmth and structure

33. Monochromatic Outfit with Leggings

Creating a monochromatic look with leggings and matching tops creates a sleek, elongated silhouette that’s both modern and sophisticated. This styling technique makes leggings look more intentional and fashion-forward.

• Choose one color family and wear it from head to toe
• Vary textures within the same color to add depth and interest
• Add boots or shoes in the same color family to extend the line
• Popular monochromatic combinations include all-black, all-gray, or all-cream
• Layer different pieces in the same color for dimension
• Incorporate accessories in complementary shades to break up the look slightly

Choosing the Right Leggings for Fall

• Look for leggings made from thicker fabrics like ponte, fleece-lined, or faux leather
• High-waisted styles provide better coverage and create a more polished silhouette
• Seamless leggings offer a smoother appearance under longer tops and tunics
• Compression leggings maintain their shape throughout the day and provide a slimming effect
• Dark colors like black, charcoal, and navy are most versatile for fall styling
• Invest in quality leggings from reputable brands for better longevity and appearance
• Avoid leggings that are too thin or sheer, as they can appear more like workout wear
• Consider moisture-wicking fabrics if you’ll be transitioning from outdoor to indoor heated spaces

Fall Color Palette for Leggings Outfits

• Earth tones like rust, terracotta, and burnt orange embrace the autumn aesthetic
• Jewel tones such as emerald, burgundy, and navy add richness to fall wardrobes
• Neutral colors including camel, beige, and cream create sophisticated, timeless looks
• Deep colors like charcoal, chocolate brown, and forest green anchor fall outfits
• Consider incorporating plaid patterns that feature multiple fall colors
• Monochromatic schemes in fall-appropriate colors create cohesive, elongated silhouettes
• Mix textures within the same color family to add dimension to solid-colored outfits
• Accent neutral bases with pops of fall colors through accessories like scarves and bags

Conclusion

Mastering the art of styling 33 Trendy Casual Fall Outfits for Women with Leggings opens up endless possibilities for comfortable yet fashionable autumn dressing.

From oversized sweaters and leather jackets to sophisticated trench coats and cozy ponchos, leggings serve as the perfect foundation for creating versatile looks that transition seamlessly from morning coffee runs to evening gatherings.

The key to elevating leggings beyond basic athleisure lies in thoughtful layering, quality fabric choices, appropriate footwear, and strategic accessorizing.

By experimenting with different textures, proportions, and color combinations featured in this guide, you’ll develop a signature fall style that celebrates both comfort and fashion.

Remember that confidence is the ultimate accessory, so wear these outfits with pride and enjoy the cozy, stylish autumn season ahead.