34 Cute Casual Fall Outfits for Women with Leggings

As the leaves begin to turn golden and the crisp autumn air settles in, there’s nothing quite as comfortable and versatile as leggings for creating effortlessly chic fall looks.

Whether you’re running errands, meeting friends for coffee, or enjoying a weekend adventure, leggings serve as the perfect foundation for countless stylish combinations.

In this comprehensive guide to 34 Cute Casual Fall Outfits for Women with Leggings, you’ll discover how to transform this wardrobe staple into sophisticated ensembles that balance comfort with style.

From cozy oversized sweaters to trendy leather jackets, we’ll explore outfit ideas that incorporate layers, textures, and seasonal colors to help you master the art of casual fall dressing.

Each look is designed to inspire your personal style while keeping you comfortable throughout the season’s changing temperatures.

1. Oversized Sweater and Ankle Boots Combination

The oversized sweater paired with leggings creates an effortlessly chic silhouette that defines cozy fall fashion.

This combination offers the perfect balance between relaxed comfort and put-together style, making it ideal for various casual occasions.

Choose a chunky knit sweater that falls mid-thigh to create a flattering proportion with fitted leggings.
Opt for neutral colors like camel, cream, or grey for versatile styling options throughout the season.
Select ankle boots with a small heel to elongate your legs and add sophistication to the casual outfit.
Layer a long pendant necklace over the sweater to add visual interest and draw the eye vertically.
Tuck the front of the sweater slightly into the leggings for a more polished, intentional look.
Complete the ensemble with a structured crossbody bag in leather or suede for autumn texture.

2. Longline Cardigan with Belt Detail

A longline cardigan transforms leggings into a sophisticated outfit by adding length and structure.

Cinching the cardigan with a belt creates definition and prevents the look from appearing too casual or shapeless.

Choose a cardigan that reaches at least knee-length to create elegant proportions with your leggings.
Use a wide leather belt to cinch at the natural waist for a flattering hourglass silhouette.
Layer a simple fitted tee or tank underneath to keep the focus on the cardigan’s draping.
Select cardigans in fall-appropriate fabrics like merino wool, cashmere blends, or thick cotton knits.
Coordinate your belt color with your shoes for a cohesive, intentional appearance.
Add ankle boots or knee-high boots depending on the cardigan length and overall aesthetic you’re creating.

3. Plaid Flannel Shirt and Combat Boots

The classic flannel shirt brings a relaxed, outdoorsy vibe to leggings while maintaining a trendy edge.

Paired with combat boots, this combination channels effortless fall style with a slightly grunge-inspired aesthetic.

Choose an oversized flannel for a relaxed fit that can be worn open, buttoned, or tied around the waist.
Layer over a fitted tank top or basic tee in a complementary solid color.
Roll up the flannel sleeves to three-quarter length for a more casual, lived-in appearance.
Select combat boots with interesting details like buckles or laces to add visual interest.
Incorporate black leggings to ground the look and let the plaid pattern be the focal point.
Add a beanie or baseball cap for an extra dose of casual cool that’s perfect for fall weekends.

4. Leather Jacket and Sneakers Ensemble

A leather jacket instantly elevates leggings from gym wear to street style staple.

Pairing this edgy outerwear with clean white sneakers creates a modern, urban look that’s both comfortable and fashion-forward.

Invest in a quality leather or faux leather jacket in classic black or rich brown tones.
Balance the jacket’s structured silhouette with fitted leggings to avoid overwhelming your frame.
Choose classic white sneakers for a fresh contrast against dark leggings and leather.
Layer a simple graphic tee or plain white tee underneath for effortless style.
Add minimalist jewelry like small hoop earrings or delicate chains to enhance without overpowering.
Consider high-waisted leggings to create a longer leg line when wearing a cropped jacket.

5. Tunic Top with Riding Boots

Tunic tops provide excellent coverage and create a balanced silhouette when styled with leggings.

Riding boots add an equestrian-inspired elegance that’s quintessentially fall.

Select tunics that fall to mid-thigh or slightly below for appropriate coverage and proportion.
Look for interesting details like asymmetric hems, side slits, or embroidered accents.
Choose riding boots in classic brown or black leather that reach just below the knee.
Ensure your leggings are opaque and substantial enough to wear as pants.
Add a long pendant necklace or scarf to create vertical lines and visual interest.
Coordinate your bag with your boots for a polished, cohesive appearance.

6. Denim Jacket Layered Look

The timeless denim jacket brings versatile style to leggings outfits throughout fall.

This classic piece works across various aesthetic preferences and can be dressed up or down depending on styling choices.

Choose a fitted or slightly oversized denim jacket depending on your preferred silhouette.
Layer over long-sleeve tees, henleys, or lightweight sweaters for temperature versatility.
Select darker wash denim for a more sophisticated evening-appropriate look.
Pair with colorful or patterned leggings to add personality to this classic combination.
Add ankle boots for a dressier vibe or sneakers for maximum casual comfort.
Incorporate a crossbody bag or backpack depending on your daily activities.

7. Cowl Neck Sweater and Booties

A cowl neck sweater adds sophisticated draping and texture to leggings outfits.

The relaxed neckline draws attention upward while maintaining comfort throughout the day.

Select sweaters with generous cowl necklines that drape elegantly without overwhelming.
Choose mid-weight knits that provide warmth without adding excessive bulk.
Pair with sleek ankle booties in suede or leather for refined finishing.
Allow the sweater to fall naturally over the hips rather than tucking for a relaxed silhouette.
Add simple stud earrings since the cowl neck provides sufficient visual interest.
Consider neutral color palettes for maximum versatility and sophisticated appeal.

8. Quilted Vest Layering Style

Quilted vests add dimension and warmth without restricting arm movement.

This practical layering piece transforms leggings into a perfectly balanced casual outfit ideal for fluctuating fall temperatures.

Choose fitted or slightly tailored vests that don’t add unnecessary bulk around the midsection.
Layer over fitted long-sleeve tops or lightweight sweaters in complementary colors.
Select vests in classic colors like navy, black, olive, or burgundy for versatile styling.
Pair with ankle boots or knee-high boots depending on the weather and your activities.
Add a knit beanie and scarf when temperatures drop foar cohesive layered styling.
Consider vests with functional pockets for practical everyday wear.

9. Boyfriend Blazer and Loafers

A boyfriend blazer brings unexpected sophistication to leggings, creating a smart-casual outfit perfect for casual work environments or lunch dates.

Loafers complete the polished yet comfortable aesthetic.

Select blazers with structured shoulders but relaxed overall fit for modern styling.
Choose classic colors like charcoal, camel, or navy for maximum versatility.
Layer over simple fitted tops to let the blazer be the statement piece.
Ensure leggings are high-quality with substantial fabric weight for a polished appearance.
Add leather loafers or mules for sophisticated finishing without sacrificing comfort.
Incorporate minimal jewelry like a watch or simple bracelet to maintain the refined aesthetic.

10. Hoodie and Puffer Jacket Combination

The hoodie and puffer jacket pairing creates ultimate casual comfort while maintaining street-style appeal.

This sporty combination is perfect for active fall days and cooler temperatures.

Choose a fitted or cropped puffer jacket to maintain proportion with leggings.
Layer a neutral-colored hoodie underneath for cozy warmth and casual style.
Select high-top sneakers or chunky trainers to balance the volume on top.
Opt for streamlined puffer designs rather than overly bulky styles.
Add a baseball cap or beanie for extra warmth and enhanced casual aesthetic.
Keep accessories minimal to maintain the sporty, relaxed vibe of this outfit.

11. Button-Down Shirt and Vest Combo

A classic button-down shirt layered under a vest creates preppy sophistication when paired with leggings.

This combination strikes the perfect balance between polished and comfortable.

Choose crisp white or striped button-downs for classic appeal.
Layer a fitted sweater vest in neutral or autumn colors over the shirt.
Leave the collar of the button-down visible for added dimension and interest.
Pair with loafers, ballet flats, or ankle boots depending on the occasion.
Roll the shirt sleeves to three-quarter length if the vest is sleeveless.
Add a structured tote or satchel bag to complete the polished aesthetic.

12. Poncho Style with Knee-High Boots

A poncho adds dramatic draping and bohemian flair to leggings outfits.

Knee-high boots ground the flowing silhouette and add sophistication to this relaxed style.

Select lightweight ponchos in fall colors like rust, burgundy, or forest green.
Layer over fitted turtlenecks or long-sleeve tees to prevent excessive volume.
Choose sleek knee-high boots to balance the poncho’s flowing proportions.
Ensure leggings are substantial and opaque for appropriate coverage with shorter ponchos.
Add simple jewelry since ponchos provide significant visual interest.
Consider belting some poncho styles at the waist for added definition.

13. Athletic Windbreaker and Running Shoes

An athletic windbreaker transforms leggings into a functional sporty outfit perfect for outdoor activities or casual errands.

This combination prioritizes comfort while maintaining contemporary style.

Choose windbreakers with modern color-blocking or subtle patterns for visual interest.
Layer over fitted athletic tanks or moisture-wicking tees.
Select technical leggings with performance features like compression or moisture management.
Pair with running shoes that coordinate with the windbreaker colors.
Add a sporty crossbody bag or backpack for carrying essentials.
Consider matching the windbreaker to your leggings color for a coordinated athletic look.

14. Chambray Shirt and Cardigan Layers

Chambray shirts provide a lightweight denim alternative that layers beautifully under cardigans.

This combination creates depth and visual interest while maintaining comfort throughout fall days.

Choose fitted chambray shirts that won’t add bulk under cardigans.
Layer a long, flowing cardigan over the chambray for relaxed elegance.
Leave the chambray partially unbuttoned to show a layered tank or cami underneath.
Pair with ankle boots or ballet flats depending on the formality desired.
Add a long pendant necklace visible above the chambray collar.
Consider rolling the chambray sleeves to show below the cardigan sleeves for dimension.

15. Graphic Tee and Bomber Jacket

A graphic tee adds personality while a bomber jacket brings structured style to leggings.

This youthful combination balances casual comfort with trendy urban appeal.

Select graphic tees with interesting designs, band logos, or artistic prints.
Choose bomber jackets in classic colors like black, olive, or burgundy.
Ensure the graphic tee is visible beneath the jacket when worn open.
Pair with clean white or black sneakers for streamlined styling.
Add minimal accessories to let the graphic tee be the focal point.
Consider tucking the front of the tee slightly for a more intentional silhouette.

16. Shacket and Thermal Top Pairing

A shacket (shirt-jacket hybrid) provides the perfect weight for early fall and adds trendy texture to leggings outfits.

Paired with a thermal top, this combination offers both style and warmth.

Choose shackets in plaid patterns or solid fall colors for seasonal appropriateness.
Layer over thermal henleys or waffle-knit tops for added warmth and texture.
Select shackets with functional pockets and button closures for practical wear.
Pair with hiking boots or combat boots for a rugged outdoor aesthetic.
Leave the shacket unbuttoned for a more relaxed, casual appearance.
Add a beanie or wide-brim hat to complete the autumn-ready look.

17. Turtleneck and Trench Coat Elegance

A fitted turtleneck paired with a classic trench coat elevates leggings to sophisticated heights.

This polished combination is perfect for more formal casual occasions or transitional weather.

Select fitted turtlenecks in solid colors that create a streamlined base layer.
Choose a classic trench coat in khaki, black, or navy for timeless appeal.
Ensure the coat length is balanced with the leggings proportion—knee-length works well.
Pair with sleek ankle boots or pointed-toe flats for refined finishing.
Add structured bags like totes or satchels to maintain the sophisticated aesthetic.
Consider belting the trench coat at the waist for added definition and polish.

18. Color-Block Sweatshirt and Slip-On Shoes

A color-block sweatshirt adds playful style to leggings while maintaining maximum comfort.

Slip-on shoes complete this easy, grab-and-go outfit perfect for casual fall days.

Choose sweatshirts with interesting color combinations that reflect fall tones.
Select quality sweatshirt materials that maintain shape without excessive pilling.
Pair with classic slip-on shoes in white, black, or coordinating colors.
Keep jewelry minimal since color-blocking provides sufficient visual interest.
Add a simple crossbody bag or backpack for casual functionality.
Consider high-waisted leggings to balance the sweatshirt’s relaxed fit.

19. Faux Fur Vest Statement Look

A faux fur vest makes a bold statement when paired with leggings, adding luxury texture and visual interest.

This eye-catching piece transforms simple leggings into a fashion-forward outfit.

Select faux fur vests in neutral colors or rich autumn tones for versatile styling.
Layer over fitted long-sleeve tops or turtlenecks to prevent overwhelming your frame.
Choose sleek ankle boots to balance the vest’s volume and maintain sophistication.
Keep the rest of the outfit simple to let the fur vest be the focal point.
Add minimal jewelry—perhaps simple studs or a delicate bracelet.
Consider vests that hit at hip length for the most flattering proportion with leggings.

20. Sweater Dress Over Leggings Approach

A sweater dress worn over leggings creates ultimate coziness while maintaining coverage and style.

This practical combination works beautifully for various casual fall activities.

Choose sweater dresses that fall to mid-thigh or slightly above the knee.
Layer leggings underneath for warmth, coverage, and the ability to move freely.
Select coordinating colors—dark leggings work with most sweater dress colors.
Pair with knee-high or over-the-knee boots for proportionate styling.
Add a long pendant necklace or scarf for additional visual interest.
Consider belting the sweater dress at the waist for added definition if desired.

21. Utility Jacket and Basic Tee Setup

A utility jacket brings practical style and multiple pockets to leggings outfits.

This versatile piece works across various casual settings while maintaining functional appeal.

Choose utility jackets in olive, khaki, or navy for classic military-inspired styling.
Layer over simple fitted tees in white, black, or grey for versatile foundations.
Select jackets with functional details like multiple pockets, drawstrings, or belts.
Pair with combat boots or hiking boots to complement the utilitarian aesthetic.
Add a canvas crossbody bag or backpack for cohesive practical styling.
Consider rolling up the jacket sleeves for a more relaxed, casual appearance.

22. Cashmere Wrap and Ballet Flats

A luxurious cashmere wrap adds refined elegance to leggings while providing warmth and comfort.

Ballet flats complete this sophisticated yet comfortable outfit perfect for various occasions.

Invest in quality cashmere or cashmere-blend wraps for luxurious draping and warmth.
Choose neutral colors like camel, grey, or cream for maximum versatility.
Layer over fitted tops to prevent excessive bulk under the wrap.
Pair with classic leather ballet flats in black or nude tones.
Add simple, elegant jewelry like pearl studs or a delicate gold necklace.
Carry a structured handbag to maintain the refined aesthetic of this outfit.

23. Peplum Top and Wedge Booties

A peplum top adds feminine flair and creates definition at the waist when styled with leggings.

Wedge booties provide height and elegance while maintaining comfort.

Select peplum tops in fall colors and interesting textures like knits or structured fabrics.
Choose styles with longer sleeves for autumn appropriateness and coverage.
Pair with wedge booties that provide height without the instability of stilettos.
Ensure leggings are high-waisted to sit flush with the peplum for a seamless look.
Add simple earrings or a bracelet to complement without competing with the peplum detail.
Consider neutral leggings colors to let the peplum top be the outfit’s focal point.

24. Pullover Hoodie and Duck Boots Combo

A classic pullover hoodie paired with practical duck boots creates ultimate casual comfort.

This combination is perfect for outdoor activities, errands, or relaxed weekend wear.

Choose quality hoodies in neutral colors or seasonal tones for versatile styling.
Select duck boots in classic tan and brown or modern color combinations.
Layer a fitted tank or tee underneath if you might remove the hoodie indoors.
Pair with leggings in coordinating colors for a cohesive casual appearance.
Add a beanie or baseball cap for extra warmth and enhanced casual style.
Carry a backpack or sporty crossbody bag to complete the practical aesthetic.

25. Asymmetric Hem Top and Ankle Strap Flats

An asymmetric hem top adds contemporary interest to leggings outfits through unique draping and lines.

Ankle strap flats provide secure, comfortable footwear with a touch of detail.

Choose asymmetric tops with interesting hemlines that create visual intrigue.
Select styles that provide adequate coverage in the back and sides.
Pair with sleek ankle strap flats that add detail without overwhelming.
Keep accessories minimal to allow the asymmetric design to be the focal point.
Consider monochromatic or tonal color schemes for sophisticated styling.
Add a structured bag to balance the top’s flowing asymmetric elements.

26. Teddy Coat and Platform Sneakers

A plush teddy coat adds cozy texture and warmth to leggings while making a bold style statement.

Platform sneakers provide height and contemporary edge to complete this trendy combination.

Select teddy coats in neutral colors like cream, camel, or brown for versatile wear.
Choose coat lengths that hit mid-thigh to knee for balanced proportions.
Layer over fitted tops to prevent excessive bulk under the voluminous coat.
Pair with platform sneakers in white or coordinating neutral colors.
Keep accessories simple since the teddy texture provides significant visual interest.
Consider high-waisted leggings to create a longer leg line with this cozy coat.

27. Longline Tunic and Chelsea Boots

A longline tunic provides excellent coverage and creates an elongated silhouette with leggings.

Chelsea boots add classic British-inspired style with easy slip-on convenience.

Choose tunics that extend beyond the hip for appropriate coverage and proportion.
Select styles with interesting details like side slits, textured fabrics, or prints.
Pair with classic Chelsea boots in black or brown leather for timeless appeal.
Ensure leggings are substantial enough to wear as pants with opaque coverage.
Add a long pendant necklace to create vertical lines and enhance the elongated silhouette.
Consider coordinating your tunic color with your Chelsea boot color for cohesive styling.

28. Cropped Sweater and High-Waisted Leggings

A cropped sweater paired with high-waisted leggings creates flattering proportions and modern style.

This combination highlights the waist while maintaining comfort throughout the day.

Select cropped sweaters that hit at the natural waist or just above.
Pair exclusively with high-waisted leggings to ensure no skin shows.
Choose fitted or slightly relaxed cropped styles depending on your preference.
Add ankle boots or sneakers to complete the proportionate, contemporary look.
Layer over a longer fitted tank if you want the option of showing less skin.
Consider cropped sweaters with interesting textures like cable knits or ribbing for added dimension.

29. Flannel Tunic and Riding Boots Style

A flannel tunic combines the casual comfort of flannel with the coverage of a tunic length.

Riding boots add equestrian sophistication to complete this perfectly balanced fall outfit.

Choose flannel tunics with longer hemlines that provide appropriate coverage.
Select classic plaid patterns in fall colors like red, navy, olive, or burgundy.
Pair with tall riding boots to balance the tunic’s longer length.
Layer over a fitted tank or tee in a coordinating solid color.
Add simple accessories since plaid provides sufficient visual interest.
Consider belting at the waist for added definition if the tunic is particularly oversized.

30. Sherpa Pullover and Hiking Boots

A cozy sherpa pullover brings ultimate warmth and texture to leggings.

Paired with sturdy hiking boots, this combination is perfect for outdoor adventures or relaxed casual wear.

Choose sherpa pullovers in neutral colors that coordinate easily with various leggings.
Select quarter-zip or half-zip styles for adjustable warmth and added visual interest.
Pair with supportive hiking boots for practical outdoor functionality.
Layer a fitted long-sleeve tee underneath for additional warmth if needed.
Add a beanie or headband for complete outdoor-ready styling.
Carry a backpack for essentials when wearing this adventure-appropriate combination.

31. Wrap Sweater and Moccasins

A wrap sweater creates feminine draping and adjustable coverage when paired with leggings.

Moccasins add comfortable, casual footwear with a touch of bohemian flair.

Choose wrap sweaters in soft, drapey knits that tie at the side or wrap around.
Select rich fall colors like rust, burgundy, or forest green for seasonal appeal.
Pair with comfortable moccasins in suede or leather for relaxed styling.
Ensure the wrap sweater provides adequate coverage and doesn’t gap open.
Add simple jewelry since the wrap detail creates its own visual interest.
Consider layering a fitted cami underneath for additional coverage and warmth.

32. Structured Coat and Pointed-Toe Booties

A structured coat brings sophistication and polish to leggings, elevating them beyond casual wear.

Pointed-toe booties add refined elegance and create a lengthening effect.

Choose structured coats in classic colors like camel, navy, or charcoal grey.
Select styles with tailored lines and quality fabrics like wool blends.
Pair with sleek pointed-toe booties that create a sophisticated finishing touch.
Ensure leggings are high-quality with substantial fabric for a polished appearance.
Add refined accessories like a structured handbag and minimal jewelry.
Consider belting the coat at the waist for added definition and elegance.

33. Turtleneck Bodysuit and Over-the-Knee Boots

A turtleneck bodysuit creates a sleek, streamlined base for leggings while staying securely tucked.

Over-the-knee boots add dramatic height and fashion-forward style.

Select fitted turtleneck bodysuits that create a smooth, seamless line with leggings.
Choose neutral colors that coordinate easily with various leggings and boots.
Pair with over-the-knee boots that fit properly without slouching or gapping.
Ensure leggings are substantial enough to wear under boots without bunching.
Add minimal accessories to maintain the sleek, streamlined silhouette.
Consider adding a long cardigan or coat for additional coverage and layering options.

34. Sweatshirt Dress and Sock Boots

A sweatshirt dress provides ultimate comfort while maintaining a put-together appearance over leggings.

Sock boots add contemporary style with their sleek, fitted silhouette.

Choose sweatshirt dresses in quality materials that drape well without excessive slouching.
Layer leggings underneath for warmth, coverage, and freedom of movement.
Select sock boots with low to mid-height heels for comfortable yet stylish wear.
Keep the color palette coordinated—darker leggings work best under dress styles.
Add minimal accessories since the oversized dress provides a strong silhouette.
Consider adding a belt over the sweatshirt dress for optional waist definition.

Conclusion

Creating stylish fall outfits with leggings has never been easier with these 34 Cute Casual Fall Outfits for Women with Leggings.

From cozy sweaters and structured blazers to trendy shackets and elegant coats, the versatility of leggings allows you to build countless combinations that suit your personal style and daily activities.

By focusing on quality pieces, balanced proportions, and thoughtful layering, you can transform simple leggings into sophisticated ensembles appropriate for various occasions.

Remember that the key to successful legging outfits lies in choosing substantial fabrics, pairing with tops that provide adequate coverage, and finishing with footwear that elevates the overall look.

Whether you prefer sporty-casual vibes or polished sophistication, these outfit ideas provide endless inspiration for embracing comfortable style throughout the autumn season.

With these combinations in your styling repertoire, you’ll confidently navigate fall fashion while staying comfortable, practical, and effortlessly chic in your favorite leggings.