23 Casual Autumn Outfits for Women Over 40

Navigating the transitional season of autumn while keeping your style effortless and refined can sometimes feel like a sartorial challenge, especially for women over 40.

However, dressing stylishly and age-appropriately doesn’t have to be a daunting endeavor. The key lies in curating casual autumn outfits for women over 40 that are as comfortable as they are chic.

This post aims to dispel the myth that fall fashion over 40 is anything but fabulous, offering you timeless outfit inspirations that promise both style and function.

Expect to find a mix of autumn outfits for women that balance comfort and elegance, proving that fall outfits for 40 year old woman can be just as trendy and versatile as any.

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1. Cashmere Crewneck Sweater + Midi Skirt:

Embrace the elegance and comfort of a cashmere crewneck sweater paired with a midi skirt in either pleated or wrap style.

This combination offers a timeless appeal that suits any casual autumn occasion, making it a perfect choice for women over 40 seeking both style and warmth.

The softness of the cashmere provides a luxurious feel, while the skirt adds a touch of femininity and sophistication to your ensemble.

Opting for a pleated midi skirt will give your outfit a dynamic, flowing appearance, which is excellent for days when you want a bit of flair.

Alternatively, a wrap-style midi skirt offers a customizable fit and often features a tie at the waist, which can help accentuate your figure beautifully.

This outfit can be accessorized with simple jewelry and a pair of comfortable flats or ankle boots, creating a look that’s both practical and chic.

2. V-Neck Sweater + Tailored Ankle Pants:

Elevate your autumn wardrobe with a classic and sophisticated combination of a V-neck sweater and tailored ankle pants.

This pairing is perfect for women over 40 who are seeking a blend of comfort and elegance in their everyday attire. A V-neck sweater not only adds a touch of femininity to your look but also offers versatility in styling.

You can choose from a variety of materials such as soft wool or a wool blend, which provides warmth without compromising on style.

Tailored ankle pants are a fantastic choice for creating a streamlined silhouette. They flatter your figure while offering the flexibility to move comfortably throughout your day.

This style of pants typically sits just above the ankle, making them ideal for showcasing your favorite autumn boots or elegant flats.

Together, these pieces create an outfit that is both functional and fashionable. The V-neck sweater can be tucked in or worn loose, depending on your personal style and the occasion.

3. Cashmere Crewneck Sweater + High-Waisted Jeans:

For a seamless blend of comfort and style this autumn, consider pairing a cashmere crewneck sweater with high-waisted jeans.

This outfit choice is not only timeless but also incredibly flattering for women over 40, offering a chic way to stay warm during the cooler days of fall.

The cashmere crewneck sweater provides a luxurious softness that feels great against the skin, while its classic cut ensures it never goes out of style.

Choosing a sweater in a neutral color like beige, gray, or navy allows for maximum versatility, making it easy to mix and match with other pieces in your wardrobe.

High-waisted jeans are a superb choice for this outfit because they elongate the legs and accentuate the waist, creating a more defined silhouette.

They come in a variety of styles, from skinny to straight-leg, allowing you to choose the fit that best suits your body type and personal taste.

4. Turtleneck Sweater + Midi Skirt:

For a look that epitomizes both comfort and elegance this autumn, pairing a turtleneck sweater with a midi skirt is a fantastic choice for women over 40.

The turtleneck sweater is not just a staple for the cooler months but also serves as a stylish layer that keeps you warm and chic. Opt for a sweater in a soft material like cashmere or a fine wool blend to ensure it feels as good as it looks.

A midi skirt complements the turtleneck by offering a touch of sophistication and grace to your outfit.

This length is perfect for showcasing your favorite boots or elegant heels, adding a refined touch to your overall look.

When styling these two pieces together, consider the colors and textures. A monochrome palette can create a seamless and elongated silhouette, making you look taller and slimmer.

Alternatively, mixing textures such as a woolen sweater with a leather or satin skirt can add an interesting contrast to your outfit, making it stand out in a subtle yet impactful way.

Accessorize with minimalistic yet bold accessories like a statement watch or a sleek handbag to keep the outfit sophisticated and coordinated.

5. Long Sleeve Tee + Dark Wash Straight-Leg Jeans:

For a truly effortless yet stylish autumn ensemble, pairing a long sleeve tee with dark wash straight-leg jeans is a fantastic choice for women over 40.

This combination strikes the perfect balance between casual comfort and subtle sophistication, making it ideal for a variety of occasions, from a relaxed weekend outing to a more laid-back office environment.

The long sleeve tee is a versatile staple that can be layered under sweaters or jackets as the temperature demands. Choosing one in a soft, breathable fabric ensures comfort throughout the day.

Opt for classic colors like white, black, or navy for easy mixing and matching with other autumn wardrobe pieces.

Dark wash straight-leg jeans offer a flattering fit that isn’t just trendy but also timeless. They help elongate your legs, creating a sleek silhouette that works beautifully with the relaxed fit of the long sleeve tee.

This style of jeans remains a preferred choice for its ability to transition smoothly from casual to more upscale settings with the simple addition of accessories or a change of shoes.

6. Denim Jacket + Printed Midi Dress:

Elevate your autumn style with the chic and effortless pairing of a denim jacket and a printed midi dress. This outfit choice is perfect for women over 40, blending casual comfort with a touch of elegance.

The denim jacket adds a layer of warmth and a dash of rugged charm, making it an excellent choice for those crisp autumn days. Its versatile nature means it can be dressed up or down depending on the occasion.

The printed midi dress serves as a vibrant centerpiece to this ensemble. With a variety of prints available, from floral to geometric patterns, you can choose a style that best reflects your personal taste.

The midi length is particularly flattering, skimming the body and enhancing your silhouette, while also providing enough coverage to be appropriate for any event.

When combining these two pieces, consider the scale and color of the print on your dress to ensure it complements the denim jacket.

A smaller, subtler print can be more versatile, while a bolder, larger pattern can make a more striking statement.

This outfit can be accessorized with simple jewelry, such as a pair of elegant earrings or a delicate necklace, and finished off with comfortable footwear like ankle boots or ballet flats.

7. Flannel Shirt (tied at waist) + Boyfriend Jeans:

For a relaxed yet stylish look that’s perfect for autumn outings, consider pairing a flannel shirt with boyfriend jeans.

This outfit effortlessly combines comfort with a touch of rustic charm, making it ideal for women over 40 who appreciate both style and ease.

The flannel shirt offers a versatile and cozy option that can be styled in various ways, but tying it at the waist creates a flattering silhouette that accentuates your natural curves.

It also adds a playful, youthful vibe to your overall look. You can choose a flannel in classic plaids or opt for a more subdued solid color depending on your personal taste.

Boyfriend jeans are known for their relaxed fit, which ensures comfort throughout the day. They are slightly loose yet structured, making them a fantastic choice for casual wear.

The slightly baggy nature of boyfriend jeans contrasts nicely with the cinched waist of the flannel shirt, providing a balanced look that is not only stylish but also incredibly flattering.

8. Sweatshirt Dress (knee-length) + Tights:

For a cozy yet stylish look that’s perfect for the cooler autumn days, consider the combination of a knee-length sweatshirt dress with tights.

This outfit is ideal for women over 40 who want to remain comfortable while looking effortlessly chic.

The sweatshirt dress offers a relaxed fit, which makes it a great choice for casual outings or even a relaxed day at home.

The knee-length of the sweatshirt dress ensures it is versatile enough to be dressed up or down. You can opt for a plain dress or one with minimalistic designs such as stripes or a subtle print to keep the look sophisticated.

Tights can be chosen in a complementary color to create a cohesive outfit or in a contrasting hue for a bit of pop.

Footwear choices such as boots or stylish sneakers can complete this outfit, depending on the occasion.

9. Solid Color Cashmere Sweater + Tailored Trousers:

For a sleek and sophisticated look that marries comfort with professional flair, consider the classic pairing of a solid color cashmere sweater with tailored trousers.

This ensemble is a stellar choice for women over 40 who are looking to strike a balance between casual comfort and workplace-appropriate attire during the autumn months.

The cashmere sweater offers a luxurious softness that makes it a pleasure to wear all day long. Opting for a solid color such as navy, cream, or charcoal allows for effortless versatility and pairing with various accessories and outerwear.

The simplicity of the solid color also serves to highlight the quality of the material and the elegance of your overall look.

Tailored trousers complement the refined quality of the cashmere sweater perfectly. They provide a sharp silhouette that enhances your figure while maintaining comfort, thanks to their structured yet forgiving fit.

10. Long Sleeve Henley + Midi Skirt with Pockets:

For an outfit that perfectly marries casual comfort with a dash of sophistication, try pairing a long sleeve Henley with a midi skirt with pockets.

This combination is not only practical but also stylish, making it an excellent choice for women over 40 who want to look effortlessly chic during the autumn months.

The long sleeve Henley offers a relaxed yet refined look, ideal for those days when you want something easy to wear yet fashionable.

Its button detailing adds a subtle interest to your outfit, allowing you to adjust the neckline to suit your style or the occasion.

Choose a Henley in a soft fabric like cotton or a cotton blend for added comfort throughout the day.

Pairing it with a midi skirt that features pockets combines convenience with elegance. The pockets not only serve a practical purpose but also add a casual flair to your ensemble, making it ideal for a variety of settings, from a day at the office to an afternoon coffee date.

The length of the midi skirt is perfect for transitioning through the seasons, providing enough coverage to keep you warm while still showing off your favorite autumn footwear.

11. Shacket (Shirt Jacket) + Dark Wash Jeans:

For a relaxed yet undeniably stylish autumn look, pairing a shacket (shirt jacket) with dark wash jeans is a wonderful choice for women over 40.

This outfit effortlessly bridges the gap between casual and refined, making it perfect for a variety of occasions from a casual day out to an informal dinner.

The shacket serves as a versatile piece that combines the structure of a jacket with the comfort of a shirt. It’s lightweight enough to not feel bulky, yet substantial enough to provide warmth on a breezy autumn day.

Opting for a shacket in a neutral color like beige, olive, or navy allows for easy pairing with a wide range of tops and accessories.

Dark wash jeans are a staple in any wardrobe due to their flattering properties and the ability to pair well with almost anything.

For women over 40, they offer a sophisticated edge to casual wear, elongating the legs and slimming the silhouette, which is enhanced further when paired with a shacket.

The darker hue of the jeans also adds a touch of elegance, making the outfit suitable for both daytime and evening wear.

12. Cashmere Crewneck + A-Line Skirt (below the knee):

For a refined and effortlessly stylish autumn look, try pairing a cashmere crewneck sweater with an A-line skirt that falls below the knee.

This combination is a wonderful choice for women over 40, offering a balance of elegance and comfort that’s perfect for the cooler days of fall.

The cashmere crewneck sweater provides a luxurious feel and warmth, making it a staple in your autumn wardrobe.

Its timeless design ensures that it can be worn year after year, always looking as chic as ever. Choosing a sweater in a neutral shade like cream, grey, or camel can offer great versatility, allowing you to pair it with a wide range of colors and accessories.

An A-line skirt that falls below the knee is equally flattering, giving you a silhouette that is both classic and forgiving.

The slight flare of the A-line cut enhances your natural waistline and offers a bit of graceful movement as you walk.

This style of skirt can be found in various materials, from soft wool blends to more structured fabrics, providing ample opportunity to experiment with textures.

When styling these pieces together, consider adding a pair of opaque tights and ankle boots to keep warm and stylish.

13. Turtleneck Sweater + Wide-Leg Pants (tailored):

For a sophisticated and modern autumn look, consider the stylish pairing of a turtleneck sweater with tailored wide-leg pants.

This outfit is a fantastic choice for women over 40, blending elegance and comfort in a fashion-forward way.

The turtleneck sweater is a classic piece that offers both warmth and a sleek silhouette, making it a perfect top for the cooler months.

Its high neck provides an extra layer of coziness, while its streamlined fit allows for easy layering under jackets or coats. Choose a sweater in a soft material like merino wool or cashmere for a luxurious feel.

Tailored wide-leg pants are the ideal complement to the fitted turtleneck. These pants are known for their flattering cut that helps elongate the legs and streamline the overall silhouette.

14. Long Sleeve Thermal + Faux Leather Skirt (midi-length):

For a chic and comfortable autumn outfit that combines warmth with a touch of edgy style, try pairing a long sleeve thermal with a faux leather skirt that reaches midi-length.

This ensemble is perfect for women over 40 who want to maintain a stylish look while enjoying the cozy comfort that the season demands.

The long sleeve thermal serves as a great base layer, offering both warmth and a soft texture against the skin.

Its snug fit makes it an excellent choice for layering under heavier pieces without adding bulk, ensuring you stay comfortable throughout the day.

You can choose from a range of colors, but earth tones or classic neutrals like black, grey, or navy will give you the most versatility for mixing and matching with other autumn staples.

Pairing the thermal with a faux leather midi-length skirt adds a modern and sophisticated twist to your outfit.

15. Cashmere Beanie + V-Neck Sweater + Straight-Leg Jeans:

For a look that combines effortless style with cozy warmth, consider the classic trio of a cashmere beanie, a V-neck sweater, and straight-leg jeans.

This ensemble is perfect for women over 40 who want to maintain a casual yet chic aesthetic during the autumn months.

Starting with the cashmere beanie, this piece not only keeps you warm as the temperature drops but also adds a stylish flair to any outfit.

Its soft texture and comfortable fit make it an essential accessory for your autumn wardrobe. You can choose from a variety of colors to complement your personal style or opt for neutral tones like grey or beige for maximum versatility.

The V-neck sweater is a key item in this combination, offering both comfort and a touch of elegance. The V-neckline elegantly frames the face and is perfect for showcasing a favorite necklace or scarf.

Straight-leg jeans are the final component of this outfit, chosen for their flattering fit and classic appeal. They offer a slight stretch for comfort but maintain a structured look that enhances your silhouette.

16. Cardigan + Midi Slip Dress:

For a blend of comfort and timeless elegance this autumn, the combination of a cardigan and a midi slip dress is a superb choice for women over 40.

This pairing not only offers a stylish appearance but also provides versatility and warmth during the cooler days of the season.

The cardigan acts as a cozy layer that can easily be styled open or buttoned up depending on the weather and your personal preference.

Opt for a cardigan in a soft knit fabric to ensure it feels comfortable against your skin and drapes beautifully over the dress.

A longer cardigan can add a touch of drama and movement to your outfit, while a shorter style keeps things classic and neat.

A midi slip dress underlines femininity and grace, skimming your figure with its fluid fabric. It’s perfect for those who want to strike a balance between casual and sophisticated.

The midi length is particularly flattering and practical, allowing for an elegant display of your favorite autumn footwear—perhaps a pair of ankle boots or chic flats.

17. T-Shirt + Boyfriend Jeans + Leather Jacket:

For a casual yet edgy autumn look, combining a T-shirt, boyfriend jeans, and a leather jacket is an excellent choice for women over 40.

This outfit effortlessly marries comfort with a touch of rebellious style, making it perfect for those days when you want to feel both relaxed and chic.

Start with a basic T-shirt—a true wardrobe staple that offers endless versatility. Whether you opt for a classic white tee or a graphic print, the T-shirt serves as a great foundation for layering.

It’s easy to wear and can be styled in numerous ways, making it ideal for a casual day out or a more relaxed office setting.

Boyfriend jeans are known for their comfortable fit and slightly oversized style, which adds a modern twist to any outfit.

They are typically looser than traditional jeans, providing a breathable fit that is perfect for layering during the cooler autumn months.

The relaxed cut of boyfriend jeans also makes them incredibly flattering for a variety of body types, ensuring you look great from every angle.

18. Sweater Vest + Button-Down Shirt (layered) + Dark Wash Jeans:

For a smart-casual look that blends classic and contemporary styles, try layering a sweater vest over a button-down shirt, paired with dark wash jeans.

This outfit is an excellent choice for women over 40 who seek a comfortable yet polished ensemble perfect for various autumn occasions.

The sweater vest serves as a stylish focal point in this combination, adding a preppy touch to the overall look.

It’s a versatile piece that can be worn over different types of button-down shirts, from crisp white to patterned designs, depending on your personal style and the occasion.

Button-down shirts are a wardrobe staple that lend a sharp and refined look to any outfit.

When paired under a sweater vest, they create an elegant contrast and allow for flexibility in adjusting your style to be more formal or casual, depending on how you choose to accessorize or whether you opt to tuck the shirt into your jeans.

Dark wash jeans are chosen for their ability to streamline and elongate the legs, creating a flattering silhouette.

They bring a balance of sophistication and ease to the outfit, making it suitable for both casual outings and more dressed-up events. The darker color also makes them incredibly versatile, easy to match with a variety of tops and shoes.

19. Long Sleeve Tee + Cargo Pants (slim-fit):

For a blend of functionality and style, pairing a long sleeve tee with slim-fit cargo pants offers a versatile and comfortable choice for your autumn wardrobe.

This ensemble is particularly suitable for women over 40 who are looking for outfits that are both practical and fashionable.

The long sleeve tee serves as a perfect base layer, providing comfort and ease without compromising on style.

You can choose from a variety of colors to suit your personal taste, with options ranging from classic neutrals to bold hues.

The simplicity of the tee allows it to be easily dressed up or down, depending on your accessories and outerwear choices.

Slim-fit cargo pants are an excellent addition to this outfit, combining the traditional utility look with a modern twist.

The slim fit keeps the silhouette streamlined and flattering, while the multiple pockets add practicality and a rugged charm. Opt for cargo pants in earthy tones like olive, beige, or navy to stay in harmony with the autumnal palette.

To elevate this casual combination, consider pairing it with stylish ankle boots or casual sneakers, depending on your plans for the day.

You can layer with a cozy cardigan or a chic jacket as the weather demands, enhancing both warmth and style. Accessorizing with a simple belt can define your waist and add a polished touch to the overall look.

20. Cashmere Turtleneck + Midi Skirt (pleated):

For an effortlessly elegant autumn look, consider pairing a cashmere turtleneck with a pleated midi skirt. This combination is perfect for women over 40, offering a stylish ensemble that balances comfort with a flair of sophistication.

The cashmere turtleneck is a quintessential piece for the cooler months, providing warmth and a soft touch against the skin.

Its snug fit and high neck design not only keep you cozy but also add a sleek, polished look to your overall outfit. Opting for neutral colors like beige, gray, or classic black allows for easy pairing with various accessories and outerwear.

The pleated midi skirt adds a dynamic element to the outfit with its flowing lines and elegant movement.

The midi length is particularly flattering and practical, striking the perfect balance between coverage and style.

This type of skirt often features a cinched waist, which can help to accentuate your figure, providing a beautiful silhouette that is both comfortable and stylish.

When styling these pieces together, you can choose to tuck the turtleneck into the skirt to define your waist or leave it slightly loose for a more relaxed feel.

21. V-Neck Sweater + Straight-Leg Jeans (dark wash):

For a classic and versatile autumn look that you can wear on numerous occasions, consider the timeless combination of a V-neck sweater and straight-leg jeans in a dark wash.

This ensemble is not only stylish but also incredibly flattering for women over 40, offering both comfort and a touch of sophistication.

The V-neck sweater is a fantastic choice as it elongates your neckline and enhances your face’s natural contours.

Opting for a sweater in a soft material like cashmere or a fine wool blend ensures that it’s comfortable enough to wear all day long.

Choosing a neutral color such as beige, gray, or classic black allows for easy pairing with various accessories and outerwear, making it a versatile addition to your wardrobe.

Straight-leg jeans in a dark wash are equally essential for crafting an elegant casual look. They offer a more refined alternative to the typical lighter washes, making them suitable for both casual and slightly more formal settings.

The straight cut is particularly flattering, helping to elongate your legs and creating a sleek, streamlined silhouette.

22. Long Sleeve Henley + Corduroy Pants (straight-leg):

For a cozy yet stylish autumn ensemble, consider the classic pairing of a long sleeve Henley with straight-leg corduroy pants.

This outfit choice is perfect for women over 40 who appreciate both comfort and style in their daily wear.

The long sleeve Henley provides a relaxed, yet refined look that can easily transition from a casual day at home to an outing with friends.

Its buttoned placket adds a touch of classic detail that elevates the simple design, making it versatile enough to be dressed up or down.

Straight-leg corduroy pants are a great addition to your autumn wardrobe, offering both warmth and texture to your outfits.

The soft fabric of corduroy is ideal for cooler days, and its vertical ribbing will help elongate your legs, creating a flattering silhouette.

23. Turtleneck Sweater + Leather Pants (matte finish):

For a sleek and modern autumn ensemble, try combining a turtleneck sweater with leather pants in a matte finish.

This outfit choice is superb for women over 40, offering an elegant yet edgy look that’s perfect for a variety of occasions.

The turtleneck sweater provides both warmth and a refined aesthetic, making it a staple for the cooler months. Opting for a sweater in a neutral color like black, gray, or cream will allow for maximum versatility and ease of pairing with other accessories.

Leather pants with a matte finish are a bold yet sophisticated choice. They lend an air of contemporary chic to any outfit, and their textured appearance adds depth and interest to your look.

Final Thoughts

By embracing combinations from cashmere crewnecks with midi skirts to turtlenecks paired with leather pants, we’ve illustrated that the possibilities are not just abundant but also incredibly appealing.

Ending on a note that reiterates our initial thesis, style is indeed ageless, and the autumn season offers a perfect canvas to express this.

Each outfit suggestion serves as a testament to the fact that women over 40 can embrace the fall season with as much chicness and grace as any.