Finding casual fall outfits that feel comfortable and stylish matters as you move into your 40s. Maybe you’re after clothes that fit your lifestyle, give you confidence, and work for all sorts of occasions.
With the right mix of pieces, you can create fall looks that are practical and modern. Dressing for your needs and showing off your personal style gets a whole lot easier.
This guide helps you explore options that are simple to put together and feel great to wear all season long.
1. Chunky knit sweater with straight-leg jeans
A chunky knit sweater keeps you warm and looks stylish during fall. Pair it with straight-leg jeans for a classic and comfortable outfit.
Choose neutral or muted colors for a timeless look. Finish with simple sneakers or ankle boots.
Add a light jacket if you want extra warmth. You can wear this for just about any casual outing.
2. Tailored blazer over a silk blouse and tapered pants
Try a tailored blazer layered over a silk blouse for a polished yet easy look. Pair these with tapered pants for a flattering fit.
The blazer shapes your waist and adds style. A silk blouse brings soft texture.
Tapered pants give you a balanced outline. Change up shoes or jewelry if you want to shift the vibe from relaxed to dressy.
3. Long cardigan paired with a midi dress
A long cardigan over a midi dress feels comfortable and looks stylish for fall. The cardigan adds warmth and a polished layer without feeling heavy.
Pick a solid-colored dress and a textured knit cardigan. Add flats or boots to finish your look.
This outfit fits for work, errands, or weekends when you just want to feel put together without a lot of effort.
4. Turtleneck and leather leggings
A turtleneck with leather leggings makes a simple fall outfit that feels both classic and a little modern. Choose a fitted or slightly loose turtleneck for warmth and style.
Leather leggings add a polished look while staying comfortable. Finish with ankle boots or flats for an easy, put-together vibe.
This works for errands, lunch, or even a casual evening out.
5. Checked flannel shirt with dark wash jeans
A checked flannel shirt with dark wash jeans is simple and classic. This look feels comfortable for laid-back fall days.
Tuck in your shirt or leave it loose, depending on your mood. Dark wash jeans give a clean feel and pair well with many shoes.
Try ankle boots or clean sneakers to finish your outfit. If it gets chilly, toss on a light jacket.
6. Wool wrap coat over a cashmere sweater dress
Pair a wool wrap coat with a cashmere sweater dress for a classic fall look. The wool coat gives you warmth and structure.
The cashmere dress feels soft and comfortable. Choose neutral colors like camel, gray, or navy for versatility.
Add simple boots or flats. This combo works for work or weekend outings.
7. Soft cashmere pullover with culottes
A soft cashmere pullover feels comfortable and looks polished for fall. Pair it with culottes for a relaxed yet stylish touch.
Pick neutral colors for a classic look, or try a brighter shade if you’re feeling bold. Complete this style with loafers or ankle boots.
Add simple jewelry to keep it fresh and easy.
8. Denim jacket layered over a striped tee and chinos
A denim jacket adds a classic touch to your outfit. Pair it with a striped tee for a simple, timeless look.
Chinos offer comfort and a bit of structure that works well for fall. Wear neutral or earth-tone chinos for a relaxed feel.
Finish with comfortable sneakers or flats.
9. Cozy oversized scarf combined with a sweater dress
A cozy oversized scarf with a sweater dress is a simple way to stay warm as the weather cools. Drape the scarf around your neck or shoulders for extra comfort.
This combo works well with boots or favorite flats. Pick neutral colors or gentle patterns to keep dressing easy and stylish.
10. Suede ankle boots with high-rise mom jeans
Pair suede ankle boots with high-rise mom jeans for a classic and comfortable fall look. The high-rise jeans flatter your waist and create a clean line.
Choose boots in tan, brown, or black to match the season. Add a simple sweater or blouse for a relaxed but stylish finish.
This outfit fits daily errands or casual get-togethers.
11. Fitted mock neck top under a sleeveless vest
Layer a fitted mock neck top under a sleeveless vest for a clean, modern look. The high neckline adds warmth and style for fall.
The vest creates structure and interest. Pair this combo with relaxed jeans or straight-leg pants.
Add loafers or ankle boots to complete your outfit.
12. Neutral-toned trench coat with slim trousers
A neutral-toned trench coat pairs easily with slim trousers. This look feels polished yet simple for fall days.
Wear your trench open over a light sweater. Pick trousers in black, tan, or gray for a timeless match.
Add ankle boots for extra style and comfort. Stick to solid colors and classic cuts for a fresh, modern look.
13. Plaid skirt paired with a cable-knit sweater
A plaid skirt and a cable-knit sweater make a timeless fall outfit. This look fits casual days, shopping, or lunch with friends.
Choose a knee-length plaid skirt for comfort. Pair it with a classic cable-knit sweater in a neutral or soft color.
Finish with ankle boots or flats for a relaxed, polished style.
14. Slip dress layered over a long-sleeve tee
Switch up your fall wardrobe by wearing a slip dress over a long-sleeve tee. This pairing gives you an easy way to look stylish and stay warm.
Try a simple, solid tee under a patterned or colored slip dress for a balanced look. Wear boots or sneakers to keep it casual and comfortable.
15. Chunky leather belt accentuating an A-line skirt
Try adding some shape to your fall outfit by pairing a chunky leather belt with an A-line skirt. The belt defines your waist and gives your look more structure.
An A-line skirt feels flattering and comfortable, especially for women over 40. A thicker belt draws attention to your midsection in a classic, stylish way.
