Warm Fall Outfits Built for Cold Autumn Weather

Warm fall outfits can be very simple to put together. The key is that layers matter, and each layer should keep what you’re wearing comfortable throughout the day as the temperature changes, and be easy to carry around if you end up removing layers.

Each layer, and each combination of layers, should be cute and presentable on its own, no matter what you’re wearing.

1. A Chunky Knit Sweater, Straight-Leg Jeans, and Chelsea Boots

A sweater and pants combination with boots is a fall classic, one of the easiest combinations to put together. A sweater is so warm that often you don’t need a jacket on top. In early fall, or when the temperature rises during the afternoon, you might find yourself warm enough to take off the sweater, so it’s important to make sure what’s underneath is a layer that will still keep you warm enough while staying presentable.

2. An Oversized Cardigan, a White Tee, and Leggings

I love an oversized cardigan, especially a long one like this that goes down past the knee. It feels really 90s Rachel Green. Leggings and a white t-shirt are nice here because they look basic enough to not pull the eye away from the statement piece, the oversized cardigan.

A lot of people have leggings and a t-shirt in their closet already, and you can swap out the shirt for a different color depending on the color of the cardigan. It should coordinate fairly easily. It’s also nice because the cardigan is really warm, and a t-shirt underneath still looks good if you have to take the cardigan off.

3. A Trench Coat, a Turtleneck, and Tailored Trousers

A beige trench coat like this is a great addition to really any wardrobe because it looks good in any season. The beige goes well with most colors, so it’s a great piece to have in any capsule wardrobe.

The outfit here looks more interesting because of the gray trousers with the other warm neutrals, and the matching brown loafers and brown bag keep it cohesive. Loafers are a great fall shoe. They almost look academic, like you’re on a college campus.

4. A Plaid Flannel Shirt, a Cami, and Skinny Jeans

Skinny jeans are definitely coming back, and this is a classic way to wear them, especially flat with an ankle boot. The point on the ankle boot makes it look a little more modern, which is important with skinny jeans so it doesn’t feel too 2016. A cami is nice because it looks really good with or without the flannel, and a flannel definitely keeps you warm, sometimes too warm, so it’s nice to be able to keep it open.

5. A Sweater Dress, Knee-High Boots, and Tights

I love a sweater dress. I think it’s so flattering, and it’s not like other bodycon dresses because the knit is more forgiving, especially ribbed like this. This length that hits right below the knee is very flattering, especially with the calf-high boots.

It can be a little hard to know what to do with that small area above the boot and below the dress, but here it looks good with the dark black tights, which also make the outfit warmer. She has a charcoal jacket that helps pull in the black. Coordinating the tights can be tricky depending on the other accessories, but this works as long as the boots and bag are cohesive, so it doesn’t feel like too many colors are happening at once.

6. A Puffer Vest, a Long-Sleeve Tee, and Joggers

This is definitely athleisure, but it still looks put together and intentional. This is the first beanie we’ve seen, and a beanie is a great accessory for any fall outfit. Here it’s more leisurely, but it can be worn with more polished or professional outfits too.

A puffer jacket or puffer vest is great because they keep you surprisingly warm. Here she’s just wearing a t-shirt underneath, but puffer vests are usually pretty good at keeping the heat on your core.

7. A Plaid Blazer, a Mock Neck, and Dark Denim

Mock neck shirts are great in fall and winter. If you feel good in a mock neck, it’s a great piece to have in your closet because it just looks a little more sophisticated and intentional, a little more professional, especially here with the blazer and the loafers.

This looks like a professional outfit even though she’s wearing jeans. Dark denim is obviously more professional-leaning than anything lighter. Black denim could also work, but dark denim is almost a little more professional than black denim, because black denim is a little easier to fade, which gives it a less professional look.

8. A Cable-Knit Turtleneck, a Corduroy Midi Skirt, and Tall Boots

Midi skirts are so great. Rather than the satin or silk ones you see in the summer, the fall version should be a little less flowy, letting in less air. Here it’s corduroy, which is more wind-breaking than silk or satin. Suede works great too.

I actually feel like I don’t see a lot of leather midi skirts. We definitely see leather mini skirts, but not many midi versions. Corduroy, suede, or even denim is a great option for a fall skirt. The boot is hidden under the length here, which is easier to work with than a shorter skirt, since a mini skirt and tall boots is a more classic, easy combination.

9. A Denim Jacket Over a Hoodie with Corduroy Pants

Starting from the top, a hoodie underneath a collared jacket almost always looks good. Here it’s a real hoodie, but you could also do a zip-up hoodie underneath a jacket like this. Denim is a good choice, but really any collared jacket looks good with a hoodie, and a hoodie underneath anything is a good way to layer in the fall. You could even put a t-shirt over a hoodie and it would look good.

These are great corduroy straight-leg pants, a good cut that’s not flared and not skinny. It looks casual but still tailored and fitted. We also have the Converse, which I feel like I’m seeing a little more of. They’re not necessarily trendy, but they never go out of style.

10. A Shacket, a Ribbed Tank, and Wide-Leg Jeans

Starting from the bottom, the wide jeans look great with a heel like this. It makes the leg look much longer and is a change from the usual wide baggy jean with sneakers. The boot makes the outfit look more polished.

She has a ribbed tank underneath, which is a little more interesting than a basic cami that might be our first inclination to grab. Then a shacket is a good oversized option that adds more warmth than an actual shirt would, and it looks a little more ready to leave the house than just having an open shirt.

11. A Wool Coat, a Cashmere Sweater, and Loafers

This is definitely a warm outfit with the wool coat and cashmere sweater, and it’s a great example of how to layer in the fall, winter, and shoulder seasons. She has a wool coat on the outside that’s a thicker weave, blocking the wind, and it even has a collar you can see she’s pulling up. The cashmere is a good insulating middle layer creating warmth, and she probably has a base layer underneath that traps air and wicks away moisture.

The taupe trousers are a great color that transitions between the dark loafers and the cooler colors on top. Taupe is a really great color, and I think it always adds to outfits that use it.

12. A Fair Isle Sweater, Leggings, and Duck Boots

A fair isle sweater feels a little European and is definitely really warm. You can see why she’s not wearing a jacket here. If it’s raining, it’s probably not that cold outside, so a fair isle sweater and a hat will probably do it.

Duck boots and leggings look good together, and it’s a good excuse to have a thick sock popping out of the duck boots rather than a no-show sock. A leg warmer would look good too. Duck boots are great because they’re waterproof and feel a little more outdoorsy, almost a Southern style, but really anyone can wear them. They’re useful and have a real purpose in fall weather.

13. A Leather Jacket, a Striped Tee, and Mom Jeans

This is a very classic, simple outfit. You could change up the color of any of the leather accessories, like the jacket, the boots, or the bag, and it would still make sense, or change the color of the shirt to add a different pattern.

What’s important to note here is that she rolled up the hem of her jeans. With an ankle boot like this, you’d want to either roll it up or let it all the way down. If it’s just sitting at the top of the boot, it’s not really flattering. You should either see some ankle or see no ankle, not just a little peek every once in a while.

14. A Wool Cape, Skinny Jeans, and Ankle Boots

This is a great cape example, and capes are definitely in. I personally find it hard to find a cape, and hard to find an outfit that goes with one, but it almost always makes sense when I see someone wearing a cape. It’s just not the first thing I grab.

This works because of the brown and the black gray tones. Brown and black is a really underused color combination. There’s not much going on here in a distracting way except for the statement piece being the cape, but it doesn’t look like too much is happening. It’s flattering without looking eccentric, even though she’s wearing a cape.

15. A Quilted Jacket, a Cowl-Neck Sweater, and Cords

Here she’s wearing calf-length boots with the corduroys tucked in, which is a nice option with looser boots like that. It definitely looks like a fall, almost horseback-riding outfit, especially with the quilted jacket.

The scarf and the sweater underneath are great staples to have. A cream sweater is nice in any capsule wardrobe, and a plaid scarf can go with almost any fall outfit. The horseback-riding theme is a good one to lean into in the fall.

16. A Matching Knit Set: A Cardigan and Trousers

This is so cute being all knit, and the colors are almost exactly the same, which is important if you’re going for one cohesive look. If it were a knit trouser you couldn’t really wear it to work, but this looks like it’s wool or a woven wool, which has pockets and is a little more professional. The matching cardigan pulls the outfit together.

17. A Sherpa Pullover, a Henley, and Leggings

Henleys are kind of underused. They feel a little leisurely, but they’re always flattering for men or women. This whole outfit is a good athleisure example. The sherpa pullover is so cozy, and the shoes, which are almost hiking-boot sneakers, are a little more substantial and interesting compared with the basics on top, which is nice.

18. A Turtleneck Under a Slip Dress with Boots

A black turtleneck is a great option in the winter, and it’s also a great way to layer. Any time you have a camisole over a turtleneck or a t-shirt, I think it looks good, and it’s a little nod to the 90s.

The black boots go well with this outfit, and it’s nice to pair a black boot with a sheer black tight like she’s wearing. Like we said before, it’s hard to know what to do with that one inch of skin that shows, but a black boot fades easily into the sheer black tight. She could wear the belt here, which she is, though I think it would also look good without one.

The beige jacket actually makes sense with this outfit. At first you might think she’d choose a darker jacket, but wearing something lighter lightens up the whole outfit rather than throwing another dark layer on top of an already dark outfit. With the jacket, everything looks more interesting.

19. A Corduroy Blazer, a Sweater, and Straight Jeans

This blazer is not oversized, but it’s definitely big enough to fit a sweater underneath. That’s something to keep in mind if you’re looking for a blazer to throw over a fall or winter outfit, maybe go a size up because you’ll be putting sweaters underneath.

The sweater here is again a cream sweater, which is a good staple to have. It’s almost second nature to reach for darker colors in fall and winter, but a cream top makes the whole outfit feel lighter. If you reach for a black shirt, then you’d be looking for black shoes and a black bag, so this keeps everything lighter.

20. A Blanket Scarf, a Sweater, Jeans, and Booties

Here the warmth is coming from her huge, cozy blanket scarf. A blanket scarf is great because it really does keep you warm, and depending on how wide it is, you could also wear it more like a shawl. If you’re sitting in a cafe, it could keep you warm on your lap.

We have another cream sweater and brown boots. The brown boots and brown bag combination is nice. Black boots are good for going out, but it’s good to have a lighter option during the day, and the boots set the foundation of the whole outfit.

21. A Cropped Sweater, High-Rise Trousers, and Loafers

Again she has brown loafers, adding richness in color to an otherwise cooler outfit. It’s nice that the sweater is cropped, because tucking a sweater into trousers isn’t always a given, it can be a little too much fabric to tuck in.

Tucking in your top is flattering, and I think that’s why a lot of millennials have the inclination to tuck in the front, but it can be a little repetitive. Having something cropped at the waist like this, without actually having to tuck in, is the best of both worlds.

22. A Long Cardigan Duster, a Bodysuit, and Jeans

Here’s another long cardigan without buttons, with a full black base underneath, meaning a black top, dark or black jeans, and black boots. That always looks good, and you can throw almost any color on top of it. Here it’s a brown and beige, and brown and black look really good together, kind of an underused color combination. This could work with another jacket or cardigan on top too, maybe even a statement piece that gets toned down by the full black base.

23. A Sweater Vest, a Collared Shirt, and Wide Jeans

This is another good example of how to keep the core warm while having lighter layers underneath. A collared shirt under a sweater vest is really academic, and it pairs well with the little loafers she has on. The wide jeans make it more casual and not necessarily a work outfit.

This could be worn to class or just out running errands. It doesn’t feel too stuffy. A sweater vest isn’t quite a year-round staple, but it’s a great thing to have in your closet because it layers pretty easily.

24. A Faux-Fur Collar Coat, a Knit Dress, and Boots

I really like the colors going on here. The chocolate brown and the black give variety without popping too much. The pop is definitely coming from the faux fur collar, which feels sophisticated and polished but also a little exciting and fashionable, over a flattering midi knit dress underneath.

25. A Henley, Denim Overalls, and Ankle Boots

Here’s another henley, casual and comfortable, with overalls. Overalls are great. They’re more casual than regular denim and can’t be worn in every situation, but this is a great way to wear them. She looks like she’s gardening or out at a pumpkin patch, which is a great situation for overalls. When you do wear them they’re really cute, though finding the opportunity can be a little harder. Fall, or summer, is definitely the season to do it.

26. A Mock-Neck Bodysuit, Faux-Leather Leggings, and Boots

The faux leather leggings and the boots look really cool together because it looks like an almost seamless transition, which makes her legs look really long. The leather adds interest to an outfit that would otherwise be all the same, since it’s all black.

We’ve seen this before with black denim, but here it actually looks better with the leather leggings and leather boots than black denim would. This is a great way to wear all black while still having an interesting outfit.

27. A Utility Jacket, a Turtleneck, and Cargo Pants

This whole outfit is pretty utility. We have the cargo pants and the combat boots, which are heeled, so it’s a little more feminine than if they were flat. Then there’s the utility jacket in a khaki green, with a cream cardigan and light turtleneck underneath. Going with a light cardigan or light turtleneck underneath is a good choice here.

28. An Elevated Sweat Set with Clean Sneakers

This is a great warm and comfortable option that’s easy to put together, a matching hoodie and joggers. It’s nice that the hoodie and joggers are coordinating colors, a rich warm color underneath a toned jacket that’s long and slightly wind-breaking with a thicker wool to keep you warm.

We also have the hood underneath the collar, which is a good combination of polished and casual. Those two contradicting collars make for an interesting outfit on top.

29. A Cropped Puffer, a Turtleneck, and Straight-Leg Jeans

Puffer jackets are so good in fall and winter. In winter I often think of a huge puffer jacket, where the bigger the better, but in the fall it really doesn’t make sense to have a huge one, so a cropped puffer is a good compromise. You can wear a cropped puffer into winter too, as long as you go longer or thicker underneath. Again we have the cream turtleneck, which keeps the outfit light.

30. A Camel Coat, a Black Turtleneck, and Tall Boots

Here we have the brown, beige, and black color combination, which is an easy one to reach for. The all-black underneath, with a long boot and the long beige coat, is a simple outfit to put together. The black pants and black shirt are easy to reach for, and they pull in the black leather gloves she’s wearing, while the brown leather of the coat matches the brown leather of the bag.

Warm outfits usually mean wool. Woolmark’s washing guide recommends a wool or delicates cycle and drying flat in the shade, and its pilling guide suggests a fabric shaver for the pills that build up on heavily worn sweaters.

What to Shop for These Outfits

Three pieces that work with several outfits on this list.

• CUSHIONAIRE Leather Penny Loafers. The loafers that finish the wool coat and cashmere sweater in #11.
• PUMA Carina Leather Sneaker. The clean sneaker for the elevated sweat set in #28.
• befen Genuine Leather Tote Bag. A cognac bag that matches the camel coat in #30 and the corduroy blazer in #19.