Cozy Outfits to Wear on Repeat This Fall

When thinking about the outfits that we’re going to wear over and over in the fall, it’s the staple pieces that are comfortable enough to go out running errands, go to work, and maybe go out to dinner with friends. They don’t make sense in just one situation, but many.

Keeping in mind that these pieces will see a lot of wear throughout the season, quality is important. Quality material and quality fabrication. You should be excited to put these things on at the beginning of the season and just as excited at the end.

1. Camel Coat, Cream Turtleneck, and Straight Jeans

The wool camel coat is definitely making the biggest statement in this outfit, while the base of the cream sweater and the straight jeans looks chic and put together without saying too much. I like that this outfit could be changed in many ways with the type of shoe that you choose to wear. A sneaker would make it more casual. A ballet flat would make it more feminine. A riding boot would add a little bit more flair to the silhouette.

Neutrals are a good way to go. The camel and the cream together are easy to throw on and look chic, while the straight jeans keep it from being an all-neutral outfit.

2. Chunky Cardigan, White Tee, and Corduroy Pants

Corduroy pants in this burnt orange color are always going to make sense in fall. We again have the neutrals on top that are easy to throw on. A clean white tee like this makes the outfit feel cozy but still put together because of how crisp it is. The chunky cardigan is warm but also gives you a little bit more coverage.

I like that she’s wearing clogs here. It feels very fall to wear clogs. I also like clogs with a slightly more fitted leg, so she could wear this with straight jeans too.

3. Plaid Blazer, Fine-Knit Sweater, and Dark Denim

Dark denim with a straight cut like this, with a loafer and a little blazer, is classic academia aesthetic. Again, we have the cream sweater with the denim. Very easy to put together, very easy to throw on.

She has a little leather bag that matches her loafers. I could also see that being an oversized tote bag, maybe in a suede or a canvas. A big utility bag would look cute here.

4. Sweater Dress, Tall Boots, and a Long Coat

A sweater dress is such a forgiving, cozy piece to have in your closet. It’s so easy to throw on, it doesn’t usually require much ironing, and you don’t have to think too much about the layers underneath because it’s warm enough on its own. Here she threw on a long wool coat, which always elevates an outfit, as we’ve seen before.

I love a boot underneath a skirt or a dress for fall, especially a tall boot like this with a midi length. While skirts and boots go together no matter the length of the skirt, I do find that a midi length is easier to move around in because there’s less volume.

5. Denim Jacket, Hoodie, and Black Leggings

A hoodie is a very comfortable base piece to have on. Throw the collared jacket on top, whether it’s a denim like this, a wool blazer, or a long wool jacket, and the hoodie and the collar look really good together.

The leggings and the clean white sneakers feel like clean girl while still being cozy and put together. The denim jacket is definitely what’s lifting this otherwise athletic workout outfit from athletic to casual errand.

6. Cable-Knit Sweater, Satin Skirt, and Ankle Boots

Here’s a midi length skirt combined with ankle boots. She could keep her legs bare underneath the midi skirt, or add a sheer tight, which would look good. Sometimes if you do need a sheer tight because the weather is colder, the ankle boot might look better in something a little bit darker so that the colors don’t contrast too much.

If you want to add a little bit more warmth, you could also go with a thicker tight. In that situation, I think taller boots that hide the tight completely could look good. If you’re wearing taller boots, they don’t necessarily need to be darker. She could have something like this and not have to worry about the color of the tight, especially with the cream sweater and the lighter colored skirt on top. Something that’s light on the bottom could also look good.

7. Quilted Vest, Striped Tee, and Wide-Leg Jeans

I like the wide leg jeans in this fit. Recently we’ve been seeing a lot of baggier wide leg jeans, but this is a good option if you’re looking for more of a mid-rise rather than a low waist.

The quilted vest is a subtle statement here. It definitely adds warmth, but it’s not as thick as the puffer vest that we more often see. I like that the striped tee is striped in the same color as the quilted vest. It looks like a subtle intentionality. The shoes are also a good color combination with the green that she has going on top, and it combines nicely with the neutral bag.

8. Striped Sweater, Olive Jacket, and Cream Denim

I love a cream denim in a thick material like this. Cream or light colored denim should always be thick and not see-through. Here it’s more fitted, but it still works because of the material.

The suede beige boots pop against the darker leather bag. Suede and leather sometimes feel like they might not go together, but when the colors are similar, they do. The green utility jacket makes this outfit feel more like fall. If she didn’t have a jacket or a sweater, it might feel more like a summer outfit.

9. Knit Polo, Pleated Pants, and Sneakers

The polo and the pleated pants feel more corporate while being easy to throw on. It still feels professional. What brings this outfit more casual is definitely the sneakers.

Rather than going to work, she could be walking around the city, going to a museum, or going to lunch. It feels preppy, but not necessarily like workwear.

10. Fair Isle Sweater, Ecru Jeans, and Chelsea Boots

Again, here we have the light colored jeans making the statement. We can wear light denim after Labor Day. This is a very cozy fall outfit that definitely makes sense.

The light colors in the Fair Isle sweater match seamlessly with the light jeans. I like that she has combined the almost workwear boots with the brown leather belt.

11. Leather Jacket, Cashmere Crewneck, and Midi Skirt

Here we have a midi skirt that’s not satin or silk like we often see with the midi skirt. I like that this one is in a thicker, more hardworking fabric, so it can be a little bit more fitted. With a satin or silk, you have to be wary not to have it too tight, because there’s not much give, whereas something with elastic can be a little bit tighter.

A midi skirt like this is great. We could also have a classic pencil length, which would look good with this same combination of pieces.

12. Oversized Scarf, Peacoat, and Vintage-Wash Jeans

An oversized scarf is a classic combination with a peacoat. I love a peacoat, especially in this length. It’s not long like a long wool coat, and it’s not short like a puffer jacket, so you definitely have use for it.

A puffer jacket would make this outfit much more casual, but there are times when you don’t want a full long coat but you want to look just as polished, and that’s where the peacoat comes in.

13. Turtleneck, Slip Dress, and Tall Boots

I love a camisole or just a strappy top layered over a turtleneck, especially black. I think a black turtleneck is the most subtle option. She could also do a white turtleneck here, but black is definitely more of a going out color.

Brown and black together go great. The heeled boots underneath the bias cut midi dress is a great silhouette.

14. Flannel Shirt, Puffer Vest, and Slim Jeans

It’s not my first inclination to layer a flannel with a puffer vest. I often think about athletic materials together and more polished materials together, but combining the synthetic and the natural fibers like this is a really great attention to detail.

She has thick wool socks that are super cozy popping out of hardworking work boots. The skinny jeans make the outfit feel a little bit more feminine than if she were wearing a looser fit jean.

15. Bouclé Jacket, Knit Top, and Relaxed Jeans

This is a little bit more of a feminine silhouette, with the curve of her collar and the cut of the jacket combined with the ballet flats. I don’t often see ballet flats in a nude like this, but it gives a little bit more of a subtle touch than the brighter colors we often see.

The jeans are more relaxed, which adds a little bit of definition to the outfit, rather than if she were to go with a skirt or something with less structure.

16. Brown Suede Jacket, Cream Sweater, and Black Denim

Black denim and brown suede go so well together. It’s such a timeless combination. A cream sweater is a good addition, and the cream here definitely keeps the outfit lighter.

She could definitely wear a black shirt under here too, to really accentuate the brown suede with the black.

17. Wrap Coat, Cashmere Scarf, and Black Column Base

Here’s a little bit more subtle of a contrast than we’ve seen above. The wrap coat and cashmere scarf are neutrals that feel almost alike, but not completely, over a black column base.

The black column base can really be whatever combination you’d like. It could be denim, it could be trousers combined with a turtleneck, even a black hoodie. It looks chic to have a black column base, and then you can throw the two neutrals on top and it all goes well together.

18. Trench Coat, Hoodie, and Wide-Leg Trousers

Here’s the collared jacket with the hoodie that we love. The trench coat definitely makes sense, especially in this rainy fall weather.

I like that she has the white sneakers combined with the black and brown on top. It gives it a little bit more pop and polish than if she were to have a black sneaker, which would kind of make the outfit more forgettable.

19. Burgundy Sweater, Plaid Trousers, and Loafers

I love a subtle pattern like the plaid that we’re seeing in these trousers. It’s almost not noticeable, but it definitely adds a little bit of interest to the outfit. The burgundy sweater is such a rich color, and it accentuates the pop of burgundy that we see in the plaid.

Plaid is a cozy fall pattern, and here it is toned down into something more academic, close to workwear, while still feeling warm and comfortable.

20. Fleece Pullover, Utility Pants, and Trail Sneakers

Trail sneakers that are neither a boot nor an actual sneaker have become more and more trendy as of late. They definitely make sense in this situation where she’s actually on the trail, but we see trail sneakers even in streetwear these days. Utility pants are a good combination with the sneaker. Whether or not you’re actually outdoors, they look like they make sense together.

She could wear a leisure pullover like this, or even just a t-shirt with a denim jacket, or a leather jacket if it were a little bit more polished than a hiking trail.

21. Denim Shirt, Wool Skirt, and Knee Boots

A wool skirt is a cozy statement piece that doesn’t take as much thought as we may think. I love the knee-high boot that she has here, which makes sense with the brown leather accents.

Suede and leather go naturally together with denim like the shirt she has on. Another option would be a plain white t-shirt, a cream turtleneck, or a cream sweater.

22. Puffer Coat, Knit Set, and Waterproof Boots

A knit set in a neutral like this is always elegant and chic. It feels like high-class leisure wear that doesn’t feel slumpy in any way. Here she has the puffer coat on top, maximizing coziness. This is the fluffiest puffer, and with a puffer, really no matter the length, the bigger the better. Unless you really want something low-key, I think a puffer should be as big as you can handle it.

Waterproof boots like this are a great practical option, since they’re not really leather and more of a synthetic material that’s waterproof. The leather bag makes sense, and its neutral color matches the set. If she didn’t need a waterproof boot per se, a white sneaker could make sense.

She could also go full neutral with the white sneaker and a trench coat on top. The knit set is definitely maximum coziness that can be played up or played down.

Pieces That Pull These Looks Together

Three classics that make these cozy outfits look put together.

• Steve Madden Double-Breasted Trench Coat. The trench in #18, easy to wear over a hoodie or a fine knit.
• CUSHIONAIRE Leather Penny Loafers. Sharpens up the knit polo in #9 and the burgundy sweater in #19.
• PUMA Carina Leather Sneaker. A clean white sneaker for the quilted vest in #7 and the denim jacket and hoodie in #5.