Casual Winter Outfit Ideas

As we slog through this loooong month of January, I thought I’d round up some casual winter outfits to help inspire you to shop your closet for new ideas. Maybe you’ll even find one or two things you want to add to your wardrobe to get you through the rest of the season!

SIZING NOTES: I’m 5’5″ and I usually wear a small in tops, a 28 or 29 in jeans, and a size 8 shoe. Gifted items are indicated by c/o; everything else I purchased myself.

20 Casual Winter Outfit Ideas

#1. I love this leveled-up look with washed black flares, camel cocoon coat, and plaid scarf.

scarf // similar coat (6) // jeans (29; option) // boots (8; option)

Underneath, I’m wearing my favorite Equipment cashmere v-neck sweater in camel.

sweater (S; option/option) // jeans (29; option) // boots (8; option) // bag (option)

#2. I’ve shared this outfit a lot this winter, but it’s one of my favorites. So simple, but the plaid scarf and oversized sunnies really amp up the style factor, and I linked similar options for less.

similar coat // scarf (option) // sweater (S; option) // similar jeans (29; option) // boots (8.5; option) // similar bag // similar sunnies // earrings (option)

Underneath, I’m wearing the Jenni Kayne ivory fisherman sweater, and Quince has a similar version for less.

sweater (S; option) // similar jeans (29; option) // boots (8.5; option)

Here’s how it looks with bootcut jeans and more of a Western style bootie.

sweater (S; option) // jeans (29; option) // booties (8)

#3. And this is a more affordable version of pretty much the same outfit, from Gap Factory.

sweater in Birch (S) // jeans (29) // booties (8)

#4. This layered look with black pants is a favorite from last year. If it’s too cold for a denim jacket where you live, you could definitely swap it out for a wool coat.

scarf // denim jacket (S) // similar sweater (S) // pants (M; option) // sneakers (39) // bag (option)

#5. And here’s another layered look I’ve always loved. I’d just swap out the skinnies for straight ankle jeans.

scarf // similar coat // sweater (option) // jeans (option) // sneakers (39; boot option) // sunnies

#6. Don’t forget about your white jeans when styling winter outfits! If you put them away for fall, this is a great time to pull them out again. They pair perfectly with winter brights for a fresh and unexpectedly chic look this time of year.

sweater (S) // jeans (29; option) // boots (option) // similar earrings // bag (option)

#7. Here’s an easy outfit with bootcut jeans and a bold sweater. I love the colorful stripes grounded on this black rib knit sweater, and I chose black boots to bookend the look.

sweater (S) // jeans (29; option) // boots (8; option) // sunnies (option) // bag (option)

#8. This outfit may not look very wintry, but it’s a good one for those in the south with milder winter weather. I often wear this around the house. My embroidered sweatshirt sold out, so I linked a similar one.

sweatshirt (S; option) // jeans (28; option) // similar sneakers (39)

#9. Here’s another look with an elevated sweatshirt of sorts. It’s more of a thermal, but anyway! I love this bright pink, and the light wash straight leg jeans over black lug sole Chelsea boots is very much on trend right now.

thermal (S) // jeans (29; option) // boots (8; option) // earrings (option)

#10. And this is an easy one to recreate… just layer on all the black! Bonus points for a mix of textures for added interest.

similar leather bombers // t-shirt (sweater option/option) // similar jeans (28; option) // belt // similar shoes

#11. This is pretty much the same outfit with a camel sweater underneath. If it’s too cold where you are for mules, you could swap them out for boots.

similar leather bombers // sweater (S; option/option) // similar jeans (28; option) // shoes (8)

#12. I also love a grey sweater with denim and a black leather jacket on top.

sweater (S; option) // similar jeans (29; option) // sneakers (39) // similar leather jackets

#13. I do black and grey a lot in the wintertime… Here’s a similar look with black jeans instead of blue.

turtleneck (S; option) // similar jeans // similar sneakers // similar leather jackets // earrings // bag

And this time, I wore a vest rather than a leather jacket.

similar turtleneck (S) // similar vest // similar jeans // sneakers (39) // tote // sunnies

#14. If you’re tired of all the neutrals, pink is a huge trend this winter. This cozy sweater is a splurge, but I found a similar option for less.

sweater (S; option) // jeans (29; option) // boots (8) // earrings // sunnies (option)

#15. And this cashmere boatneck sweater is one of my favorites. I have the merlot and the peacock blue. The merlot sold out, but I love that berry color.

sweater // jeans (28; option) // similar bootie // bag (option) // earrings (option)

#16. And here’s a similar look with the peacock blue.

sweater // jeans (28; option) // booties in Cloud Suede (8) // earrings

Here’s the same look leveled a bit for a dinner out.

sweater // jeans (28; option) // booties (8) // boucle coat (S) // similar earrings // similar bag

#17. Sometimes I wear this sweater with medium to light wash blue jeans; in this case, I usually wear a lighter bootie.

sweater // jeans (29; option) // booties in Cloud Suede (8) // earrings

#18. Outerwear can really make or break and outfit; I love a plaid coat over a neutral combo like this oatmeal sweater and grey jeans. I’d swap the mules for boots to make this more winter-appropriate.

similar coats // similar sweater (S) // similar jeans (28) // mules (7.5; boot option) // bag // sunnies (option)

#19. Or a teddy coat is a trendy option. I love this camel color over an all black outfit.

teddy coat (S) // similar sweater (S) // jeans (29) // boots (8) // bag (option) // sunnies (option)

#20. I also like this brown faux leather moto over a neutral outfit. The sneakers provide a fun juxtaposition, but you can also wear booties.

jacket (S) // similar sweater (S) // similar jeans // similar sneakers // sunnies  // earrings // similar tote // similar belt

#21. When you want to keep it casual joggers are always a good option. This is another outfit that is better suited for milder winters… I wouldn’t be wearing this with snow on the ground, but we get some mild winter days here in Philly.

sherpa (S) // joggers (M) // top (M) // sneakers (8.5)

#22. And I shared this just recently, but it’s a fun casual look that will carry you into spring.

top (S) // jeans (29; option) // boots (8) // bag // sunnies (option)

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26 Responses

  1. So many great looks. I did notice you did not include the Kut from the Kloth brown raw hem coated jeans. I bought them after you showed them in the fall and have been wearing them a lot. Hope they aren’t out of style. I always look forward to your posts.

  2. I love love all the outfits and they are doable and I should say, I was inspired by you. I decided to dress up to go out with the girls on Monday. It felt so good and I did some nice dark blue jeans, with a sweater and ankle boots. And I accessorized with a long chain 🙂 Its been hard to be motivated to dress up (even the basic outfit) after being stuck at home, then being full time remote. Thank you for the inspiration and I can relate to your style of being elegant and simple and chic. 🙂

  3. I like the Caslon drape neck sweatshirt– is it pink or lavender? It looks lavender in your photos but says pink on the site. Also, I am still looking for a pair of black boots with a 7.5″ ish shaft and a 2-inch heel. A unicorn! Any ideas? I wear between a 10 and an 11 which makes the whole issue harder. lol. The Tory Burch boots you featured were perfect, but alas I received 2 different-sized boots in my box and now they are sold out. 🙁 I have found a few pairs with a western style heel but I don’t love that look. I am looking for a boot I can wear with jeans as well as dressy pants to take on a 3-week trip to Europe for dressier occasions with jeans or slacks.

    1. Colleen, I have 2inch pointed toe boots from Clark’s. I have a black leather and a camel suede. They call it Teresa. You can find them on Clark’s website and DSW. They might be cheaper at DSW. They are real comfortable and look great dressed up or casual. I’m not sure of the shaft but they are higher than ankle. I love them with my bootleg jeans and pants. Pointed toe boots were a no no for me until I discovered Clark’s makes comfortable stylish pointed toe shoes and boots. I have several of both. Hope this helps.

    2. Hey Colleen, I would call it somewhere in between – definitely leans lavender. For the boots, that’s a tall order! I would see what you can find in Blondo boots – they tend to check all those boxes. Sizes just seem to be picked over this time of year.

  4. What a great post! Lots of great ideas. Flares look so good on you! I love them too–never thought I would but now I have 2 pairs. And I have 2 leather jackets…but never thought to wear them with sneakers. So now I will! Thanks!

  5. Hi Jo-Lynne!! You have some amazing outfits. My favorite is #1. You look fantastic in all of them. Hope you have a Great Day!!
    Linda W.💐

  6. Have you ever had an issue with your dark denim jeans rubbing off on your light colored suede booties? I have the Dolce Vita western style booties and I want to wear them like you did in #16, but I’m so scared my dark jeans will ruin them!

    1. MMASC……. I have had this problem a lot. I have had several light suede booties over the years and they’ve been ruined from denim. I have learned not to have the denim touching them, but this is hard with the styles changing on denim and if you don’t like the rolled look anymore. Crop straight work pretty good. Its annoying and as much as I love suede, I haven’t bought any the last 2 yrs. due to this problem.

      1. Kathy-thank you! This is exactly what I’m afraid of. I LOVE the Dolce Vita boots, but all of the jeans I want to wear them with aren’t light AND they’re boot cut, so will definitely touch. 🙁

    2. Hm, I didn’t wear the black jeans with those Marc Fisher boots for long. I usually wear light boots with light wash jeans. The Dolce Vita booties in Dune and Marc Fisher in Cloud Suede still look great – no denim transfer.

  7. I live in the rainy Pacific NW. A typical winter day is 40 degrees and drizzling. It’s difficult to find nice looking waterproof coats that are stylish. Wool, sherpa coats, etc tend to just get soggy and smell like wet wool. Could you potentially do a post on fashionable water resistant/proof stylish outerwear? Most of us natives do not carry umbrellas. Thank you!

  8. Great outfits! I love the one of you in the teddy coat and snow boots! Super cute! And it’s something I’d never wear in my neck-of-the-woods so I love seeing what the other people wear when it’s that cold outside. I feel like January has gone SO fast! I cannot believe next week is February 1st already! And February is always so short with only all the holidays (and my anniversary) 😊. For me, March is the longest month of the year; seems to drag on forever with no breaks.
    I was going to order your cute black w/stripes turtleneck from Evereve, but bought the white sweater with the stripe of green and navy around the scoop neckline and sleeves….it’s really cute and so incredibly soft. I just am not sure if it looks too “I’m ready to play tennis all day” or not. It’s featured in their Evereve TV reels and it looks cute on the salesperson but not sure how much I’ll wear it. Cannot decide!!

  9. Thank you for all the links. I’m refreshing my wardrobe.

    I hope in the future you think about doing seasonal capsule collections for your followers. Something that could be released on a certain day with shipping links for all must haves 🤗

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