Fall & Winter Outfit Ideas to Wear This Season

Fall is hands down my FAVORITE season to dress for! The second the weather starts cooling off, I’m ready for sweaters, denim, jackets, boots, cute flats and ALL the layers. I’ve already shared so many fall outfits this year, so I wanted to create one big post where you can easily find everything I’m wearing throughout the season.

Below, I’m rounding up all of my recent fall outfit ideas, from simple jeans-and-sweater combinations to dresses, skirts, jackets and outfits that are a little more dressed up. Whether you’re trying to figure out what to wear for an everyday fall outfit, dinner, date night, a fall trip or just need some inspiration to get out of a closet rut, hopefully you’ll find a look you want to recreate!

I’ll be updating this post throughout fall and into winter with new outfits as I wear them, so definitely bookmark this page and check back whenever you need outfit inspiration! Once the temperatures really start to drop, I’ll add plenty of winter outfits with coats, boots and fun cold-weather looks here, too.

Everything I’m wearing is linked underneath each photo, along with similar options whenever something is sold out!

plaid mini dress for fall 2026

plaid mini dress

Outfit on the left: cardigan, jeans, flats, hair clip, phone chain, and phone case
Outfit on the right: sweater, slip dress, boots, and baby blanket

jacket, jeans, sunglasses, earrings, and similar handbags here and here

Outfit on the left: off the shoulder sweater, jeans in medium wash, pendant necklace, and leather mules
Outfit on the right: cardigan, tank top, jeans, and similar handbag

white top and skirt free people set

top & skirt set

Outfit on the left: cable knit cardigan, red paisley bandana scarf, jeans in medium wash, and similar brown suede heels
Outfit on the right: cardigan, jeans in medium wash, sunglasses (budget-friendly option here), similar handbag here and here, and similar brown suede heels

lace camisole and shorts with a tan barn jacket and knee high suede boots for fall 2026

lace camisole, lace shorts, jacket, boots, similar handbags here and here, and necklaces here and here

Outfit on the left: trench coat, sweater, jeans, shoes, handbag, earrings, phone chain and phone case
Outfit on the right: striped sweater, denim shirt, jeans, phone chain and phone case

brown cardigan sweater layered over a white tank top and barrel jeans with brown flats for fall 2026

cardigan, tank top, jeans in light wash, flats, and sunglasses

Outfit on the left: top, jeans in medium wash, sunglasses, and similar brown suede heels
Outfit on the right: cardigan, jeans in light wash, flats, tote, and necklaces here and here

oversized sweater with oversized scarf and jeans for fall 2026

sweater, scarf (similar scarf), jeans, glasses, and shoes

Outfit on the left: dress, boots, and similar handbags here and here
Outfit on the right: cropped trench coat, lace shorts, and sunglasses

suede jacket with jeans, a phone case with tortoise phone chain, large earrings for fall 2026

jacket, jeans, earrings, similar handbags here and here, phone chain, and phone case

Outfit on the left: cropped trench, jeans, sunglasses, and handbag
Outfit on the right: cardigan, jeans, hat, similar handbag, and boots

cardigan, lace shorts, leather mules, and canvas tote

Outfit on the left: fleece pullover and jeans
Outfit on the right: belted dress and boots

scarf layered over a turtleneck, barrel jeans, and a woven handbag for fall 2026

scarf, turtleneck, sunglasses, jeans in light wash, earrings, hair clip, handbag, and sunglasses

Outfit on the left: dress, similar sweater, flats, and phone case
Outfit on the right: cropped trench coat, t-shirt, jeans, and necklace

barbour quilted cream jacket, white jeans, brown suede sneakers, suede woven handbag for a fall 2026 outfit

jacket, tank top, jeans, sneakers, sunglasses, earrings, and handbag

Outfit on the left: top, jeans in light wash, flats, and handbag
Outfit on the right: jacket, jeans, sunglasses, and handbag

polka dot skirt outfit with suede heels and white top, 2026 fall outfit inspo

sweater, skirt, sunglasses, similar brown suede heels, and similar handbags here and here

Outfit on the left: sweater, jeans, hat, sunglasses, and heels
Outfit on the right: cardigan, shorts, flats, sunglasses, and similar handbags here and here

I’ll keep updating this post with new fall and winter outfits as I wear them, so make sure to bookmark it and check back throughout the season! Hopefully having everything in one place makes getting dressed a little easier the next time you’re staring at your closet wondering what to wear haha.

And as always, if something is sold out, I’ll do my best to link a similar option! Let me know which look is your favorite so far!

Leave a Comment

36 Comments

  1. I live for your fall outfits! I can barely choose a favorite but I think the way you style a good cardigan and skinny jeans is probably my favorite because it is so easy to recreate yet you always look so well put together and polished!
    xx Janine
    https://walkinmysneaks.blogspot.com/?m=1

    9.25.18Reply
  2. Wow, the fall looks you share here are wonderful!
    xx from Bavaria/Germany, Rena
    http://www.dressedwithsoul.com

    9.25.18Reply
  3. Love that white tie top and green denim look! Happy Fall 🙂

    Amanda @ Cupcake N Dreams

    9.25.18Reply
  4. It is entirely too difficult to choose just one look! I love them all. You always have the best fall outfits!

    9.25.18Reply
  5. Zoe

    Oops! The links for the suede skirt and blanket skirt outfit do not work. I’ve been looking for a nice blanket scarf and that one looks super cute!

    9.25.18Reply
    • Lillie

      This is my favorite too! I am hoping she gets the links to work

      9.26.18Reply
  6. Laura Leigh

    The white top with green denim is definitely my favorite! Absolutely love it lady! I am so sorry about your luggage! I hope it makes it to you ASAP!

    xo Laura Leigh
    Louella Reese

    9.25.18Reply
  7. I love all of your outfits !
    https://thefrenchiestblog.wordpress.com

    9.25.18Reply
  8. Ellen

    I LOVE the tan cardigan with white tank and leggings – looks so easy, but together and classy at the same time. I’ve got to recreate this one!

    9.25.18Reply
  9. Girl you are so pretty and have the BEST outfits for every seasons!! Before I really was into blogging i’d ALWAYS see your outfit photos on Pinterest!
    XO, Katie | http://www.meshkomoments.com

    9.25.18Reply
  10. All of your outfits are always so cute! Do you have any favorite stores (besides Nordstrom! That’s a bit out of my price range usually, haha) that you could share?

    9.25.18Reply
  11. Julie

    How can we get link to suede skirt?

    9.25.18Reply
  12. Candice

    All are fantastic but my favorite would have to be the long tan sweater with white tank, black leggings and leopard heels. 🙂

    9.25.18Reply
  13. All of these outfits are absolutely gorgeous!!
    Xo, Kelsey
    http://www.bleuandwhit.blogspot.com

    9.25.18Reply
  14. I always love your fall looks – if only I was as in-shape as you are! (But I have a baby, so #momlife) And I can’t believe you took a 6 seater plane… did that once, NEVER will again hah!

    9.25.18Reply
  15. Cathy Bentley

    The white poncho outfit is when I discovered your blog. Have been following ever since. All your outfits are wonderful. Thanks always for showing us just a little glimmer into your life. It is very much appreciated.

    9.25.18Reply
  16. You always have the best fall style! Can’t wait to see what’s to come this fall on your blog!

    9.25.18Reply
  17. Always love your fall looks! <3

    BlondieintheCity.com

    9.26.18Reply
  18. Love your fall looks! They’re always so fun 🙂

    Anika | anikamay.co.uk

    9.26.18Reply
  19. Carol Moseley

    I love the last look the most! Gray and tan pairing is so chic for fall! Plus Winnie looks so cute, she almost matches!

    9.26.18Reply
  20. Your Fall outfits are always the best!

    http://www.rdsobsessions.com

    9.26.18Reply
  21. LOVE that first dress!!!
    http://www.BubbleBathandBlossom.com

    9.26.18Reply
  22. Obsessing over these fall looks! Your style is so chic yet effortless. Your outfits are my inspiration.

    9.26.18Reply
  23. Christina Ollre

    First of all, love be your blog and second, geez I hope the whole luggage thing works out for y’all.

    Question- do you think riding boots are going out of style this year?

    9.26.18Reply
    • I don’t think riding boots are quite as “trendy” this year but they are definitely not out of style! Especially if you like more classic looks 🙂

      9.26.18Reply
  24. Gaelle

    I love look #2!!

    9.26.18Reply
  25. What beautiful outfits! Love all of these.

    9.27.18Reply
  26. So many darling looks here! Great inspiration for the chilly season <3

    https://www.eternallyelle.com/

    9.27.18Reply
  27. Raquel

    Hi Caitlin! Really love this post! It is SUPER helpful. However the link for the suede skirt isn’t working 🙁

    9.27.18Reply
  28. the photos are splendid
    Thank you for your good mood everyday

    Créoles or, Pendentifs croix, pendentifs animaux et pendentifs enfants sur Krossin.fr

    9.27.18Reply
  29. Love those olive green jeans!

    So sorry about your luggage! The same thing happened to me when I traveled to Aspen last year. It made me realize how much I overpack and how little I really need!

    9.30.18Reply
  30. carol

    you used to actually post and link accurate reflection to what you were wearing. so sad you’ve given up….

    10.1.18Reply
    • Hey! Did you read what I wrote in the post? Most of these pictures are from years ago (even as far back as 2013) and so the exact items I’m wearing have been sold out for a long time! I linked to the most similar items I could find. The point of this post was to provide fall inspiration! 🙂

      10.1.18Reply
  31. Wow You looking very nice and pretty derss,
    http://www.swarnprastha.com/

    10.2.18Reply
  32. Lynn

    You have amazing style! Great photography. I want one of everything you wear!!

    11.19.18Reply
  33. SALLY

    Happy Fall to you. I can see you are so ready for fall fashion. Me the only fall fashion I wore was jeans and sweater because of a noreaster last week. That was the first time I wore jeans since early May. Too warm today for fall fashion but its coming soon. Today its a little summer white dress with black ankle strap high heel sandals. Pool/beach days might be done here in Virginia Beach. Next 2 weekends might be too cool for that. I do have a trip to Long Island NY in late October for my Dad’s big 75 birthday party. It probably will act more like winter up there so I already have my winter boots and clothes packed and ready. We will be driving the tesla up so we will have to be ready for a good charge and knowing where the functional charging stations are.

    10.2.26Reply