Most Popular Fall & Winter Outfits

Fall and winter outfits are my absolute favorite to pull together!! There’s just something about knee-high boots, cozy sweaters, and bundling up with jackets and scarves! We’ve been on several trips lately (see Vermont here and England here) and I loved being able to put together some fresh, cold-weather looks!

I decided to put together this post of some easy outfit ideas that I’ve either worn in past seasons or have worn recently. Whether you’re looking for sweater and jeans combos, dressed-up layers, or just want some inspo to get you out of a style rut, I’ve got you!

Every look is linked below, and I’ll keep adding to it as the season goes on.

Southern Curls & Pearls wearing grey sweater, grey sweater duster cardigan outfit, fall sweater outfit

Similar Grey Duster Cardigan // Similar Grey Mini Sweater Dress // Similar Grey Scarf // Large Chanel 19 Quilted Handbag // Knee-High Brown Boots // Amazon sunglasses

Outfit on the left: H&M quilted jacket (sold out, linking similar here) // H&M plaid mini skirt // Brown turtleneck // Frye leather boots // Ralph Lauren Mini Polo ID shoulder bag // Miu Miu Oval Sunglasses

Outfit on the right: Revolve brown wool jacket // Revolve brown mini skirt // Vince Camuto Lumina boots // Sheer tights // Burberry Medium Bowling bag // Miu Miu Oval Sunglasses // Heaven Mayhem earrings

Couples Outfit in England, Fall trousers outfit, Burberry bag, Burberry scarf

Sam Edelman brown wrap coat // Favorite Daughter white bow top // A&F beige trousers // Brown suede belt // Brown suede heels // Burberry Medium Bowling bag // Burberry scarf // Miu Miu Oval Sunglasses // Heaven Mayhem earrings

Outfit on the left: Sam Edelman brown wrap coat // Ralph Lauren sweater maxi dress // Sam Edelman ballet flat // Ralph Lauren Mini Polo ID shoulder bag // Brown suede belt // Miu Miu Oval Sunglasses

Outfit on the right: Amazon brown and white sweater // Good American skinny jeans // Leather riding boots // Miu Miu blue light glasses // Burberry Medium Bowling bag

Outfit on the left: Ralph Lauren Green Quilted Jacket // MOTHER Skinny Jeans // Vince Camuto Mahogany Knee-High Boots // Ray-Ban Kai Sunglasses

Outfit on the right: ASTR Brown Plaid Vest // ASTR Brown Plaid Shorts // Vince Camuto Mahogany Knee-High Boots // CELINE Triomphe Shoulder Bag // Miu Miu Oval Sunglasses

Revolve White Cropped Turtleneck Sweater (almost sold out, linking similar option here) // Revolve Brown Maxi Skirt // Sam Edelman Leopard Mary Jane Flat // Amazon sunglasses

Outfit on the left: belted wool coat // similar lounge set // AIRE Sculptor tortoise sunglasses

Outfit on the right: Demellier shearling tote bag // similar plaid boxer shorts // similar Free People cardigan // Amazon sunglasses

Meshki Denim Vest // Meshki Denim Shorts // Marc Fisher Brown Knee High Boot // CELINE Triomphe Shoulder Bag // Amazon sunglasses

Outfit on the left: chocolate brown sweater dress // Demellier shearling tote bag // Dolce Vita sock boot

Outfit on the right: Zara Suede Blazer // White Layering Tank Top // Black Pleated Miniskort // Vince Camuto Mahogany Knee-High Boots // CELINE Triomphe Shoulder Bag

& Other Stories Brown Trench Coat (sold out, linking similar option here) // Free People White Sweater Set // Vince Camuto Mahogany Knee-High Boots // Brown Mini Handbag // Miu Miu Oval Sunglasses

Outfit on the left: similar grey turtleneck sweater // faux leather leggings // similar Chanel boots

Outfit on the right: Tularosa Bailey Jacket in Black // Similar Black Tall Chelsea Boot // Large Chanel 19 Quilted Handbag // Amazon sunglasses

Amazon Cropped Trench Coat // AGOLDE Straight Leg Jeans // Sam Edelman Tan Suede Booties // Miu Miu Oval Sunglasses // CELINE Triomphe Shoulder Bag

Like I said, I will keep adding outfits to this post as the season goes on, so check back soon for even more fall inspiration! 🙂

Leave a Comment

35 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