12 Fall Dresses

12 Fall Dresses

Mark your calendars: September 23rd is the first day of fall. I’m looking forward to fall weather, along with apple picking, pumpkin carving, walking in crunchy leaves, the whole shebang. The boys even have their Halloween costumes picked out (Toby’s, Anton’s, haha). So, to get in the spirit, here are 12 dresses that would look cute with tights and boots as the days grow cooler…

Click or tap on the images, if you’d like!

Thoughts? Which would you wear?

(Top photo via Madewell. Layout design by Miss Moss for Cup of Jo.)

  1. loving the look in the top photo with the same color sweater tied around the waist.

  2. Thank you for this guide! I love fall, but always have a hard time finding dresses (my favorite thing to wear) that match the season. Time to go online shopping :)

  3. Cynthia says...

    I like them all, but the buffalo check shirt dress and the tie-front plaid dress are the ones that would work for me. I dearly love the
    drop ruffle dress, but I have to remember I’m not in my thirties any more. I love sweater dresses, and used to wear them when I was thinner.

  4. That check dress from ASOS is really cute! I love the shape. Too bad it’s already out of stock. :)

  5. Dee says...

    Where is the dress in the main pic from?!

    • Genevieve says...

      It’s from Madewell!

  6. yael steren says...

    It’s hard to believe it’s almost fall because it’s still so nice out in NYC! I remember last year for fashion week I was wearing long jeans and a leather jacket and this year, I was warm in a skirt!! I’m torn because on the one hand I’m psyched for fall fashion but on the other hand, fall means that winter isn’t too far behind and I’m not a fan of the cold weather (or taking blog posts in it)! LOL! xo yael

  7. Sharon Sorour-Morris says...

    Hmmm … I love the simplicity of the black patch dress from Zara and the soft cashmere LBD from Whistles. The others are a bit footloose and fancy free for me – too old and too short, I am! Oh, and the SHOES the model is wearing with her fawn and white fall flutter dress – those are fab!

  8. ASOS knows how to do dresses right! I need to get my hands on a plaid dress

    Happy Medley

  9. Kirsten says...

    Oh my gosh that cashmere turtleneck dress is amazing but so out of my budget!!!

  10. Trying to embrace these but keep thinking they look a little too much like nightgowns made from pillow cases.

  11. I love the patch dress! I wants!!!!

  12. tracey says...

    My favorite fall dress at the moment is
    this one

    It’s ethically made, comfortable and cute. I wear it on weekends with flats and dress it up at night or for work.

    • Amy says...

      Ooo! Yours is my favorite!!

  13. Would Buy 1, 6, 9, 10 in a heartbeat! Here in Marbella, Spain, real boots-and-tights autumn might not start until late November, but stocking up on dresses is always a good idea ;-) Great post, thanks!

  14. These shapes really don’t work for my current body type (nevermind the fact that I’m pregnant, too!), but I think the Fall Flutter dress is simply lovely. Exactly what I would have worn when I still had a tiny waist before babies!

  15. Have to agree, I’m a little tired of the shapeless look. It looks ADORABLE on lots of ladies. But I am a tall girl (6′ 3″) so wearing something that baggy just doesn’t flatter :) LOVE Madewell, hopefully they throw in more fitted dresses later in the season

    • Sonya says...

      I’m not a tall girl (5’6″) and athletic build, but I am also tired of the shapeless look. I have a figure and would rather it be accentuated than hidden.

  16. So funny I actually just bought the last one and I love it!

  17. I love the plaid tie-front and navy cashmere options! My straight figure, long torso, and comparatively short legs make some of the other shapes hard for me to pull off. Great assortment of different lengths/shapes here…I bet everyone could find at least one that works for her!

  18. Feeling rather hip that my dress from last weekend made your list (wink) – might be the first time in my life that I’m “on trend”. Great list Joanna!

  19. Teri says...

    I loved the cashmere dress! Then I watched the runway video and suddenly the model had saddlebags. Darn those side pockets!

  20. May says...

    Grey Check dress! It looks comfy and forgiving. Love the neckline, sleeves, and hem. Best check dress I’ve seen in ages.

  21. There is something soo perfect about the belt tie on the plaid tie front dress . Wide and flat at the hip, bow off center. Stylin, baby!

  22. Heidi F says...

    Cute! Looking for more midi or at-the-knee options!

  23. I’m crazy for the shift dress–love the checked one!

  24. Dresses look great on the models, but as a petite curvy girl, I cannot, cannot pull off the shapeless dress trend. Have to say I will be very happy when it’s over and fit and flare dresses become more prevalent again. Until then, enjoy these dresses, those of you who can pull it off!

    • Val says...

      From one curvy girl to another: amen sister! : )

    • Rebekah says...

      Me too! This petite and curvy body does NOT work with the whole “flannel pillowcase” trend! I much prefer tailored looks.

  25. I loved the H&M selection and the drop ruffle dress. H&M is in my budget but unfortunately not the ruffle dress! Thanks for sharing these, they are super cute, and have got me thinking of winter, and boots!

  26. I like the plaid dress with the tie around the waist. I like sweater dresses on others but they make me feel so stuffy.

  27. I love all of the plaid dresses! The pattern is perfect for fall and goes well with ankle booties :)

    Meet Me in Midtown

  28. I’m a sucker for navy cashmere anything – love that dress. Great picks!

  29. Love the thought of tights and boots and warm slouchy sweater dresses! I wish I were back in my hometown in Connecticut when the fall rolls around…miss the crisp cool days and gorgeous foliage! xo

    adorn la femme

  30. These are all so cute. Probably my biggest gripe in life is the fact that my hips make sweater dresses impossible to pull off. I covet them SO MUCH and probably will try them on again this year, as I do every year, eventually concluding that, like the word “fetch,” it’s just never going to happen.

    • Joanna Goddard says...

      caroline is actually wearing it today! so cute in person.

  31. Mary Jenkins says...

    Pretty! I’m so happy about the turtleneck dresses. I have always really liked them and am glad they are back. Something so chic about them!!