Style

Pretty Dresses for Fall

12 Fall Dresses

Where are you shopping these days? It’s *finally* tights and boots season, and I’ve been on the hunt for pieces I can wear into the winter. Here are 12 dresses that are easy to toss on as the days grow cooler (including a pretty green number under $35)…

Thoughts? What are you wearing on repeat these days? I also have my eye on these.

P.S. The best pants and shoes for work, and an ode to midi dresses.

(Top dress by Nani Pani.)

  1. Caron says...

    I got the corduroy dress and am wearing it today. It’s so cute and comfy. Perfect with Allbirds Skippers now and boots/tights when it gets colder. Thanks!

  2. Erica says...

    This post definitely confirms for me that 90s fashion is coming back. I did a double take because I wore almost the exact outfit ( the corduroy dress) in my 8th grade school picture in 1995. Bangs and all. Twelve year old me is very proud!

  3. elle says...

    Wait, where can one get the dress in your featured photo? Of course that’s the one I want!

  4. Sasha says...

    Several of these are button fronts- would they be good for nursing? I gave birth 3 weeks ago, and am realizing most of my clothes will not work for nursing my daughter.

    • Abesha1 says...

      Hi- The thing about buttons is you have to get the whole breast out, so they’re good (easy access) and bad (fairly exposed). I don’t believe nursing needs to be covered up, but I don’t generally show much skin, so I often used scarves to cover my chest/upper breast (but not baby)
      when nursing in button downs. Also, for pulling up instead of wearing buttons, a friend used to drape a scarf down the side of her body, which I thought was genius, as baby covered her front but shirt pulls up along sides a bit.

      Try nursing in front of a mirror if you want… and congratulations! It’s a wild ride.

    • kp says...

      Me too! I was excited to no longer have to wear maternity clothes but now I have no idea how to dress nice again while easily breastfeeding.

      Thanks for the tips abesha1!

    • Diane Bengson says...

      Though it’s been many years since I’ve nursed a baby, I liked wearing loosely fitting knit tops, and pulling them up from the bottom. Another great trick is a cardigan or jeans jacket for additional coverage. Judging from how people would come up to talk to me, I think they rarely noticed I was breastfeeding. Good luck!

  5. Jessica says...

    But, but, but… what SHOES are you wearing with these dresses? Low boots seem a bit off, ballet flats a bit too feminine, converse seems like a good way to “dress down” but they are canvas and it’s about to rain…
    Help!

    • Claire says...

      oxfords or wingtips? Something from Red Wing Heritage, or some handsome high boots?

    • Jo says...

      Mules!! Madewell has great ones right now and Rachel Comey’s Mars mule is perfection.

  6. The dot shirt dress is gorgeous, so pretty!

    Rebecca

  7. Claire says...

    all so pretty! I used to wear dresses everywhere, and I’ve gotten away from it. But this is inspiring.

  8. I especially like the midi wrap and dot shirt dress!

  9. Tania says...

    I bought a Blue chore coat at Old Navy in the boy’s section for $10 on sale recently and have been wearing it obsessively! I thought this trick might be forbidden for someone my size (I’m a size 12, 5’7”), but nope, the XXL size fits perfectly. And what do you know, I thought I’d discovered this brilliant secret, but I ran into the most fashionable Mom in my nabe at the playground and she took one look at me and said, Old Navy? She has one too! She’d asked a little boy’s father where the boy had gotten his. So now the secret’s out: https://oldnavy.gap.com/browse/product.do?pid=204329002&CAWELAID=120299900000933348&CAGPSPN=pla&CAAGID=35201331985&CATCI=pla-519003303808&tid=onpl000000&kwid=1&ap=7&gclid=EAIaIQobChMI1qv4nYDZ3QIViJ-zCh0O2AJxEAQYASABEgLvI_D_BwE&gclsrc=aw.ds

    • Danielle says...

      Oh man now all I can think about is this jacket! XXL is sold out and I’m wondering what the chances are I could squeeze into an XL haha.

    • Tania says...

      I would say if you are about a size 8 women’s you could fit in the XL!

    • Joanna Goddard says...

      so cute, tania!!!!

    • Danielle says...

      Thanks! I feel like as long as the sleeves/shoulders fit I might not care if I mostly leave it unbuttoned.

  10. Cynthia says...

    It’s nice you showed some dresses from Target. While so many people are into ethically sourced clothing, it’s usually beyond my budget. I’ve just retired, and while I’m comfortable, I have to watch my spending.

    • Joanna Goddard says...

      thank you, cynthia! we always to try to feature a range of prices, philosophies, styles, etc. xoxoxo

  11. Kate says...

    I’m all about these dresses, but it’s the tights part that I fail at over and over! Any suggestions for comfortable, durable tights for a girl with not tiny thighs and butt? (Hue doesn’t work for me.) Curvy girls out there – tips? Help!

    • Cynthia says...

      Try Nordstrom brand tights. They fit great and last forever.

    • sam b. says...

      I find that uniqlo’s tights are comfortable – I am a 12/14. The waistband doesn’t move or roll down, which is my main problem.

      I am curious about Heist tights- they seem miraculous, but are a little pricey.

    • Stacie says...

      I LOVE the Assets brand from Target, which are made by Spanx. Same here with the bigger thighs – they never pull down! I buy the higher waist ones, which are about $20 and last for a season or two.

    • Amber says...

      Second the Nordstrom brand suggestion. I have the fleece lined ones and loooove them (I’m also not tiny on the bottom half). They’re the only tights I’ve ever worn that don’t uncomfortably cut off my midsection, but still stay up!

    • Kate says...

      Thank you for all the tips so far! I’m going to try all of them. Keep the recs coming!

    • Danielle says...

      I second Uniqlo and Target! I’m also a big advocate of sizing way up. I found this out when I needed tights in a pinch and the only ones available were a few sizes too big. They were so much more comfy and the opacity was way better.

    • Kate says...

      @Danielle *face palm emoji* duh! I should have been doing that this whole time! I think I usually only look for tights as an afterthought when I’m at Gap or JCrew and they only ever go up to an L and the L definitely doesn’t cut it. Thanks!

    • Katherine says...

      You gotta find non control top tights. It’s the control top that’s miserable. Although I do like Assests brand and just buy a size up. I still wear my maternity Assests tights too!

    • Joanna Goddard says...

      so pretty!

  12. Emily says...

    Any tips on how to wear such a feminine style? I love it but always end up looking so prissy when I try!

    • Jenna says...

      How to not look overly precious or cutesy in feminine dresses would be a fun blog post to read, I think. (Although there’s obviously nothing wrong with looking cutesy if that’s what you’re going for.)

    • Roll the sleeves up, add Converses on the bottom! Should remove prissiness (but I am sure you look delightful as you are).

    • Erin says...

      Try balancing a flowy, feminine dress with something more structured or edgy… a courderoy blazer, leather biker jacket, chunky boots, etc.

    • Ro says...

      I’d like to know this as well! I’m very attracted to the comfort and look of dresses, but when I wear them I feel sooo unlike myself. My plan this fall is to pair them with big chunky boots to toughen them up, but I’d love to hear other ideas as well!

    • Claire says...

      As others have suggested, consider adding more tailored pieces. You can put a men’s vest or jacket over it, or a long sleeved t-shirt under it. Sometimes a leather belt looks nice. And I love a feminine dress with Oxford shoes, wingtips, or cowboy boots…or any boots really. The short ankle-high boots look terrific w/ a dress and tights.

    • Jessica says...

      Yes! I would love to see a piece on STYLING these dresses realistically for a woman with too little time and messy kids.

  13. Laura C. says...

    I wear these days only jeans and t-shirts and flats. We need to wait another month until tights and boots season and I can’t wait. I love the tie neck one. Thanks for the inspiration darling!

  14. Nikki says...

    Botton front?

    • Stella Blackmon says...

      Thank you for catching this! x

  15. Sheila says...

    I saw the green shirred sleeve dress today at Target and fell in love! That animal print midi wrap dress and the polka dot one are also to die for. Too bad I’m on a self-imposed spending moratorium…trying to save for a down payment for the house I’m buying in December = no new clothes for Sheila!

    • Sasha L says...

      Good for you Sheila!! It will be so worth it.

  16. Joaquina says...

    Ah man the midi wrap is sold out, of course! Love the length and design.

  17. Georgia says...

    I’m loving how many fair trade and ethically made dresses you have listed- and all from different companies! Way to go, CoJ.

  18. M says...

    First off, I love the blog and your lists. I must add it has been bad for my bank balance but I love being here and reading comments and the thoughtful articles you guys post. Great going.
    BUT, I have to add – 218$ for a cotton gauze dress from India? It is sooo overpriced since cotton dresses even in pretty prints cost much less in other India based websites (In India, this dress would be less than $20)! Everything listed here, save for the one Target dress is over 150$!
    Is shopping for such expensive clothes considered passe? Won’t it be more effective if COJ can point to lesser known names or brands to save some pennies? Is it prudent to indulge and tempt readers with clearly overpriced clothes lists?
    With other thoughtful posts about being financially secure, saving pennies, putting together wardrobes with what one has in their closets, these lists featuring such overpriced dresses seem so odd.

    • Joanna Goddard says...

      thank you so much for your feedback! we always try to feature a range of different pieces, since we know our readers look for different things. some readers request ethically made clothing, some readers request lower price points, some people request petite sizing, some people request plus sizes, etc. we love and welcome all these women and strive to have something here for as many people as possible.

      regarding budget, we included some ethically made clothing, which tends to have a higher price point, yet you’ll also see a range of others here — from aritzia, madewell, loft, elloqui, target, etc. — that are less than $150.

      thank you so much, M!

  19. Lesley says...

    Thanks for including plus size options!