6 Fall Street Style Trends

Street style inspiration

This fall, we’ve been spotting pretty looks – from flower print dresses to cuffed jeans — on women around town. Here are seven inspiring ensembles I’d love to copy…

1. Above: Anoraks for the win. Such an effortless, laid-back style. (Similar here and here.)

Street style inspiration

2. A fun skirt can steal the show. (Three cute ones: Chevron, stripe and geometric.)

Street style inspiration

3. A pretty white top + high-waisted jeans + black flats = a forever classic combo.

street style inspiration

4. Floral prints are everywhere.

Street style inspiration

5. Cuff those jeans — then pair them with a James Dean-esque white tee and brown loafers.

Street Style Inspiration

6. Tucked-in sweaters. (Also socks with clogs. Love her.)

Thoughts? Which look would you wear, if any?

P.S. 9 fall fashion trends and how to look like a J. Crew model.

(Anorak photo and white top and black flats photo by Style du Monde. Patterned skirt photo, layered floral blouse photo and off-the shoulder top photo by Sandra Semburg. Floral dress photo by Mark Iantosca. Cuffed jeans photo by The Sartorialist. Tucked-in sweater photo by Where Did U Get That.)

  1. Susie says...

    I am dying to find the jeans in outfit #5 the high waisted Levi’s none of the wedgies appear to have that leg width… anyone know the style?

  2. Fabulous! I’m a fan of clogs always–and she’s pulling it off cute with her socks. I (impulse) bought a pair of Frye oxfords last weekend and am wearing them today with rolled up chinos. WHOOT!

  3. Stephanie says...

    Yee haa! Some brown skin at last! I love this blog but it is rather lacking in diversity. There is a lot of other beauty out there!

  4. love no.6 and no.7!

    Rachel x

  5. Madie says...

    Every time I see super high-waisted denim like that, I can’t help but think “long vagina, long vagina”. Anybody else? That’s a whole lot of zipper!
    Love the bold midi skirt. :)

  6. Maya says...

    I love the women of color represented in this spread! I have been reading Cup of Jo for many years now, and while I have enjoyed much of its content, it’s disappointed me in the past to see little diversity. I hope that such representation continues to grow on this site (particularly in the column on women’s beauty routines–seeing a curly haired woman as the subject in the last profile on beauty routines was so refreshing as a curly lass myself!)

    • Hear, hear!

  7. Erin says...

    Super cute post. Still can’t get over how AWFUL the clothes are this season, but do love how creative everyone is with the options… ladies making it lovely.

    • Tracy Distefano says...

      There’s a reason there was a spoof on Saturday Night Live about Mom Jeans, aka, high waisted Jeans – they are not flattering at all!

  8. yael steren says...

    I can’t get on board with the cuffed jeans. All it does it create a visual break at the bottom, which makes your legs look shorter. I think that there are a few trends you are missing such as menswear for women, military green, and fringe!!! xo yael

    • Agree!

  9. Tiffany says...

    Feeling the brown girl love in this post. and loving it!

  10. malaika says...

    now that it’s fall, I’ve been hunting for a solid, chic, NON-PUFFY winter coat. can you please do a post on this? I’ve looked at over 500 coats online and in person at the local shops but found nothing that’s a) an interesting colour (apart from black/brown/navy), b) chic with a feminine silhouette and c) at a price below $300.

    Thanks !

  11. Laura C says...

    Well, I guess that you can wear every trend in NYC…
    Clogs + socks are a no -no for me, but I like off-shoulders trend. So sexy.

  12. Love them all. .just will not be caught in the high waisted stuff. ..ewwww…just not for me!

  13. sg says...

    Yes to more posts with body types! I never consider any of the options posted, because I have an hourglass figure with short legs, olive skin, and long black, curly hair. As much as I wish I could rock Joanna’s style, I can’t because of the fit and color palette.

    I appreciate the diversity in complexions and hair types! Thank you for that here and in a little in your beauty ritual series!

    Love your blog and read every post —

  14. I love graphic print skirts! They make it look like I put more effort into my look than I did, which I’m always a fan of!

    Kristi | Be Loverly

  15. TootieMcBear says...

    I love the high waisted jeans and sweet white shirt look. I think it rocks on thin women. But if you aren’t thin, mom jeans do come to mind. Amanda Brooks had an Instagram post a few weeks ago of herself in J.Crew’s high waisted point sur denim jeans and she was looked so 70’s chic. I loved it.

    I do love florals, but short girls cannot wear floor length dresses. I would look like Laura Ingalls Wilder!

    Some of it feels like very thought through unthoughtfulness.

  16. I love this! Those midi geometric skirts really get me, and I totally adore that white top + high waisted jeans + super cute flats — I totally agree that it is such a classic.

    And SHOULDERS! My grandma always told me that shoulders were very sexy…gotta break ‘em out more :)

    Luscious + Intuitive Eating |

  17. I LOVE THE LAST ONE – and I have those clogs. :)

    • love that outfit too. What brand are the clogs?

    • eg says...

      look like Swedish Hasbeens.

    • Bianca says...

      the whole last outfit (including the shoes) is from american apparel! <3

  18. Danni says...

    Natural hair!!! Love it.

    • laura says...

      YES!!! <3

  19. I love outfits 2 and 3!!! WHERE IS HER SKIRT FROM?

  20. I think I spy the gorgeous Kate Foley in that floral dress! Recently shot her for Barneys and remember he wearing a gorgeous floral skirt as well. Such an inspiration!

  21. Katharine says...

    Love some of these, can pass on others but what I find fascinating is that the majority of these women have a phone in their hand. I carry mine around too but it struck me in these photos, it’s became such an accessory.

  22. Patricia says...

    Love the sweater, but I’m not sure I can get behind that tucked in part. Seems like it would be really uncomfortable + impractical.

  23. This Off the shoulder top with ripped jeans is the look I love most! The idea of a tucked in sweater is more has more panache than the regular way! xo

    adorn la femme

  24. Linda says...

    I’m always up for a beautiful white shirt, especially if it has embroidery! I’m happy to add florals into the mix and I picked up a couple cute flannels at Old Navy this week. I showed my husband the high waisted jeans and asked him what he’d call them, and he said, “Those are totally mom jeans, aren’t they? Yuck!!” So no, I can’t embrace that trend at all, because I think I feel the same way, especially since I’ve got hips. :)

  25. Jenny says...

    Joanna, I love your blog! (that’s always the start to a critical comment isn’t it?) I’m sad that in many of your fashion posts, all of the body types are pretty similar. Like, in your one about dresses, they were all high crew-neck dresses, which are great for your (awesome) tomboy style but don’t exactly work with my 36DDD frame. I’d love to see some variety!

    • Joanna Goddard says...

      thank you so much for your note! yes, you’re right. I am going to concentrate over the next few months on featuring more body types and fashion that will fit on all shapes and sizes. i can definitely get stuck in the mindset of my own body, since i’m used to shopping for myself, but i’m going to do better! thank you so much, jenny.

  26. Amy says...

    I don’t know-those jeans and james dean shirt look like unflattering “mom jeans” to me in the worst way! Bravo to these ladies for wearing what makes them comfortable, but I’m not feeling the trends this fall. Not for me.

    • I agree. I’m still getting over my ’90s hideousness and have to somehow embrace mom jeans now. Definitely takes a certain lady (whether its confidence, body type, or both) to pull it off, though my wide hips cringe at the thought…

  27. Erin says...

    I love all these! But I am once again struck but the endless stream of rail-thin women you share on your site. I would love to see how these fall trends look on an even slightly less supermodel-sized

  28. plch says...

    the ’70s are definitely back! (… I liked them the first time around)

  29. Sara says...

    That anorak in the first photo is EXACTLY what I have been searching for, for a trip to Seattle in a couple weeks! Wish I could find just that one, seems almost American Apparel-y, but no luck there. Any ideas?

  30. Nice selection of Fall Street Style trends. I’m starting to fall in love with geometric shapes and bold colors to add to my wardrobe! :)

  31. Mary Jenkins says...

    Love all of these! (And that skirt!)

  32. I love that third look… those high-waisted jeans fit her perfectly! So simple and feminine.

  33. the other day my friend said she’s seen a trend of “Amish chic” styles popping up all over New York lately lol! #4 is my idea of what she means.

    Not sure I could pull the look off but these girls look ethereal. ugh, models ;)

  34. I LOVE all these trends!! I’m definitely going to be trying them all, especially no 3. Plus, I love their hair (7 &1!)! Thanks for sharing Joanna!

  35. Awads says...

    I think i hated every one of those looks, esp. that long floral dress. eeesh! I’m going to stick with the plaid flannel look you turned me onto earlier for the fall.

  36. Love the colorful skirt. Such fun trends! So glad Fall is here!

  37. Wanting to steal ALL OF THESE.

    XX Laura