Three Fall Outfits

In the fall, as the air grows crisp and the days get shorter, it’s always great to have those clothes you pull on again and again. We often spot our friend Gaby, a curator at Etsy, around Brooklyn wearing the most amazing outfits. When she came to our most recent photo shoot, we asked her to share the three looks she’ll be wearing this fall…

Look #1: Mustard sweater, similar shirtdress, sneakers, similar tote

“My fall uniform usually includes a loose sweater; I like feeling comfortable. Even though I’m small, I typically avoid heels in favor of Vans or Converse. I’m always running around, and heels don’t last very long on NYC concrete. I also kind of like being little in a city full of tall people.”

Look #2: Plaid dress, sneakers, similar bag

“I love this dress because it’s so easy. Dresses are great when you don’t feel like coordinating an outfit in the morning. I’m not a morning person, so having to make decisions about my wardrobe can feel like a chore. Having a basic style formula has been really helpful for me.”

Look #3: Skater skirt, sweatshirt, sneakers, necklace, similar bag

“I’m currently going through a skirt phase, but, specifically, I’m obsessed with this skirt. It’s the perfect length and transitions from day to night. I’ll usually add one of my favorite Academy necklaces and Young Frankk rings. I like neutral colors, like the stereotypical NYC girl. Think of Woody Allen movies before 1985: everything is either an earth tone or black. In fact, I’d say Diane Keaton is my style muse.”

Thank you so much, Gaby! We love your style.

P.S. Six women’s beauty uniforms, and how to tie a scarf.

(Photos by Julia Robbs for Cup of Jo. Interview by Caroline Donofrio)

  1. I’d wear outfit #3 so often! Great ideas–thanks.

  2. Would love to know what that lipstick is, too!

  3. THe first one! The last one! Her gorgeous hair. I’m loving all of these looks but that mustard sweater. Beautiful.

  4. So cute! I loved all the looks, but I think my favorite was the 3rd. :)

  5. I am ALL for dresses for the same reason too! Great looks!

  6. So Pretty! She looks like a young Samantha Cameron.

  7. Cute outfits! Am I the only one who thinks Gaby looks a lot like Anne Hathaway?

  8. I love her style! She reminds me so much of Sofia Coppola, and that’s a major compliment to her, as she’s amazing. THink I’m gonna have to get that dress…..

  9. That mustard yellow sweater is gorgeous! I should definitely add more colors to my wardrobe. Thanks for the great inspiration!
    Katharina //

  10. I love all the three looks but definitely that plaid dress is to die for. Also, I love this girl, as I said in the makeup post where she modeled, she’s gorgeous and charming!

  11. What a fun post! I really like these ones : ) I’m definitely a fan of the mustard sweater look, though they all look great on your beautiful friend Gaby!

  12. She is charming! And I love her clothes, the colors and the textures.

  13. I’m obsessed with her haircut!

  14. Love the mustard sweater–I think I need it!

  15. She is gorgeous.

  16. if only to be as darling as your model! i just ordered the madewell sweater in mustard and sage. i hope they help soothe my nyc pangs that will go unfulfilled this fall…

  17. Those styles and looks are wonderful! I love your haircut it is so nice!

  18. S says...

    echoing some of the comments I’ve seen here. please expand models used! it’s so hard to find style blogs in the blogosphere for women between “thin, tall & white” and “plus-sized.” there are a lot of healthy and curvy women (and SHORT WOMEN) who would like to see styles that work great for them too!

  19. Definitely the mustard yellow sweatshirt outfit. It is so cute!

  20. Nina – totally agree with sumslay about the Converse. They’re not as bulky as some sneakers and are a such a classic. I’m a size 9, so I can relate.

  21. Gaby is so lovely! Love all three outfits!

  22. Jo says...

    I love Gaby’s make-up! I have similar coloring so would love to hear her beauty tips…future post?

  23. I happened to have just tried on that mustard sweater in a Madewell store today! (I tried the retro navy) – it was gorgeous, drapey and warm and flattering.

  24. Can Gaby be my personal shopper? Her style looks so effortless. I adore all of her picks but I’m head over heels in love with that last outfit.

  25. Ha, Nina, I’m with you with the large feet and sneakers! I find that converse (NOT WHITE, but grey are nice) are always flattering (something about the toe being a different color helps). I don’t do midi length skirts for fear of looking frumpy, but a nice knee length would be cute with the look as well.

    I looooove that she wears flat shoes – I’ve never understood how anyone in nyc could wear heels outside (maaaybe a low wedge, but that would be it for me).

    I love all these looks. Seriously – don’t even know which one is my favorite!

  26. Love all these looks! As a taller girl with size 9.5 feet, I always find myself looking akward in sneakers + dresses/skirts. Does anyone else feel the same?

  27. Perfect, love them all! I often joke with my friends that I dress like a 13 year old boy (t-shirt, jeans, sandals or sneakers) and my husband and I even dress alike. This is comfy and casual but still ladylike.

  28. cute, but none of these would work on my much taller, not so slim figure.

  29. Cute clothes for skinny girls, but shirt dresses are (often) not figure flattering on curvy girls/those with boobs bigger than an A cup.

  30. This gave me some cute ideas!!

  31. I love the mustard yellow sweater, and I would have never thought to pair it with a shirtdress, but I love the look!

  32. outfit #2!!! love it :-)

  33. I love seeing cute outfits featuring sneakers! No matter how hard I try to buy and wear heels they just aren’t practical for my daily life. Her looks make me want to try sneakers + a skirt this weekend :)

  34. I have to agree with netanya here! These looks are cute on this woman, but I can’t pull off these dresses and oversized sweaters with no shape, you know? I think it’d be nice to see different variations with the same clothes.

  35. It’s such a shame that you live in such a diverse city, but all of your models are thin white women. Don’t you think your readers might like to see looks for people of different sizes once in a while?

  36. Wonderful post! I feel so inspired for fall. Thank you! (I especially loved her jewelry :)

  37. I love the boyish, sloppy-chic look of all three…but whenever I try to pull this off, I feel like I look frumpy. What’s the secret? Do you just have to be waifish to pull it off?

  38. I second what wanderlustywriter said. I love, love the loose, drapey style of clothes, but it doesn’t quite work on the short curvy girls at all, no matter how hard I try!

  39. Love all of these because they look so comfy and practical and still cute.

  40. i love the first one. i’m nursing a 3 month old, so i’m always looking for stylish alternatives to the uggs nursing tops/dresses out there.

  41. That last look is my favorite. I LOVE that necklace!

  42. gorgeous as always! and i L O V E Young Frankk – every piece is amazing.

  43. I love the second look with the bold yellow. Her looks are layered to perfection, nicely flowy & feminine. Fantastic fall choices. :] // ☼ ☯

  44. Ooh I’d pick outfit 2, so so nice!

    Jade x ♡

  45. I love the look of these loose, drapey clothes that seem to be everywhere lately, but unfortunately they do not work on short, curvy girls. I’d love some kind of post on fall outfits for different body types, if you need ideas!

  46. I love the mustard sweater, but I also love the black skater skirt!

  47. I work as a stylist and love all of these looks! :) Happy Fall!

  48. I love ALL of these looks (perhaps because she is cute as a button!) but the sweater over the shirt dress really caught my eye, as did the Academy necklace. Will be hopping on their site very soon!


  49. Your friend Gaby is beautiful. I love her look. Oddball question for you: do you wear small socks in those type of shoes? Or go barefoot? As someone prone to blisters, I’m wondering how you stylish girls do it.:)

  50. The yellow sweater look for me please!
    I might pair with flats, though. Very warm and feminine.
    I am waiting for you, JG, to model these looks! You would look perfect in look #1.

  51. These are lovely! Since I recently transitioned into being a bike commuter, I’ve been struggling to find cute outfits outside of the standard leggings+shirt+flats I’ve been relying on. The length on these skirts/dresses would work nicely on bike (with maybe the addition of some trusty bike shorts underneath just in case!)


  52. Love these outfits for fall! I can see them working with flats or cute boots. The plaid dress and black skirt are now on my wish list!

  53. Comfy, effortlessly chic! I love a good mustard colored sweater and while I’ve never been a sneaker person til recently I think the lady sneaker game is great these days!

  54. That mustard yellow sweater is a dream – I cannot get enough yellow in my closet. Fall clothes are the most fun!