Four Fall Outfits

My friend Kendra—who recently moved from New York to northern California (break my heart!)—always has inspiring style. She looks laid-back, but her outfits have a bit of a twist. Here, she shows the four ensembles she’s wearing most this fall… …

Look #1: Similar sweater, jeans, fedora, flats (update: now sold out everywhere! but there is a similar pair here)

“I was psyched to find these flats. They’re feminine but still have that loafer shape I was looking for. I wear them with absolutely everything. I’m trying to change up my silhouette a bit—I’ve worn skinny jeans for like 10 years now so I finally got a pair of boyfriend jeans. I like the loosey goosey look. And this hat is my staple; it can dress up any outfit. When I’m wearing it, people think I’m a designer! A guy hit on me in Whole Foods. Maybe the hat makes you look mysterious. I was on the edge of buying it for years; I kept mentioning it to my friend, and she ended up buying it for me as a gift before we moved.”

Look #2: Similar tank, skirt, bracelet, clutch, booties

“I don’t usually show a lot of skin, but I love this trend of a high-waisted skirt and knotted shirt and just showing a tiny bit of tummy. I’m trying to get away from always wearing black, and I’m feeling inspired by burgundies this season. For styling, I pretend the skirt is a pair of high-waisted jeans, so I’d pair it with things like a cropped sweater or a button-down shirt with that front tuck that everyone’s doing.”

Look #3: Men’s cardigan, white shirt, black jeans, flats (update: now sold out everywhere! but there is a similar pair here)

“I love these Target jeans—I’ve had them for six years, so the hole in the knee is real! Last spring, I had an overwhelmingly busy few weeks, so one night, I decided to have a glass of wine and line up a bunch of outfits. I was feeling it that night and was being more creative with colors and combinations. And I ended up having the smoothest three weeks after that! Every day I liked the way I looked and didn’t have to make any decisions in the morning. I’d love to do that again.”

Look #4: Overalls, tank, bracelet, Wayfarer sunglasses; floral toddler dress

“Overalls are a new thing for me. I haven’t been brave enough to wear them off the beach—still can’t decide if they’re a yes or no! One fun way to try out new pieces is to do clothing swaps. It’s a great motivation for cleaning out your closet. You spend a great night with girlfriends and go home with a couple pieces you’re excited about. Win win.”

Thank you so much, Kendra! Your style is amazing. And I miss you:)

P.S. How Kendra gets such awesome hair, and our friend Gaby’s three fall outfits.

(Photos by Maria del Rio for Cup of Jo)

  1. gladmama says...

    This has been my favorite post, I love the style and finally found the d’orsay flats for $100!!!!! On Loeffler’s website.

  2. ooh these are lovely outfits but look like they are for summer !!!!

    during autumn it’s already too cold to wear anything but long sleeves and jackets and boots – can you do a feature on how to look cute while staying warm??

  3. Haha, I thought I was the only one nerdy enough to line up outfits in advance! Shouldn’t admit this publicly, probably. But I feel like it both saves time in the morning and makes me look better/not like I chose my outfit while half asleep.

  4. Her style is beautiful and really inspirational. Just the style I like–minimal yet feminine and sexy. Please feature more of her!

  5. Her style is beautiful and really inspirational. Just the style I like–minimal yet feminine and sexy. Please feature more of her!

  6. love that overalls!

  7. I love her style. I totally agree with her about the hat. I bought a very similar style hat by Eugenia Kim at shopbop. I get so many compliments when I wear it; mainly from men.

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  9. Beautiful outfits. I’m wondering what size she is wearing in that men’s cardigan. I’m probably around her size, but am wondering if getting an XS would defeat the purpose of wearing a men’s sweater?


  10. LOVE Kendra!!! She’s an amazing prop stylist guru, mother, and taste maker! So happy to have worked with her! Congrats Kendra, and family!💕💕

  11. I like how the outfits are comfy and fashionable. And I love the addition of the fashionable little girl!

  12. She looks good in all the different looks but I especially like those overalls. Much better than the typical farmer looking overalls.
    I agree, her hair helps a lot with her style.

  13. thanks for all these nice comments! i know kendra will be touched :)

  14. @shed, age is just a number so if you like overalls, go for it! :)

  15. Her hair is beautiful! I am super jealous.
    Those flats from shopbop are great, they look like the perfect blend between comfy and feminine. I have been living off of different colored Toms but maybe I should make the plunge to a sexier pair of flats.
    The overalls is a look I have tried and failed at, I wonder if I am just too short. It looks fabulous on Kendra but I think her body type would be perfect for any style clothing.
    I agree with Kendra on switching to boyfriend jeans from skinny jeans. It is a comforting yet still feminine switch for the fall.
    What is your go to fall full outfit?

  16. Great photos! I love her style and every outfit she’s wearing, it looks so normal but at the same time with style. And I think I’m gonna try what she did… a cup of wine and get ready several outfits for the week. Love the idea!

  17. those overalls YES YES YES YES. probably going to order a pair tonight.

  18. Wow, I love all of the outfits! I feel most inspired by fall fashion. Being from the PNW, I loved a lot of these outfits. Thanks!

  19. Look #1 and #3, comfy, laid back and so my style. :)

  20. I love the fluffy black sweater from the first outfit, but the second outfit has got to be my favorite! -Audrey | Brunch at Audrey’s

  21. Okay, HOW do you pull off wearing baggy sweaters and overalls and still look put-together???

  22. Great outfits and such a natural beauty! Now to find those flats…

  23. I love this series you’ve started! It’s so inspiring! Do you happen to know someone in a rainier climate (like us out here in the pnw) who you could feature? I’m losing a lot of inspiration as the days get shorter and the endless rains of autumn start in. Oh to be a Californian!

  24. I love your posts featuring Kendra — she always looks so chic & put-together! I still refer to her 3 ways to tie a scarf guide every so often :)

  25. This was such a fun post. I love her style. Thanks for sharing!

  26. Beautiful photography, beautiful girls!

  27. I love the overalls! I think they are timeless and look just as good on women with silver hair as on younger women.

  28. Can Kendra give us her beauty routine! Totally gorge!

  29. oh my gosh….just bought the hat…reason #12596 that I shouldn’t read style blogs! can’t wait for it to arrive. oh so chic!

  30. I loooove that dress and the cozy sweater!!! :)

    p.s. agree with others, the location is magical!

  31. kendra is SUCH a babe. i have always loved the posts that include her! (and kendra, GIVE ME YOUR HAIR.)

  32. love her hat! do you know where it’s from??

  33. wow, great outfits!
    xo, cheyenne

  34. Amazing style. LOVE.

  35. Love the overalls, but wondering if they work once you’re are of a certain age? What do you think? What’s the cutoff number?

  36. I’m inspired to get a fedora now! Even though I usually have to style hats in order to look cute in them. I clicked on the overalls link almost immediately but…they look cuter on Kendra than on the model! Which makes me wonder how they will look on me…

  37. @gilly, they were taken in northern california—in marin, north of san francisco. soooo beautiful, right?

  38. Where are these pictures taken??? Breathtaking scenery.

  39. Best part of all these outfits…her hair. OMG it is amazing.