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Three Fall Bags: Which Would You Choose?

Growing up, the end of August was one of my favorite times, due in large part to back-to-school shopping. Excluding the year my mom bought me a leather briefcase — I looked like an eight-year-old reenactment of a John Grisham movie — choosing a new book bag was my favorite part. Every September, I try to honor this tradition by investing in a new bag. So this year, I visited Cuyana’s NYC flagship to see what’s new…

I arrived at their beautiful Soho store and was like, “Oh, hiiii, bags.” The bags did not greet me back, but they perched happily on their shelves, which was just as nice.

I also said hi to some clothes (including the dress I am wearing in these photos). Because, you know, when in Rome. Then, it was time to get down to business.

First up was the work clutch in caramel. The color feels distinctively autumn, like a beautiful gourd that happens to hold your essentials. Unlike a gourd, however, it’s appropriate to bring anywhere, from work to dates to dinner. When it comes to bags, I look for something timeless, that will last for years to come. This style is a winner.

Next up was the mini circle belt bag, which adjusts to sit on your waist or hips. Because sometimes you just want to go hands-free without looking like a tourist.

Three Bags for Fall

Third, I went for the tall structured tote in burgundy. (Because, I ask you, what could be sexier than burgundy?) As with all Cuyana totes, it’s made of soft, buttery leather and fits all the essentials. Its taller height means your things stay nestled safely within.

Cuyana NYC Store

Cuyana’s philosophy is “fewer, better things,” and I couldn’t agree more. If you’re in the market for a fall bag, you can check out the full collection here.

Which bag is your favorite? Do you have an end-of-summer tradition?

(Photos by Christine Han for Cup of Jo. This post is sponsored by Cuyana, a brand whose mission we love. Thanks for supporting the brands that help keep Cup of Jo running.)

  1. Allison Gryski says...

    Hoow does “fewer, bette”r align with buying a new bag very September?! How much is enough?

  2. Rae says...

    Please tell us what you’re wearing on your lips!

    • Caroline Donofrio says...

      It’s Bobbi Brown lipstick in “Raisin,” but a suuuuuuper light coat, applied with my finger instead of from the tube.

  3. Andrea says...

    I’ve had the zippered tote for about 8 months now and LOVE it. Feels waaay more expensive than it actually was.

  4. Ingrid says...

    I’d choose the dress!

  5. A Martin says...

    The mini circle belt bag is soooo cute!!! It is going on my wishlist.

  6. Marina says...

    This is off topic, but Caroline, do you still use the hot air round brush? Do you still recommend?

    • Caroline Donofrio says...

      I do! Hot air round brush forever.

  7. Traci says...

    I have the tall tote. . .2 actually and I love them. They are actually super sturdy and the leather is of great quality! I’m hoping to get a cross body for fall!

  8. Lynn says...

    Caroline, love all your posts! I apologize if this question is too personal, but what bra are you wearing? I am in a perpetual hunt to find a comfortable bra for strappy dresses like yours. Thank you!

    • Jen says...

      Yes, would love to know. Also, would love to know people’s thoughts on silk slip dresses on shorter (I’m 5’2″) and straight figured women. I love the versatility and have thought about buying a slip over and over, but can’t get over the image of me looking like I’m walking around with pjs.

    • MJ says...

      Upvoting this comment!!

  9. Carrie says...

    Random assortment of sizes you’ve got there!

    I’ve have my eye on the Madewell Transport tote, but the medium is too big and the small is, well, too small. The zip top doesn’t have an outside pocket otherwise it would be perfect!! Madewell, I hope you’re reading this ;) OUTSIDE POCKETS ARE A MUST

  10. Sarah says...

    After reading this post, I would love an update of Caroline’s Beauty Uniform. I’m curious whether she’s still using some of the same products, and whether she still goes bare-faced at night?

    • Mandy says...

      Me too!

  11. I love the first one. Caroline, you are such a natural beauty! xo

  12. Carolyn says...

    Much to my surprise, I am also totally digging the mini circle belt bag! Who knew?!

  13. I, for one, would love to see someone carrying around a ground full of their stuff.

  14. K says...

    Caroline – when is your book coming out? I can’t wait to read it!! :)

  15. Maggie says...

    I love Cuyana! I bought the Leather Tote 4 years ago and still use it every day. The leather is lovely, the straps are strong, and I love that it’s monogrammed as well. Thanks for spreading the Cuyana love!

  16. Nuriya says...

    I’m not a native speaker of English. I love reading Caroline’s post because I learn a lot of new words, like “gourd” :) thank you!

  17. Chelsey says...

    Caroline, you look so devastatingly beautiful! (As always, but with an extra punch).

  18. gfy says...

    You definitely look happiest in the burgundy tote bag, so I would get that one if you are trying to decide. Also, as another person of 5’2″…it is so nice seeing you photographed head to toe. It’s virtually impossible to see visuals of our size in clothes anywhere so I never know what clothes are going to look like on ME because a mirror in a dressing room is too brief an exposure to know for sure. Anyway, you look great! thanks~

  19. Ashley Deitz says...

    As a teacher, August is a new beginning that is nerve wracking and exciting! I love organizing my classroom and decorating but get so nervous even after years of first day routines and new students. I still buy myself a new first day of school outfit just like my mom used to do when I was a child. I loved those shopping trips!

  20. Suzanne says...

    I LOVE my Cuyana bag—years and tons of use later (ie. international travel, beaches, daily life) and the leather still looks clean and fresh.

  21. Elizabeth says...

    Caroline–you are simply stunning, and I love your writing! :)

  22. Kate says...

    I am a fan of buying quality goods and use it for a long time. However, using the word “invest” for buying expensive goods is just incorrect. It is a (necessary) expense.

  23. Briana says...

    Hope you bought that dress. It’s amazing on you!

  24. Darcy says...

    Yes, so many really good non-leather options out there. Matt & Nat, great. Why would I take the skin off a living creature to carry my iPhone and lipstick around? I don’t get it. (shrug)

    • I’m just curious….what are your shoes made out of ?

    • Jacqueline says...

      Agree!! :-)

    • Mary says...

      Technically, you take it off a dead creature ;)

  25. diana says...

    I would choose the circle bag!

  26. Liz says...

    Already received and wearing my mini-circle belt bag! At work, it lives inside my Cuyana tote that works as my “briefcase.” Yep, totally hooked.

  27. Roxana says...

    “Unlike a gourd. . . ” Haha! You are hilarious.

    I’d normally go for the tote, but I’m really digging the “hands-free” mini circle belt bag. Will have to check it out!

  28. Ceridwen says...

    The dress looks so pretty! Also, all the bags :)

  29. Cat says...

    I’d love to see some non-leather options for bags. I try to to keep in mind ethical/eco materials.

    • G says...

      Agreed! So far, I really like Matt & Nat.

    • Joaquina says...

      Thank you, Cat, for mentioning this! There are so many ethical choices (leather and suede production and by-products are also detrimental to the earth). Matt & Nat is a wonderful company based in Canada that offers recycled plastic for beautiful handbags. Really hoping Cup of Jo begins to showcase more eco friendly choices.

    • Ferrell says...

      I am always hoping for more animal-free accessories and shoes to be featured.

    • Vivian says...

      I agree too.
      I feel it is time for us all to take that leap to a more ethical lifestyle.

    • Samantha says...

      I totally agree with this, but here is another side of the argument:
      The meat industry is not going away. What happens to all of the animal skins that are by-product of the meat industry? Is it not more eco-conscious to purchase goods made from those skins (companies like Nisolo only source leather that is from the meat industry) rather than it being discarded?
      https://www.instagram.com/p/Bk2yaGngOw_/?taken-by=factory45co
      Some food for thought!

    • Jessica says...

      Hi Cat, I also like Matt and Nat, but would highly recommend Angela Roi. I have the Morning crossbody in burgundy and it’s gorgeous–people compliment it all the time, and it looks way nicer than a lot of vegan leather bags.

  30. KONSTANTINA HRYSANTHAKOPOULOU says...

    You look amazing Caroline! The bags are wonderful, the whole store seems delicicious. Sadly, a lot of these products aren’t available in Greece, so I am in love with Massimo Dutti bags for the time being.

  31. Shana says...

    Gorgeous post!! I only recently discovered Cuyana and I’m in love :) The tall bag is gorgeous!!

  32. Please tell me you left with that dress!

  33. Liz F says...

    All I could see in this post was how fabulous your eyebrows are, Caroline!

  34. Cuyana has such gorgeous bags! I keep meaning to buy some ones for travel! That burgundy tote reminds me a lot of Baggu, but alas, it’s such a simple style that I’m sure there’s many similar looking ones.

  35. Awads says...

    The problem i have with buying a new bag is what to do with my old bag(s)? I have a closet with several that i loved when i used them, but i almost never, ever go back to them. and i don’t switch out of bags often (except for going out at night). So they just pile up and now i’m a hoarder? what do you do?

    • Carole says...

      Oh my gosh! I have this exact issue!! I always feel bad buying a new bag because I know most of the older bags I have will just never get used again. I also have a closet full, I guess maybe donation? Or trying to sell at a consignment shop?

    • Michelle says...

      Do you have a local BuyNothing group? It’s such a neat hyper local community project that has helped me let go of a number of bags as well as introduce some new ones!
      Cheers!
      https://buynothingproject.org

    • Ana says...

      Donate or sell! I sell some stuff on poshmark and find the process to be easy and actually kind of fun. I also go through my closet 1-2x per year and donate a bunch of stuff to Goodwill or other local charity thrift shops. (I’m a huge thrifter so most of the stuff I’m donating, I bought from a thrift store to begin with, and I call this the thrift cycle of life!)

    • Amanda says...

      Donate them to a women’s shelter or Dress for Success? Or sell them somewhere like Crossroads Trading Co? I have a large bag of Fall items to donate to our local charity shop when the weather turns!

    • Sasha L says...

      Ana, the thrift circle of life! Yes! Me too. Love it.

  36. Ashley says...

    How tall is Caroline??? I have been admiring that dress, but I am only 5’2 and wasn’t sure if it would work on me. Dress looks wonderful on you, Caroline!

    • Caroline Donofrio says...

      I’m 5’2″ too! So there is your answer. :)

  37. jan says...

    I love this tradition of buying one new bag every September! What a great way to both budget and treat oneself at the same time.

  38. Rachel says...

    Does anyone know if the crossbody pouch would fit a kindle paperwhite along with a wallet and phone? Ive been trying to figure it out all day….

  39. C. says...

    one of each

  40. LEAH says...

    Caroline, where did you find your amazing sandals???

    • Caroline Donofrio says...

      Thank you! They’re Birkenstocks, but sadly they’re a limited edition style from a couple years ago.

  41. Mikaela says...

    The bags are great, but what is that amazing nail polish she is wearing?

    • Caroline Donofrio says...

      It’s called Happy Wife, Happy Life, and it’s by Essie.

    • Lindsey says...

      Omg. Happy Wife, Happy Life is THE BEST red. Every time it’s on my fingers I feel like a combo of Audrey Hepburn, Jennifer Garner during her Alias days, and Michelle Obama. In other words, an Elegant Badass Queen. Anyways, haha. Sorry to go off on a tangent, Caroline. Loved this post! 💃🏼

  42. hali says...

    Ahhh I love Cuyana! I remember when they opened in Venice and I’d go in quietly to look in awe at their beautiful pieces. I’m laughing at myself for commenting early on two posts with my continued weird phone-wallet enthusiasm… but… if Cuyana made a phone-wallet I’d absolutely purchase one! I’m assuming someone at the company will be reading this post? Apple’s case colors aren’t awesome, but I liked that they were leather and seemingly well made so I went with their passable but slightly awkward shade of pink since they didn’t have a normal saddle leather option. PLUS, if Cuyana made a phone-wallet, it would officially be a cool accessory, which would be a bonus. They have beautiful small clutches and pouches, but the magic happens when the cards and cash combine with the phone in a pocket-sized situation. I know it’s almost fall now so it’s time to pull out purses for carrying scarves and warm things on the east coast, but in southern California we have at least 2 more months to wear slide sandals and go hands-free!

    • jamie says...

      I am desperate for this as well! Especially if it has a strap like the Bandolier phone wallets. NEED!

    • Debbie E says...

      I’m with you! What I wouldn’t give for an iPhone wallet to go with my Guyana tote …

    • We’re listening! I will pass along the feedback to our product team.

  43. Vivian says...

    These bags are so beautiful! Love.

    I’m going to be shopping for a new winter coat this year – can I put in a request for a winter coat feature? (For those of us ladies who live in snowy climates!)

    xo

    • Ashley says...

      Yes to this! Also in the market for a new winter coat (that is cute but also blizzard-proof).

    • Amanda says...

      Just my two cents about winter coats–
      I just bought my winter coat from Zappos about a month ago! Did I feel kinda crazy buying it while it was 90+ degrees outside? Yes. Did I feel awesome paying only $150 for a North Face down parka? Hell yes.

      I have an Eddie Bauer that has gotten me through two -13 Chicago winters so far and has held up well. AND I’m just now replacing my JCrew Factory long puffer that I bought in 2014!!

  44. Erin Beveridge says...

    I have had my Cuyana Burgundy tote for YEARS and I love it!!! It holds everything and I use it everyday for work/life. It has worn in so nicely and looks even better with age!

    Once I even spilled a whole Hydro Flask filled with tea inside it (nightmare)…while in a moving car. Immediately pulled over, dumped my purse on the sidewalk… and it survived and wasn’t damaged at all!

  45. Amanda says...

    Purchasing a new backpack was always a favourite tradition. When I was a kid, my aunt used to always bring a few new backpacks with some school supplies to the office at my school, intended for the kids whose families could not afford supplies for the new school year, and may have come to the school to request some assistance. For the first time this year, I will renew this tradition and drop off a bag with supplies to a local school.

    • Rez says...

      What a sweet and thoughtful gesture. I feel inspired to do the same!

  46. Sara says...

    I have had my eye on their work satchel for awhile! I love their products.

  47. Ansley Clark says...

    Yes, the bags are great, but that outfit though! That dress! That lipstick! Caroline looks fabulous.

    I gather that the dress is Cuyana, too, but where is the lipstick from?

  48. Amy says...

    Nice tuneless bags but that dress looks A+ on you caroline. I hope you got to keep it!

  49. meli says...

    Wise, stylish, boss friends,
    I love a good tote but am perpetually on the hunt for a bag that will look good and put in the work for my professional life. I’m talking big enough to hold it all (laptop, notebooks, subway ride mags and books) but small enough that i don’t look like I’m carrying EVERYTHING. Pockets! with zippers! A bag that actually closes on top ie that I can squish under my feet on long flights or stash away in overhead without fearing that my beloved pens and lipsticks will slip out. Would love to know, what do you guys use?!

    • Ali says...

      Looks like it’s only available in this blue, but I’ve been very happy with this bag. Fits pretty much everything I need for life/work – but doesn’t look like too much. I frequently get complements on it despite it looking very basic.

      https://www.solesociety.com/jeanine.html?color=midnight&size=one-size

    • Heather says...

      After many, many years of looking for the perfect work tote, I found this:
      https://www.bookhou.com/collections/tote/products/carry-veld
      It’s light (made of canvas rather than leather), it’s roomy enough to fit all my stuff, and it zips closed. It has an internal pocket, a durable base of waxed canvas, and a cross-body strap. The canvas does start to fray after a couple of years of hard wear (I’m talking daily commutes on the bus and train in all sorts of terrible Boston weather), but it’s surprisingly durable, and the print is neutral but adds some visual interest. Oh, and it’s handmade by a small Canadian company! Highly recommend.

    • Zoe says...

      Meli, have you checked out Lo & Sons? I just bought the Catalina Deluxe Tote (discovered via this blog!) but it’s more of a travel bag (FTW suitcase handle sleeve!!!!) They have a bunch of other options that could be exactly what you’re looking for: https://www.loandsons.com/pages/womens-laptop-totes-shoulder-bags

    • Madie says...

      Definitely check out Bric’s, the Italian luggage company out of Milan. They’re incredibly durable, nice leather straps, lightweight, with strong zippers. My last shopper tote (X-bag Sportina) lasted for FIVE YEARS of every day use, including commuting on BART! I’m a huge fan. They have lots of options!

    • Madie says...

      Also, have to say that Cuyana’s Medium Caryall Tote looks to fit the bill beautifully! Big enough for a laptop, zipper closure, zipper inside…. WANT. :)

    • Meg says...

      Meli, I use the Lo and Sons OMG bag for this. I originally bought the OG bag from them and returned it because it was too big – something I literally thought impossible because I’m always carrying so much crap. I use it everyday for work and commute on the bus, and it holds my packed lunch, usually a change of clothes for the gym, my kindle, a sweater, etc. I’ve been super happy with it and I think it looks chic too.

    • Anne says...

      Another brand altogether but you may like the Midi Tote from Dagne Dover. A few colors are on sale right now!

  50. Becka says...

    Omg first of all, the comparison to a gourd had me laughing aloud. Second, that circle bag! I’m in love.