I’m in a bit of a bag predicament, and since I’ve exhausted my family and friends enough on this matter, I thought I’d pose the question to all of you. I’m in need of a new bag for nights out, and I need help deciding if I should splurge on the Saint Laurent Medium Monogram Satchel or the Chanel Boy Wallet on a Chain.

Not only do I have a deep love for all kinds of bags, but I’m becoming smarter about my bag purchases. I’m buying less frequently and saving to buy investment pieces that are classic, yet still speak to my personality. I also, however, want to diversify my growing collection. My main criteria for the bag is that it’s black with silver hardware and that I can wear it across my body–the days of holding a drink or a cellphone in one hand and holding a bag with the other are long gone.

Let’s start with the Chanel Boy Wallet on a Chain. I own a Chanel Classic Flap, and as much as I love Chanel, one thing particularly bothered me about the WOC, as it’s called by Chanel fanatics. Maybe I’m just being picky, but for the money I’ll be spending, I was very disappointed that the closure of this bag was just a snap button. I was expecting the same lock that is on the Boy Bag, or at least a magnetic button. Not only that, but when I tried this bag on and put my stuff into it, trying to close this bag wasn’t easy. The bag itself is beautiful, though, and I know I would wear this bag as a crossbody, a clutch and occasionally as a wallet. It’s definitely versatile, but I don’t know if I can deal with a snap closure that will be a pain to close.

As for the Saint Laurent, I never thought I would find myself contemplating one of the brand’s bags, yet here I am, lusting over a brand that usually feels like nothing special to me. There’s just something about this bag I can’t get out of my head. The beautiful python-embossed leather, the nostalgic feel, the tassel and the beautiful plated logo are enough to make me swoon. The bag is a perfect size; it’s not so small that it’s a puzzle to fit everything inside, nor is it so big that it looks ridiculous on my petite frame. The closure is magnetic, so it’s not as troublesome as the Chanel, and it’s a beautiful bag I can also see myself wearing both now and in years to come. It has the staying power that I’m looking for while still being aesthetically pleasing.

Deep down, I think I know which bag I’m leaning toward, but I would love to hear your thoughts, input and any other suggestions you may have in the comments!

Saint Laurent Classic Medium Monogram Tassel Satchel in Black Python Embossed Leather
$2,290 via Saint Laurent

Saint Laurent Classic Medium Monogram Tassel Satchel in Black Python Embossed Leather

Boy Chanel Wallet on a Chain
$2,400 via Chanel

Boy Chanel Wallet on a Chain

P.S. Please consider supporting our small, bag-loving team by clicking our links before shopping or checking out at your favorite online retailers like Amazon, Neiman Marcus, Nordstrom, or any of the listed partners on our shop page. We truly appreciate your support!

Share Your Thoughts With Us

  • KloeF

    I prefer the Saint Laurent. I love the embossed python, but also the proportions for that size a bag (wallet) seem to work better.

  • kk

    I’ve never really liked the boy collection, the quilted pattern and the lines on the borders seem the clash ever so slightly.

  • PJGambler

    Am kind of surprised Chanel closures haven’t improved over the years-the closure is a problem. On my French style Chanel wallet it is the same thing and I end up with change all over the inside of my purse, because the snap won’t stay closed. Have tried to have it fixed professionally, but still won’t stay shut once a few coins are put in it So, for that reason, I’d vote for the Saint L.

  • b

    I like the wallet on a chain but not that style one. Especially because it looks like a boy bag but doesn’t have the closure. I think the ysl bag is so much more classic. Go for the ysl!

  • justa9url

    I’m in a similar predicament as of late but I think you should go for the Saint Laurent one seeing as you already own a Chanel Classic Flap and never thought you would choose a Saint Laurent bag of any sort.

    • Katherine Callaghan

      Agreed! Like I said, Chanel is my favorite brand, but now that I own the Classic Flap, every bag I look at from Chanel just doesn’t compare,

  • AV

    I’ve had 2 WOCs that I’ve been using for over a year now AND THE CLOSURE STILL BOTHERS ME. I really, really do not understand why they didn’t use the magnetic closure used on models like the Chain Around?! Despite the troublesome snap closure I still use these bags all the time, I love them and I wouldn’t consider selling them to swap for anything else.

    That YSL is great. I have a YSL embossed croc bucket bag and the quality is so much better than I was expecting. If your cross-body is made to the same standard as my bucket then craftmanship no longer becomes an issue and it’s purely down to aesthetics. And if you’re looking for a night-time bag, in this instance, I’d go for the YSL.

    • Katherine Callaghan

      I’m glad I’m not the only one! The sales representative in the store was looking at me like I was crazy for not liking the snap closure but I know it’ll bother me EVERY TIME I wear it!

  • Definitely YSL. It is so laconic, so elegant. And I love python, real or embossed. It would win vs most other similar matches (ie small black shoulder bags).
    Plus I just cannot warm to the Chanel Boy bag/wallet at all. Even if it was for $24, not $2400.

    • Katherine Callaghan

      I always liked the idea of the Chanel Wallet on a Chain, but after looking at it in person for the first time, I wasn’t impressed.

  • JohnL

    You had a reaction to the YSL while the Chanel wasnt what you were looking for . This shouldn’t be a question…. Get the YSL

  • I think the Saint Laurent is a no-brainer, personally. I would love to have that bag, and I’m not even a particular fan of the brand. The quintessential party girl crossbody.

  • Jimmy Lin

    Bonjour YSL au revoir Chanel … Chanel so overpriced plus their hardwares are getting very flimsy nowadays . that’s all ^^

  • klynneann

    I think you’re leaning toward the YSL and I agree. I have a WOC and love it but there’s plenty of room in it for me – clearly you need a little more and you shouldn’t have to worry about getting all your stuff in every time you want to use it. Plus I’m not a fan of the Boy bags and the YSL is just a little less expensive. Finally, as another commenter mentioned, if you’re not otherwise inclined toward YSL, this is your chance. :)

    • Katherine Callaghan

      Exactly, this is my time to get a YSL bag that I LOVE! Now all I keep thinking about is wearing it out this weekend!

      • klynneann

        Also, just for the record, the YSL really is beautiful! :)

      • Katherine Callaghan

        It really is!!

  • hchlldz

    You should check out Saint Laurent’s Lulu bag! :)

  • dnfl

    Ysl fo sho

  • AAAA

    You clearly want the YSL. If you get the Chanel, the closure will still bother you and you won’t carry it as much. Go with the one you already know you want :-)

  • Katherine Callaghan

    Thanks everyone! You’re all right, deep down I love the YSL and that’s the bag I can’t stop thinking about it. You all encouraged me so much that I think I’m going to buy the YSL bag today after work!

  • shueaddict

    The YSL is sleeker looking and more versatile. I love many Chanel bags and hate plenty of Slimane’s creations of late but in this case YSL seems the savvier choice hand down.

    • Katherine Callaghan

      The more I look at it the more I fall in love!

  • Yazi

    YSL, no question about it.

    • Katherine Callaghan

      Yup, 100%

  • FashionableLena

    There is something about that YSL clutch that’s just sexy.

  • Finem Lauda

    YSL on priciple.

  • Winn

    beating a dead horse here, but another vote for YSL

  • M harbor

    Ysl !!, love the boy but not woc boy!
    Another nice one is the Dior promenade pouch!

  • anon

    It’s great that you’re going for the YSL. It seems like you’re not entirely happy with the Chanel WOC, when you should be-especially when investing in a night out piece. You seem to really like the YSL one more. It shows in the article you wrote, so deep down, you want the YSL:)

  • BagLover

    YSL :)

  • Sara

    This is a lovely choice. Can’t go wrong with this one! Did you you consider the Valentino Rockstud Va Va Voom bag at all? They’re stunners too and would fit your criteria pretty well!

  • ami

    I’d go for a Celine Classic Box Bag if it wasn’t more expensive. Looks like you’re leaning towards the YSL since the Chanel doesn’t work for you that much.

  • Khaya

    Saint Laurent ALL THE WAY!!! Something about that bag screams sexy in a way that the Chanel Boy WOC just doesn’t. To be honest, next to the YSL bag, the Chanel one looks dated and granny-like. I’m in LOVE with that Saint Laurent. Make that purchase!!

    • Katherine Callaghan

      I actually bought the YSL bag last night, I’m in love!

      • Kyoungtae Yoo

        Hello How did you guy the YSL bag online? it’s sold out everywhere..
        can you tell me how I could get them?

  • Mya Wilkes

    I’m definitely late to this party and I don’t believe I’m saying this, but the YSL ALL THE WAY! its a stunner!

  • ellavanw

    Clearly I am late to the party, but to take the minority view: I have the Boy WOC in red caviar and love love love it. It is amazing for travel: lightweight, fits in a larger tote easily, so functional. I’m not sure what you are saying about the closure; the snap closure has never bothered me and I think a larger/heavier closure would be disproportionate on such a small bag. I think the tassel makes the YSL appropriate only for night, whereas the WOC can be used anytime, anywhere. If you are looking for a bag for parties, though, that’s not a factor. Enjoy your purchase!

  • adguru

    You’re definitely leaning towards the YSL and the cheap closure on the Boy bag will drive you crazy.

  • Ava

    Chanel. Besides the Chanel is more wearable.
    Personally the YSL looks like it’s trying too hard.
    The YSL dingle berry hanging looks ridiculous!

  • Molly

    I have a similar dilemma:( I was planning on buying the Chanel classic double flap in black, but this winter, suddenly EVERYONE i know has one!! It’s becoming ridiculous. What should I do? Go for a different colour? Or wait until I can put my hands on a Birkin? Please help. I plan to make the purchase when I’m in London in April.

  • Purseinsanity

    So happy you went with the YSL! It’s one of those bags that i immediately loved when I saw it. I got the black croc embossed one with silver hw recently. Something about that tassel I really love LOL! Congrats!