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

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