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Marcus Kirby
by Published on October 8, 2019

Standing in the middle of the handbag section of a department store while dreaming about the fanciful silhouettes in the new-in section is one of my favorite pastimes. Yes. I’m Bobby, and I’m a bag addict. What can I say, there’s something that feels so good about punctuating a perfect outfit with a flawless satchel. But alas, while I may want every luxury carryall I see, my budget does not allow for it. Sure, I’m all for the under-$100 picks out there, but given my desire for designer from time to time, I make it a point to save for a few seasons to invest in that silhouette I really covet.

But I don’t just drop cash on any old luxury pick out there, I often crunch the numbers to ensure said style has a strong enough cost-per-wear value (dividing the original price by the number of times you wear an item). As in, I want to ensure I would wear the bag enough (thanks to its timeless nature) to get the best investment out of it. Believe it or not, I’m not alone when it comes to abiding by this shopping logic. My fellow Who What Wear editors also believe in the cost-per-wear model.

I tapped some of them to share the top designer bag they’ve bought that has the best cost-per-wear-value. From a Louis Vuitton clutch that comes to about $2 per wear to a work and travel tote that’s held its value over time, these are the handbags worth trying if you’re looking to invest in something new. And of course, if you’re not quite ready but want a just-as-stylish bag option, I also rounded up more affordable picks that will make the same fashionable statement.

"I've carried this tote to work every day for the past two years (and to interviews and internships prior to that), and when I fly it's usually my carry-on bag. I love that it's polished, has a subtle logo design, and fits a surprising number of things. Since I've owned it for going on four years and have been using it daily for the last two, and it was roughly $1300 at the time, the cost per wear is somewhere near $5, but I'd guess even lower than that." — Anna LaPlaca, Assistant Editor

"I bought my Loewe puzzle bag about four years ago, and it's still one of my favorite purses of all time. I have been wearing it pretty regularly ever since and, if I remember correctly, it was around $2000 at the time. If let's say, I wore it at least once a week over four years (though I've probably worn it even more), that would make the maximum cost per wear a little over $9." — Nicole Akhtarzad Eshaghpour, Market Editor

"I bought this bag in Paris over a decade ago, and it's still one of the best purchases I've ever made. I tend to save my money for investment pieces over trendy items and had considered the purchase for years before I made it. I use it at least twice a week, meaning that the cost per wear comes out to under $5." — Kristen Nichols, Managing Editor

"This isn't really an 'It' bag anymore, and I've owned it for several years, but I still just love it. The strap reminds me of a chain necklace and I often carry it at night when I want something a little dressy that isn't as petite as some of my other fancy bags. I've had it for around four years and carry it a few times a month, so I'd put the cost per wear at around $7.50 or less at this point." — Allyson Payer, Editor

"If I remember correctly, I paid $425 for this Louis Vuitton pouch about four years ago. While the price seemed insane at the time, it’s actually one of my best purchases because I use it on the regular. Yes, it was initially intended to hold toiletries, but the clean, structured silhouette makes it perfectly acceptable to use as a clutch for nights out. I also use it for travel to store all of my essentials. I’ve probably used it at least once per week (legit throw it under my shoulder every weekend) since I bought it, which would make the cost per wear just a little over $2." — Bobby Schuessler, Market Editor

Come on, if it works for Kendall Jenner…

You’ll make an instant statement toting around this sophisticated satchel with the mix of tones and textures.

Go on, invest in the trend—mock-croc with a chunky chain—all fashion girls love.

The baguette silhouette continues to reign supreme amongst the style crowd.

Consider this pink dream as an alternative to your basic black crossbody bag for a night out.

So incredibly sleek for that 9-to-5 life.

You can never go wrong with a classic bucket bag.

Wear this stunner as a crossbody while you’re running around, or remove the strap to use as a boxy clutch.

Need a new travel or work tote? Consider this spot-on (wink, wink) style.

Say hello to the perfect black crossbody.

Fit all your main essentials in this sleek bowler bag.

Next, check out some of the biggest handbag trends of fall 2019.

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