There’s a famous Seinfeld subplot where Jerry, tired of bulky wallets, starts carrying what he insists is not a purse but a “European carryall.” He’s ridiculed by the rest of the crew around him — and eventually has it snatched by an actual purse thief.
Turns out Jerry might’ve been ahead of the curve. In 2025, hardly anyone would blink.
Designer bags have been the highlight of many red carpet and NBA tunnel fits as of late. Jacob Elordi carrying a large Bottega Veneta tote, Pedro Pascal has carried a black leather bag on numerous occasions, while The Summer I Turned Pretty’s Christopher Briney has gone slimmer rocking a small clutch with a gold chain. Timothée Chalamet, now the face of Bleu de Chanel, has been going beyond fragrance, often wearing Chanel crossbody bags and other accessories like scarves and folding them seamlessly into his outfits.
Even the Indiana Pacers’ Tyrese Haliburton is known to carry The Row’s Margaux tote. Suddenly, men are openly embracing leather totes and small “purses” that borrow from the ladies.
A quick look at your social feed will find creators and influencers trying the look.
Toronto-based creator Sam Bolianatz grew up around big bags — his mother always carried one, even through the mini-bag craze — and he remembers slipping her tote over his shoulder once or twice. That small moment stuck, and eventually he went looking for one of his own.
Now, he sees the oversized tote as an easy way for men to add texture and colour to an outfit. “I also love using a bag to change the overall vibe of your outfit. Pairing a chic structured bag with a casual look or choosing a more practical bag when you’re dressed up is always interesting to me, “ he says.
Part of the appeal, he admits, is practicality — his style has always lived at the intersection of comfort, function, and aesthetics — but it’s also about proportions. “I always feel a bit silly with a small bag but more confident with a sleek large tote,” he says.
A tote is naturally functional, sure, but these celebrities are also being deliberate about it. They’re choosing silhouettes that soften the look, add movement, or create contrast with sharp tailoring. And they’re inviting the question: what’s he carrying in there?
As menswear leans toward louche tailoring, a big, slouchy leather bag taps into the same mood. Runway shows of late have been signalling the oversized leather tote’s moment. At Bottega Veneta’s Spring-Summer ‘26 collection, for instance, the first-female creative director wove the house’s signature Intrecciato leather into large-form bags and dopp kits that balanced masculinity and refinement. The same for Louis Vuitton Men’s with smooth leather bags in non-monogrammed forms — totes and slouchy shoppers included — walked down the runway as part of the narrative of quiet luxury and utility. Together these moments underscore how the “bag-as-accessory” for men has moved beyond novelty into wardrobe staple territory.
Bolianatz is already eyeing the next evolution. Michael Rider’s first collection for Celine is starting to hit stores, and the New Luggage bag has his attention: a supple lambskin tote he says he’d use both daily and as a weekender.
Whether it’s a structured designer tote, a floppy vintage leather shop or a small clutch, men are realizing what women have known forever: the right bag changes everything.
Louis Vuitton Men’s Keepall Bandoulière 25
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Crafted from Monogram Surplus coated canvas in a soft khaki green, this Keepall Bandoulière 25 gives off its own sort of military chic vibe, carrying the form of a full-sized duffel that has been shrunk down into a compact package. Whether carried by its leather double handle or over the shoulder using its detachable shoulder strap, the standout bag is just big enough for one’s daily essentials. ($3,550)
Dior Small Rider Soft Hobo Bag
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This isn’t the first time we’ve obsessed over the Dior Oblique Jacquard pattern that’s been circulating through the brand’s collections, and it certainly won’t be the last. You may remember it from the B57 Low sneakers we were so excited about last fall? Either way, pairing the iconic pattern with the simple practicality of the Rider Soft Hobo Bag is a win in our books. ($3,100)
Chanel Boy Chanel Handbag
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First launched by Karl Lagerfeld for the Fall-Winter 2011/2012 ready-to-wear collection the BOY CHANEL handbag takes inspiration from the hunters’ cartridge bags that Mademoiselle Chanel would wear over her shoulder. Its classic construction is contrasted by the use of heavy curb chains, and the whole package comes together in a refined androgynous package, blurring the masculine-feminine lines as Chanel loves to do. ($9,850)
Jerome Manguba Title Bag
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Turning eyes back to Canada for a moment, we’ve been especially impressed by some of Jerome Manguba’s recent creations, including his new Title Bag. Its form blurs the line between tote, purse, and messenger, and its soft cowhide construction reads almost like a well-loved vintage piece, without seeming overtly “distressed”. It’s a great foray into the bag space, and we’re eager to see what comes next. ($750)
Hermès Horseback Bag
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Yes, we opted for green again, but can you blame us? This messenger-adjacent design pulls inspiration from the equestrian world, with a quilted Woolycot canvas pattern that mimics a horse’s saddle pad. Unlike some of our other selects, the Horseback Bag does what Hermès does best; it’s a statement of quiet luxury, blending into an outfit rather than calling for attention. If you’re looking for something even more subtle, it also comes in black. ($7,550)
