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A Gentleman’s Guide

The New Rules of Bags

The look of backpacks, briefcases and holdalls is changing. Here’s how to stay current and stylish


We live in enlightened times. When it comes to dressing with style, the modern gentleman has a far greater sartorial arsenal at his disposal than ever before – and nowhere is this more evident than in the rapidly expanding market for men’s bags.

There was a time not too long ago when it was deemed inappropriate for a man to carry his belongings in anything other than a briefcase, backpack or an overstuffed wallet. Anything designed for looks as well as functionality was condescendingly referred to as a man-bag, and anyone who dared to carry one was regarded as fair game for ridicule (remember that 1999 Friends episode, “The One With Joey’s Bag”?).

Such opinions are now laughably outdated. Whether it’s down to men coming to terms with the need for a practical solution to the very real problem of how to transport more than just their keys, wallet and phone — or just a greater general interest in looking good — it’s clear that the bag is now not only an accepted part of the male wardrobe; it’s an essential part of it. With that in mind, we’ve prepared a gentleman’s guide to bags, and how to carry them off with style.


  • IMAXtree

When people talk about man-bags – in the narrow-minded, derogatory sense – they’re usually referring to totes. Perhaps it’s because they’re designed to be held in the hand, and therefore bear a superficial resemblance to a woman’s handbag. This is nonsense. As the example in the shot above shows, modern tote bags can be a decidedly masculine accessory. Cut in cotton canvas and fitted with dark brown leather features, this one has a rugged, utilitarian feel to it, and its subdued colours work particularly well with denim. Follow this man’s example and hold yours in your hand. Don’t sling it over your shoulder – the handles of a tote bag are rarely long enough to put your arm through – and try to resist the urge to rest it in the crook of your arm.

  • RRL Dayton Leather-Trimmed Cotton-Canvas Shoulder Bag

  • Porter-Yoshida & Co Leather-Trimmed Piqué Tote Bag


  • Guerreisms

Do you still associate the backpack with your school days? With memories of kicking through leaves in grey flannel shorts, weighed down like a packhorse with textbooks? It might be time to let go of your preconceptions because the backpack has grown up. This new breed puts style and functionality on an equal footing, combining hands-free practicality with clean, modern design. Take this sleek one from Danish accessories brand, Mismo. It owes something of a stylistic debt to the mountain packs used by the Swiss Armed Forces in the 1950s, but it’s designed for the man about town. But if you’re planning on wearing it over a suit jacket, make sure it’s an unstructured one. We don’t recommend wearing a backpack over your best business suit, as it will compress the padding in the shoulders, and look a little awkward.

  • Miansai Harbour Canvas and Leather Backpack

  • Mulberry Leather-Trimmed Canvas Backpack


  • Guerreisms

Just as traditional work attire has become more relaxed over the years, so has the shape of the international symbol of the working world: the briefcase. We’re so taken with this softer silhouette that we’ve decided to name it as one of the season’s biggest trends. It was embraced by a number of influential designers for fall, such as Thom Browne, Balenciaga and Berluti, but if you want our opinion – there’s no better way of buying into this trend than with Bottega Veneta, that has been making it for years. The luxury Italian brand’s signature weave, known as intrecciato, makes for a beautifully supple and pliable leather that lends itself naturally to this shape. We’ve shown it here as part of a casual outfit just as a reminder to let go of any notions that briefcases should only be for business, or carried by men wearing suits and ties.

  • Bottega Veneta Intrecciato Leather Briefcase

  • Thom Browne Grained-Leather Briefcase



We won’t beat around the bush. The bag you can see in the shot above is made by Berluti. If you were to buy one today in the UK it would set you back just more than £2,000, while if you live in the US, the asking price is well in excess of $3,000. Without venturing into the market for exotic leathers, you will struggle to spend a great deal more than this on a briefcase. And yet – and we do not say this lightly – it should not be considered an extravagance. Unlike T-shirts, jeans, or anything other than the very best shoes, a good briefcase such as this is built not only to last but to improve with age. If kept well, items like these will outlive you. They might even outlive whoever you decide to pass them on to. When you think of it like that, the price in terms of “cost per use” starts to seem quite reasonable.

  • Berluti Un Jour Venezia Leather Briefcase

  • Berluti E'Mio Leather Briefcase


  • Lee Oliveira/ Trunk Archive

Following on from the previous point, it’s worth remembering that in certain items a little wear and tear is a good thing. It says timeless, tasteful and hard-wearing; it says “investment piece” rather than “throwaway trend”. In this shot, we’re presented with a couple of excellent examples. The waxed cotton field jackets worn by these gentlemen look better for being a little frayed around the edges. And then there’s the handsome leather briefcase carried by the man on the right that bears the visible dents and scuffs of years from regular use. Sadly, this is not the kind of look you can easily ape, unless you have a father or grandfather who is willing to let go of his old briefcase. We can only wait for time to work its magic. Another point that is illustrated here is that while certain items get better with age, others – white jeans, for example – do not. Keep them clean.

  • Lotuff Bridle Leather Attaché Case

  • Dunhill Duke Leather Briefcase


  • Tommy Ton/ Trunk Archive

Keys, wallets, smartphones and the various other bits and pieces we carry around with us can really ruin the lines of a suit. The man in this picture clearly understands that and has removed all essential items – including his umbrella – to this smart leather roll-up folio. This shot in particular demonstrates just how far men have come in accepting the practical advantages of owning bags in a variety of shapes and sizes. Imagine a tote or backpack in a situation like this. It would be less than half-full so you would be carrying around more bag than contents. The folio offers the ideal alternative — one that’s just right.

  • Maison Margiela Vintage-Effect Leather Portfolio

  • Brunello Cucinelli Leather and Flannel Document Case