It is a fact, well known and uncontroversial, that most men will at some point in their lives encounter the modern scourge that is wheeled travel luggage. Don’t get us wrong, luggage with wheels has its uses: it makes transporting large quantities of belongings easy; and often provides excellent protection for fragile cargo such as camera lenses or objets d’art. However, it doesn’t exactly scream “the spirit of travel”; especially in circumstances entailing a quick getaway or a weekend sojourn to the country.

Ideally, the act of travel should be a stylish and romantic one; and as David Coggins (author of the New York Times bestseller Men and Style) astutely observes “there’s always a time in a trip going up a bridge, across cobblestones, hurrying to catch a train, when you’ll wish you packed lighter and wheel-free”. Put that advice to good use with 8 of our favourite travel bag designs: made to accommodate a lightweight and smartly edited wardrobe that you can sling over your shoulder at a moment’s notice.

1
Bennett Winch weekender

We’ve mentioned Bennett Winch in passing, but it bears repeating that this English bag maker is producing some of the most ruggedly handsome travel luggage on the market. The brand’s poster child is the Weekender: a contemporary take on the classic zipper-top duffle, made using 24-oz bonded canvas and military grade webbing. Conceived with the serial traveller in mind, the Weekender is sized for a 72-hour sojourn, complete with two isolated waterproof compartments and a padded internal laptop sleeve. Available in five colourways, the olive drab is our favourite, pairing extremely well with denim and workwear.

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2
Bottega Veneta leather trimmed printed suede holdall

Under the stewardship of Mr. Daniel Lee (formerly head of Ready to Wear at Céline), Bottega Veneta has doubled down on material innovation with designs like this printed suede holdall. Perfect for the couture-loving jet setter, it harmonises a variety of decorative techniques like suede printing (evident in the blue, black and red “racing stripes”) and intrecciato, the twist-weaving of leather which has been a Bottega Veneta specialty since the 1960s. For a travel bag which is as handsome as it is bottomless (this holdall has a 40-litre capacity) this is a strong contender.

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3
Filson medium rugged twill duffle

Hedonists often tout the tactile pleasures of calfskin leather, but permanent satisfaction comes from robust dependability — a fact that’s particularly true of travel bags. For weekend warriors whose adventures take place off the beaten track, Filson’s rugged duffles have long been a secret favourite. Manufactured using water-resistant twill and decorated with rust proof trimmings (i.e. zippers, snap fasteners), “this Made in America” staple has been delighting travellers for decades. With Filson’s famous lifetime guarantee, every repair is an opportunity to add character to this already robust and outdoorsy design.

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4
Frank Clegg signature travel duffle

Nowadays, it’s common to find travel luggage that does everything short of checking itself into the overhead bin; yet it’s seemingly impossible to source a classically styled duffle made of handsome materials. That’s where Frank Clegg Leatherworks comes to the party. Operating out of Fall River (Massachusetts), Frank and his sons craft beautiful handmade duffles that are bound to instil a sense of knowing satisfaction in owners. Their flagship travel duffle features a hand cut leather construction, generously sized body strips (said to have been inspired by log carriers) and edge stitching that’s executed with painstaking precision. Our favourite version is made up in harness belting leather: a faintly glossy material that will develop a unique patina with years of use.

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5
Louis Vuitton Keepall Bandouliere 50

For the urbane traveler who’s more likely to spend his weekends on a staycation, the Keepall 50 is a comprehensive solution to storing a (long) weekend’s worth of essentials. Travel is a reference point that is inextricably tied up with the Louis Vuitton identity; and this season the iconic Keepall gets the “stealth wealth” treatment with an eclipse leather construction. The infamous LV monogram is deployed sparingly, visible only in the Keepall 50’s fastener, name tag and body strips. Soft sided and cleanly detailed, this is the kind of Louis Vuitton product that reminds you why the house ascended to global dominance in the first place.

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6
Porter short weekender

Though you might balk at the very notion of a luxurious nylon bag, Yoshida Kichizo — founder of Japanese label Porter — has been making quirky, practical travel accessories out of the stuff since 1962. Naturally, a collaboration with Monocle was inevitable, resulting in the creation of the short weekender. Consummately embodying the philosophy that form follows function, this bag integrates two detachable extras in the form of a tote and pouch (for separating toiletries and smaller items). It’s doubtless true that there are more sumptuous looking travel bags out there, but it’s worth the small sacrifice in aesthetic for the immense functionality that’s hardwired into this bag.

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7
M/S suit carrier

Handsome though they are, numerous bags in the duffle/weekender category require a kind of restraint when it comes to packing for the real world. For those who’ve ever had to supplement their luggage with a coat bag, Mismo’s suit carrier is a nifty new take on the format. Manufactured from tight woven army canvas, it incorporates a large exterior pocket (for footwear) in addition to two internal compartments. Users can maximise carrying capacity as Mismo have sized it to hold up to three total outfits — way beyond the norm for your run of the mill garment bag. Our certified pick for those weekend getaways requiring a dose of formality; whether it be weddings, black tie or simply an occasion well suited to tailored clothing.

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8
Stoffa "003" weekly carryall

If one were to envision a travel bag inspired by the philosophy of mid-century modernists (e.g. the Eameses or Richard Neutra) there’s a good bet you’d end up with a product like the 003 carryall. Defined by clean lines and end-to-end symmetry, the 003 combines Stoffa designer Agyesh Madan’s understated taste with technological proficiency. The outer is composed of Tuscan calfskin, treated with a proprietary dyeing process emphasising depth of colour and natural variation. The guts of the bag meanwhile are reinforced with biodegradable polymer; and include two large detachable wallets made to store travel documents and valuables. Spacious enough for a weekend’s worth of clothing for two, the 003 is a chic (and gender neutral) addition to your travel luggage quota.

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Randy Lai
Editor
Having worked in the Australian digital media landscape for over 5 years, Randy has extensive experience in men's specialist categories such as classic clothing, watches and spirits. He is partial to mid-century chronographs and a nice chianti.