Style Guide: Frequent Flyer

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When you’re a working professional, traveling from place to place is often a necessary part of your daily grind. For some, this takes on an entirely different meaning, thanks to intercontinental passports, strict deadlines without regard for differing timezones, and red-eye flights to your client’s base of operations. Obviously, wearing a suit for the entire trip is outside the realm of sanity — so, you’ll need to find something a bit more comfortable to make the journey.

While a full-fledged professional getup might not be the answer to all of your traveling qualms, there are a handful of stylish garments that can optimize the way that you pack for your next big trip. Whether you’re looking for clothing that can keep you comfortable and non-confined during your flight or an ensemble that can transition from formal business to after-hour activities with ease, our Frequent Flyer guide will give you a glimpse into the world of the stylish circumnavigator.

Dockers Alpha Chino

Dockers® Alpha Chino might be a refined, professional-approved pant for the workplace, but that doesn’t make it any less appealing for the avid traveler. In fact, the cotton and elastane-imbued peripherals come standard with the company’s Smart 360 Flex™ four-way stretch fabric — an innovative material that was tailor-made for those who are constantly on the move. Whether you’re heading outdoors for a day in your favorite downtown area, or to a board meeting for your new job, these smart, stylish offerings have everything you need to round out your handsome image, including hidden security-zip pockets, single-welt button-throughs, a coin catch pocket, and a clean-finish hem that promotes fashionable functionality.

Purchase: $78

Stance TIGRIS Socks

Stance’s genre-defining socks are the standard by which every alternative offering must abide, and the company’s TIGRIS dress socks are no different. These aesthetically-pleasing socks are imbued with cotton, elastane, polyester, and nylon, giving them a durable composition that’ll last over the course of many paces — perfect for the avid traveler who relies on his feet to take him to the world’s most sought-after locations. Vivid toecap and heel colorings pair with the sock’s duplicated tiger’s head graphic, creating a contrasting, but subtle palette of sharp hues on its shadowy backdrop.

Purchase: $15

Buck Mason Double Weave Vintage Shirt

Buck Mason’s heritage menswear is always a solid choice for any outfit, but when speaking on the perfectly-prepared traveler’s wardrobe, the Double Weave Vintage Shirt is unparalleled. This ultra-comfortable button-up is a cotton-imbued garment that you can wear under most of your professional attire, while also being able to transition into after-hours activities with ease. And thanks to the shirt’s double-weave woven gauze fabric, you’ll never have to worry about that claustrophobic feeling you might get in other, less versatile shirts, thanks to a breathable, loose-hanging silhouette.

Purchase: $105

Bellroy Travel Wallet

If you’re heading from port to port, you’re going to need something for all of your important documents. Luckily, Bellroy already has you covered with the aptly-named Travel Wallet — a contemporary accessory that’s been built specifically for globetrotters. Inside of the wallet’s premium vegetable-tanned leather exterior, you’ll find a selection of compartments where you’ll be able to house your passport, plane tickets, paper items, or other important documents, while still retaining the composure of other high-end holders. Better yet, a refillable micro pen can be found within the Travel Wallet’s bifold, freeing up pocket space, and allowing you to fill out and sign paperwork while on-the-go.

Purchase: $120

Aer Flight Pack 2

If you’re traveling for work, but don’t want to betray your urban roots, it might be a bit difficult to find a backpack that can fulfill both sides of the niche. That’s where Aer’s Flight Pack 2 comes in. This comfortable, everyday-carry peripheral was designed from the ground up for professionals who find themselves hopping on a plane consistently, calling upon an adaptable silhouette, a 1680D Cordura ballistic nylon construction, and YKK zips to create a versatile performer that can be utilized as a shoulder bag, backpack, or briefcase via a suite of bespoke handles. Inside, you’ll find a plethora of pockets to keep all of your important accessories organized, making the Flight Pack 2 the perfect companion for any avid traveler who’s looking to keep his carry-on stylish, but purposeful.

Purchase: $160

Grenson Curt Leather Derby Shoes

Tying together a professional outfit can be difficult, especially when you’re trying to straddle the line between formal and fashionable. Grenson’s Curt Leather Derby Shoes are here to help you with that problem, pairing long-lasting durability and renowned construction with a selection of premium attributes like black calf leather, Goodyear-welted rubber soles, and an attractive lace-up closure to keep things looking great. Plus, with over 200 individual steps and eight weeks of production time for each shoe, you can rest assured that your feet will be dressed in the finest footwear imaginable.

Purchase: $350

Belstaff Cooper Suede Blouson Jacket

Wearing a button-up and chinos for your next big trip is all fine and well, but you’re always going to need something to pull that upper torso together. Belstaff’s Cooper Suede Blouson Jacket is the perfect way to accent your favorite base layers, thanks to its rugged, biker-inspired exterior that references renowned retro styles from the 1950s. On its exterior, a supple suede material joins with the jacket’s metal eyelets and waist tabs to give the garment an undeniable vintage aesthetic. Snapping fasteners and a throat latch engraved with minor detailing round out the fashionable top layer.

Purchase: $995

Longines Aviation Bigeye Pilot Watch

Longines’ Aviation Bigeye Pilot Watch is the perfect wrist-worn companion for any traveler, and not just because of its history in circumnavigation. This cleanly-tailored, aviation-style chronograph is as handsome as they come, calling upon a sleek stainless steel case, brown leather strap, and black dial to create the perfect contrast of vintage colors. Three individual sub-dials, an L688 automatic movement, and a 54-hour power reserve ensure that the watch remains accurate and precise throughout your travels, allowing you to focus on sights and scenery instead of punctuality.

Purchase: $2,625