Valentine’s Day Gift Guide 2024: The Finest Footwear For Travelers

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When traveling means spending long days on your feet, the right shoes are your superpower. Marry performance and luxury, and you can hit the ground running. Gifting an amazing pair of shoes, both fashionable and functional, is a surprise that elevates every traveler’s fashion edits with high marks for ingenuity. Be that person they won’t soon forget: a soul searcher with impeccable taste. Here are ten of the finest footwear for travelers to gift this Valentine’s Day.


The Pilar from INEZ in black
The Pilar ($378) from INEZ footwear is a doozy of a bootie with a four-inch covered heel that also has more than an inch in a covered platform INEZ

All Inez footwear is made in Spain with a distinct point of view: It’s all about wearing heels, comfortably.

There’s some magic in a shoe that puts forth a bootie with a four-inch covered heel that also has more than an inch in a covered platform, and wears like a sneaker. It’s a doozy of a bootie ― a bit of an obelisk, like the monument sitting on the moon in Stanley Kubrick’s 2001: A Space Odyssey ― so peculiar, dramatic and yet chic. The Pilar ($378) is thought by some as the most comfortable heels to travel in. You can traverse the airport with luggage in tow, and you won’t think twice. Fashion tip: wear them with a wide-leg jean.

For those less into heels this high, other wonders from Inez include the Caro ($270) with a two-inch leather stacked heel, which allows for even faster running through airports due to the elastic side gores, or the Carla ($254), another two-inch leather stacked heel that’s sublimely comfortable.


The Original from Amberjack ($189) in Obsidian
The Original from Amberjack ($189) in Obsidian AMBERJACK

Amberjack is a carbon-neutral company, proud to be making men’s dress shoes that are both better for your feet and the planet. Its leather is sourced from an ISO-certified tannery that, according to an interview with Amberjack founder and CEO John Peters in Authority magazine, uses solar power. The shoes are also manufactured in Portugal at a fair wage factory that uses plastic-free and recyclable packaging.

In an email, Peters shared his vision leading men into 2024 with the most comfortable shoe that is also spiffy enough to go from the plane to the boardroom: “Amberjack is all about style AND comfort. There’s a lot of dress shoes out there that look beautiful but kill your feet, and there’s lots of shoes that feel great but don’t look great. Our goal is to make modern, dress-casual shoes for guys who want both. Whether you’re traveling, going to the office, or just meeting friends, our shoes are versatile and look just as good in a suit as a pair of jeans. We think that’s more important than ever in today’s age of hybrid and flexible work. Even as work-wear and fashion trends change in 2024 and beyond, you can never go wrong with comfortable dress-casual!”

Recommended selections include The Original ($189), the most advanced crossover casual shoe, and The Loafer ($179), a sublime loafer made with water repellent Italian suede.

Wolf and Shepherd

The Crossover Victory Trainer from Wolf And Shepherd ($269) in khaki honey
The Crossover Victory Trainer from Wolf And Shepherd ($269) in khaki honey WOLF AND SHEPHERD

Take two former Division I track and field athletes, have them design the best shoe for going from performance to work and back, and the result is Wolf and ShepherdRunning with the bulls in Pamplona and competing in a half-marathon aren’t recommended pursuits for all, but the results speak for themselves. No formal shoes can get you from Point A to Point B in style and comfort faster.

With men in mind, the shoes are designed to be fashionable yet stand up to long hauls. The impressive construction includes Italian leather uppers, the company’s unique flex shank technology to provide structure and arch support, a foam heel compression system to absorb shock, and proprietary memory foam for the footbed.

Top selections from Wolf and Shepherd include the cleverly crafted Crossover Victory Trainer ($269) that expertly marries a foam-injected scuba lining with chic Italian leather trim and the SwiftKnit Derby ($179), their lightest and most adaptable shoe in the portfolio. The designs work beautifully for all-day wear from the 747 to the boardroom.

Scarlett Chase

The Portia Stretch 75 bootie ($625) in Loden Suede.
The Portia Stretch 75 bootie ($625) in Loden Suede features a three-inch heel that you will not even notice when walking because it’s luxuriously comfortable SCARLETT CHASE

Scarlett Chase was founded by Sandra Powers Murphy to own the all-day-wearable heel category for women. Handmade in Italy with sneaker-like construction, Scarlett Chase shoes are designed with the help of orthotic and orthopedic professionals. Made with the skeletal structure of feet in mind, Scarlett Chase shoes combine incredible arch support and a heel stable enough to walk through busy city streets and over sidewalk grates.

They’re also flat-out gorgeous. The Portia Stretch 75 bootie ($625) features a three-inch heel that you will not even notice when walking because it’s luxuriously comfortable. Everyone else will notice their bold design, however.

“Our collection is curated to give women the must-have classics they need to move with confidence and stability. Scarlett Chase is designed to give women their own beautiful power without compromise,” Sandra Powers Murphy, founder and CEO, said via email.


The Camera from Aerosoles ($135) is an incredible day to evening crossover sandal that makes a statement.
The Camera from Aerosoles ($135) is an incredible day to evening crossover sandal that makes a statement. Pictured here in pomegranate AEROSOLES

Always been a popular workhorse of a shoe, Aerosoles are also a fashion brand with many stylish surprises for Valentine’s Day. The Camera ($135) is one groovy women’s platform sandal that feels like you’re walking on air. With a 2 ½-inch heel and 1-inch platform with a standout signature hardware buckle and ultra-fashionable options (like metallic gold leather and pomegranate in suede) this sandal maintains comfort and transitions from day to evening effortlessly.

Jack Erwin

Isla Lug Penny loafer ($238) from Jack Erwin footwear
Isla Lug Penny loafer ($238) from Jack Erwin footwear JACK ERWIN

Manufactured in Spain, Jack Erwin is a true disruptor in the luxury footwear market, making luxury shoes at a price that anyone accustomed to paying thousands for a well-crafted shoe can appreciate. Discerning men will fall in love with the gorgeous Watts ($248) brogue cap-toe oxford, a classic constructed with a calfskin upper, leather outsole and fully leather-lined.

The collection, which went online in 2013, introduced a women’s collection in 2019. A favorite in this collection is the Isla Lug Penny Loafer ($238), which comes in full and half sizes and has a chunky lug sole for extra grip and durability, and the Stella mule ($220), an everyday slip-on with a clean look.

White Mountain

The White Mountain Danny Suede Bootie ($99, now on sale for $59.99) pictured in navy suede
The White Mountain Danny Suede Bootie ($99, now on sale for $59.99) comes in black suede, navy suede or natural leopard suede WHITE MOUNTAIN

White Mountain will ensnare you with its price and keep you forever with its incredibly comfortable shoes. Understated, functional, and elegant, White Mountain offers top selections like the women’s Being Leather Clog (regularly $89.99, now on sale for $49.99) and the Danny Suede Bootie (regularly $99, now on sale for $59.99). Both are great selections for zooming through airports all day while looking on-trend.


The Maguire Napolli Black Loafer Penny Loafer ($240), pictured, is a wardrobe stable.
The Maguire Napolli Black Loafer Penny Loafer ($240) is a wardrobe staple that is both fashionable and affordable MAGUIRE

Getting the highest quality shoe doesn’t always mean paying a premium. Sisters Myriam and Romy Maguire married quality and affordability beautifully with the Maguire shoe brand. Their direct-to-consumer model mirrored that of Warby Parker and Harry’s, giving footwear aficionados a new way to shop.

From about the 1940s to the 1960s the penny loafer was a hit on college campuses ― made even more famous by Elvis, Miles Davis, James Dean and former President John F. Kennedy, among many noteworthy names that rocked the loafer. Just in time for Valentine’s Day, Maguire is featuring the Napoli Back Loafer Penny Loafer ($240) with a twist, a little red heart atop the loafer with visible stitching in four color options: black, tuxedo, bordeaux and lipstick.


Thursday boots are the ultra cool-looking, go-anywhere, anytime boot that offers the comfort of a sneaker. You can wear them all day, and dress them up or down. They come in so many cloth options, they can be more casual or more fancy depending on what you choose. The rugged and resilient feel gives them an edge over many of their contemporaries.

Fan favorites include The Chelsea (starting at $160) boot in many different styles and heel stacks, with a signature flexible elastic goring for easy on and off. The Legend ($168) platform heel has a two-inch heel with an edgier look and feel.


For a kick of fun and whimsy with incredible durability and comfort, Sorel makes a trend-setting shoe that marries boot style and sneaker style with pops for bright colors like Optimized Orange, Red Gio and Vintage Pink.

Popular styles include the Out N About Slip-On Women’s Wedge ($77.92 – $130) with a 1 ¾-inch heel with a ½-inch platform ― ultra-comfy and durable year-round ― and the Caribou X Women’s Waterproof Shoe ($89.92 – $150) with a 1 ½-inch heel and 1-inch platform. Their summer wedge sandals are super vibe-y, like the Cameron Flatform Puff Wedge Mule Sandal ($64.92 – $130) in Koi.

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