Just by making simple fashion decisions, you can boost your self-esteem, make you more productive and improve your career opportunities. Every week, I help 1,000+ men make the most of their wardrobe with fashion tips to upgrade your life.
I’m not a frequent visitor to the Alps, the Riviera, nor any resort, but I follow a bunch of guys on social media who are.
Style writers, clothing brand execs, bons vivants, the sort of fashion-focused men who might be turned away at the Cannes film festival because their pink and gold jacquard jacket violated the subdued dress code.
Although I enjoy having a look at these looks, my modest wardrobe budget simply will not allow such extravagance.
Jet set attire? More like… best get a new tire (Seriously. This summer all my clothes-money has been funneling into a series of unfortunate car repairs).
I still value dressing thoughtfully, despite my limited fun-funds, I shan’t be seen touring a historic downtown in a low-effort t-shirt and cargo shorts.
And I certainly would never allow myself to board a plane in sleepwear, which is so prevalent to the point that it’s tiresome to even complain about.
In my view, t-shirts are pajamas (except in the few situations they aren’t).
Wealth is not a prerequisite for dressing sharp on vacation.
Truly, the stylish traveler needs only a few visits to the thrift store and a little curiosity. But, where can a fella look for guidance?
It’s easy to find travel advice articles published in the established style magazines.
These typically recommend packing a sparse and simple wardrobe: Blend in. Wear neutrals. Build your clothing capsule in monochrome.
This is a seductive path to looking nice, but it’s an expected and well-trodden sort of nice.
The style notables of social media might offer more individual takes on travelwear, but it might be more interesting to look to the professional travelers.
Hosts of television travel shows are experienced in dressing in a functional and appropriate way, and as showmen they know their outfits are on camera, reaching countless viewers.
Let’s consider my favorite three hosts:
I’m a longtime fan of Rick Steves’ Europe, hosted by the most cheerful of travel personalities.
Aiming to motivate America’s least-confident world travelers, Rick suggests an entirely practical approach to vacation-wear: bring as few items as possible and stick to neutral colors.
This über-casual approach offers only one tip approximating formality: don’t wear shorts.
In thirty years as host Rick himself has exemplified unfussy middle-age suburban dad style: jeans or chinos, a polo shirt, and comfortable sneakers (hiking boots if you’re strolling the Alps).
Nearly every episode is filmed in spring or summer, so Rick’s cool weather layer-game is sadly unrepresented. While Rick Steves’ Boomer dork look is sensible for travel and appreciated by those Gen-Xers drawn to dad-nostalgia, it does not appeal to my particular sensibilities.
Shall we instead look to the coolest travel show host of all time? Anthony Bourdain’s devil-may-care style is easily attained (jeans, t-shirt or plain button down), but his look was carried entirely by his own innate coolness.
In an episode of "No Reservations," he politely apologized, “I feel terribly underdressed, as usual.” Tony did not care much about clothes. I, however, am not cool enough to not care.
Sidenote: When Anthony Bourdain was still with us I soooo wanted him and Rick Steves to co-host a travel show. What a delightful odd couple pairing that would have been!
I’ve found the ideal balance of ease and panache in the wardrobe of Richard Ayoade, British comedic actor and host of Travel Man (2015–19).
Throughout the show, he’s seen in a tailored suit and tie, yet he downplays formality with his use of color, pattern, texture.
His two most distinct suits are an often-worn royal blue corduroy, and a canary-yellow workwear-looking suit worn only once in the Brussels episode.
The rest of the show has him in various light-colored, soft-shouldered suits and blazers.
Shirts are floral, checked, and a succession of solid colors (but rarely plain white).
Cooler climates call for a houndstooth coat or bright-colored snow coat.
It’s Richard’s choice in accessories that most clearly convey a sense of comfort.
In sunny climates, he wears a straw Panama hat or fedora, which is sometimes quite crumpled and rumpled.
A bucket hat brings an on-holiday playfulness to whatever suit he’s wearing.
In wintery Norway or Russia, his head is topped in a big fur hat.
Richard often combines a jaunty silk scarf with a Breton shirt. Yes, “jaunty”.
Travel Man takes on a literal jaunt. A typical t-shirt would of course be disappointing, but if it has thin stripes, now it looks like you’ve just stepped off the yacht you so capably sailed yourself.
Meanwhile, the scarf says “I just drove to the beach on my Vespa with a latte in hand.” In winter the silk scarf is left at home and replaced with a knit scarf in a geometric pattern.
A while back, I enjoyed a short stay at the Whiteface Lodge in New York’s Adirondack Mountains.
Built in a grand rustic style, this Lake Placid resort is impressive—it was even a location for an episode of HBO’s Succession.
Curious to observe the travelwear of the other guests, I expected I was in the perfect setting for a display of classic ivy / preppy style.
However when I sat down to breakfast, I saw a towering granite fireplace, a beautiful mountain view… and a mass of t-shirts, cargo shorts, and flip flops.
Clearly these travelers need to watch more TV.
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Just by making simple fashion decisions, you can boost your self-esteem, make you more productive and improve your career opportunities. Every week, I help 1,000+ men make the most of their wardrobe with fashion tips to upgrade your life.
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