How to Dress Comfortably and Stylishly When Traveling
Look and Feel Good With These Travel Style Tricks
It can be an interesting and sometimes frustrating experience when you’re trying to look good but also remain comfortable while traveling. As someone who travels full-time, my single checked bag and backpack must carry all my worldly possessions. The question is always, how can I look good without needing ten suitcases?
We don’t often think about style while traveling, but we should. Dressing to impress can put you in the best position to get upgrades, better treatment from flight attendants, lounge staff, and other travel professionals, and may even catch the eye of someone you fancy.
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You’re probably not going to wear a suit while traveling, as that’s simply not comfortable. You also have space and financial considerations when planning what you’ll wear while traveling. There has to be a balance between comfort and style.
“A man has to be comfortable yet elegant,” says Minesh, an entrepreneur who frequently travels while looking stylish. “As someone who travels full-time, my suitcase is packed with Public Rec trousers or sweatpants, a soft tee, my Berluti Shadow sneakers, and the accessory that completes my look are noise-canceling headphones. No matter how long the flight is or what happens, these interchangeable clothing options are just what I need.”
Here’s how to dress comfortably while traveling with some advice from stylish frequent travelers.
Pack Outfits That Can Be Used Interchangeably
One trick you can use is picking clothing that can be used interchangeably. Have shirts, shorts, pants, and jackets that are of a neutral color and can be used in combination with the others.
Having interchangeable outfits gives you the best look without filling five suitcases with single-use outfit choices. Think through clothing choices that are not too casual but not too dressy. The goal is outfits that are appropriate for any situation.
“The key to keeping stylish while traveling is understanding the core difference between wants and needs,” says Alan Howard, a men’s transformation coach and full-time traveler.
“Bring the variety of clothes you need to fit the ever-changing environments. While traveling with a carry-on for two years, I realized the key is having core items. Pack two pairs of jeans, one nice jacket that can be used for colder weather and upscale places, and two high-quality Henley style button-up shirts — they can be dressed down and dressed up, worn with shorts, or worn in upscale clubs. The black jeans are the foundation as they can be worn casually or in upscale environments giving you utility without sacrificing style.”
Pack Based on What Activities You’ll Participate In
It’s easier to overpack than under-pack while traveling. The reality is that most of us don’t think through what we’ll be doing and what outfits may be needed for those activities.
The key to dressing well while traveling lies in your planning. Look at your schedule ahead of time and plan outfits based on activities. You will ensure you have the outfit combos needed without overpacking.
“My travel essentials are dress shirts from SuitSupply or non-logo T-shirts from True Classic Tees,” says Marshall Terrin, an entrepreneur who travels often.
“The Traveler Collection from SuitSupply does not need to be dry cleaned and includes nice fitting blue jeans and a designer belt. Accessories go a long way. My favorite is my Rolex, but it can be a bracelet that compliments your personality and color choice. Regarding shoes, it’s always brown dress shoes for me.”
Pack Based on What Makes You Feel Comfortable
When it comes down to it, you have to be comfortable. You want to look good, but feeling good is also essential. What’s the point of dressing to impress if you don’t feel comfortable? That discomfort will show up in your energy.
When planning outfit choices, think about comfort first and foremost. You are the one who decides what works best for you. There has to be a balance between not giving in to limiting beliefs and stepping into your power as a man.
“I dress in extreme comfort when I’m traveling,” says Aaron Jetsetter Sutherland, an entrepreneur who owns a luxury travel company.
“My typical go-to would be a classic, ultra soft, premium Jetsetter-branded tee, paired with a lightweight jogger (flexible enough for laying flat on long haul routes) and a pair of Louis Jr. spike Christian Louboutin sneakers. I protect my eyes typically with my Givenchy specs.”
