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What to Wear When You Travel – From the Plane to the Hotel and Everything in Between

Ever find yourself flipping through a magazine or on Pinterest thinking, “I need a better travel style.”? We’ve all been there. And by there I mean in our sweat pants, at airport security, shamefully eyeballing the flawless woman ahead of you from head to stiletto. I realized some time ago that I needed to care about my travel look. This style guide will help you find exactly what to wear when traveling so you can feel good about your style. 


Whether you’re riding by bus, plane or train and arriving at a log cabin or a five-star luxury hotel, this will help you learn what it takes to travel in modern-day fashion.


What to Wear When Traveling 


Think About Your Wardrobe First


The first thing that comes to mind when the word style comes up is typically one’s fashion sense. There are many facets to cultivating a stylish look. While fashion tends to change like the weather, there are certain staples that represent a timeless class. 


what to wear when traveling


The primary thought to keep in mind when traveling is comfortability. You want to be just as sharp as you are comfortable to represent the sense of refinement. A ten-button shirt that is neither too snug or too loose is the first element to incorporate. Comfortably fitting khaki’s, jeans, or slacks are essential to convey your sense of sophistication.


Finishing touches may include a sports jacket, sunglasses, a hat, and slip-on loafers. These accessories come in handy when traveling due to uncertain weather conditions. Staying warm, cool, or dry will be factors that you may face while on your vacation.


How Are You Traveling? Travel Transportation and Your Fashion Choices


Flights, Charter Jets, First Class or Coach


How you arrive to and depart from your destination is a major part of the travel experience. Doing this with as much flair as possible is the key to earning style points. For those used to flying coach, first-class is always a step up. You want to consider these things when deciding what to wear when traveling.


jet, plane


On the other hand, for those that are looking for the ultimate flight experience, chartering a private jet is the only way to go. Flying via private jet offers luxuries and amenities that are unattainable when traveling on commercial flights. When traveling with a group, charter jet cost is often comparable and sometimes better than commercial fares. It’s definitely worth looking into.


Ground Transportation


Once you have arrived at your destination, it may be necessary to secure some transportation to maneuver around. This is yet another opportunity to take your style to the next plateau. 


If you prefer to be driven, limousine services are still the way to go. Rather than hire a stretch limousine driver, SUVs and luxury sedans are preferable forms of classy ground transportation these days. For those looking to drive themselves, renting a luxury sedan or exotic sports car is the way to go. 


Luxury Accommodations


Luxurious lodging is the hallmark of a stylish and classy vacation. If you have never stayed in a 5-star hotel or resort, you likely are unable to appreciate the added amenities and ambiance the added cost affords you.


what to wear when traveling


The attention to detail and service is a massive benefit that luxury accommodations offer. The size of your room and furnishings that adorn it will dwarf that of regular hotels. The check-in and check-out experiences are free from hassle and will to satisfy guests are other ways luxury hotels stand out.


Enjoy Exquisite Cuisine


Fine dining is another crucial part of high-class travel. Your dining experience must be one that is both exceptional and memorable. The objective is to locate the dining locations that are best known for their marvelous cuisine, as well as, glamorous atmosphere. 


dining, cuisine


If you are dining with a companion, this is where you really have an opportunity to solidify and further enhance the trip. A unique and elegant dining experience is one that will bring about good memories for years to come.


In Closing


This blueprint for stylish travel is just an outline of what a trip filled with sophistication and luxe is all about. The intention is to inspire your creativity by giving you tried and true ways to travel with extraordinary class.


Some of these suggestions may require budgeting and saving months ahead of your trip, but the results will speak for themselves. Trip expenses should never be looked at as spending, but rather as an investment in an unforgettable experience. 


Don’t short yourself or your looks. Plan out what to wear when traveling on your next adventure so you can feel confident and ready to take on your adventure. Not to mention, your photos are going to be on point! And who doesn’t want to look back and say to themselves, “I looked great in that photo.” 


Christa Thompson

Christa Thompson is the Founder and Chief Editor of The Fairytale Traveler. She started traveling the world in 2003 when she attended a summer abroad study at the University of Cambridge in England. Since then, her wanderlust has been fierce. Her three passions in life are her son, traveling, and being creative. The Fairytale Traveler brand gives Christa the opportunity to do all of these things and to live intentionally every day. "It's never too late to believe in what you love and to pursue your dreams." -Christa Thompson

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