Tips for Dressing Stylishly While Traveling

February 03, 2019 8 min read

When preparing for a trip, we tend to focus our energies on booking hotels, researching attractions, planning routes and learning about the local culture. Planning our outfits, unfortunately, is often one the last things on our minds.

Just because we're away from home, however, doesn't mean fashion should be neglected. After all, dressing a little stylishly can heighten the experience by adding some of the old charm back into traveling. You also don't know who you might meet in a foreign place — it could be a new friend, and potential business partner or maybe even a romantic interest. If you dress well, you'll be prepared to meet anyone.

Furthermore, in many places in the world, you're probably going to stand out. So if the locals are going to be staring at you anyway, you might as well look your best.

Looking stylish, of course, doesn't necessarily mean walking around in a suit and tie. You just need to pack a few items that are both attractive and comfortable. This guide will provide some tips on how to look your best and feel good when you're living out of a suitcase.


Finding Stylish Travel Clothing


When searching your wardrobe or shopping for stylish travel clothing, keep the following four things in mind:

  • High-quality: This refers to how well the clothes are made and how resistant they are to tearing and abrasion. The seams should either be double sewn or contain at least 12 stitches per inch, and even more for pressure points and tight fabrics such as shirts. Cotton and wools are great options for travel, and if you're going to a location with extreme weather, consider looking into synthetic fabrics and specialty travel clothes.
  • Comfortable: Vacations are times when you're supposed to enjoy yourself, but if your shoes are too tight or your pants are chafing, it'll be harder to have fun. Ideally, the clothes you bring on a trip should be worn many times beforehand. Comfort is especially important for shoes.
  • Classic: Choose more conservative, less gaudy clothing if possible. Your outfits should also go with your complexion and build.
  • Single-color: Picking one color just makes things so much easier when trying to match items. The easiest colors to wear and mix are blacks, whites and blues. They also work in a wide variety of climates and locations.

Luckily, finding travel clothing is easier than ever before. Men's travel wear is becoming more comfortable, affordable and stylish, and shirts and pants with wrinkle-free and sweat-wicking fabrics are becoming the norm.

Tips For Traveling In Style

Here are our top recommendations for stylish travel clothing items and some of their practical benefits:

1. Hats

The hat is a classic accessory for men that has decreased in popularity over the last 50 years. This is unfortunate, as hats can be stylish and come with some practical benefits.

First of all, they're functional — they protect you from harsh elements such as rain, snow and sun, make you appear taller than you are and mask baldness or any imperfections on the top of your head. Wearing a hat will make you look and feel better.

Secondly, they're timelessly fashionable. For millennia, hats have largely helped to define the identities of the famous figures who wore them. It's tough to image cowboys without cowboy hats, Russians without their ushanka or Frank Sinatra without his fedora.

A few of our hat recommendations include:

  • Panama hats: The Panama hat is a lightweight, lightly-colored straw hat with excellent ventilation, making it perfect for tropical, seaside destinations. Also, this style was a favorite of Humphrey Bogart, and who could question his fashion sense?
  • Crushable hats: These hats are made for travel and can handle a fair amount of compacting in your suitcase. Crushable hats are durable and will look as good as new with a little steam.
2. Shirts

If you have the room in your suitcase, it's best to bring along a few different types of shirts, including:

  • Button-down: Even if you're traveling for leisure, you never know when you might have to dress up. Packing along a simple button-down is an excellent idea because it can easily go with a blazer and denim if you want to go to a fancy restaurant or concert. Without a blazer, it is still an excellent semi-formal look.
  • Coat or Jacket: If you're traveling to a place with cold or wet weather, you might end up wearing your coat more than any other item in your suitcase. Some stylish options include trenchcoats, wool overcoats and weatherproof microsuede jackets. Whatever you choose, make sure that it fits well and doesn't have ostentatious colors or patterns.
  • Suit: If you're traveling for business, you'll likely need a suit at some point. It's a good idea to wear this while traveling, as it will avoid getting wrinkled in your luggage.
  • Sweaters: If you're heading to a place with cooler weather, there are few items more ideal than sweaters. They're fashionable, functional and, with the right cut and color, can go well with many combinations of clothing. If you have a light cashmere sweater, for instance, you can use it to dress up jeans and a shirt or dress down a two-piece suit. They're also easy to maintain, as they are durable and don't have to be ironed. Bulky sweaters may take up a lot of space in your suitcase, so you might want to wear one while you're traveling.
  • Undershirts: Undershirts are helpful because they help keep your shirts and jackets clean. Not only do undershirts keep you looking fresh for longer, but you can easily wash and dry them in the evening.
3. Accessories

Most men these days don't accessorize much, but it's one of the easiest ways to be fashionable on vacation. This is because accessories don't take up much space in your suitcase but can completely transform your look.

Our most important tip regarding accessories is to keep them to a minimum. If they don't serve any purpose, don't bring them along.

  • Belts: Belts are a must-have accessory. The right belt can complete an outfit and bring some polish to an otherwise casual look. Belts don't take up a lot of space in your luggage, but if you're short on space, consider a reversible or two-tone belt.
  • Sunglasses: Whether you're on an airplane or a tropical beach, sunglasses will make travel more comfortable. Large, darker-tinted glasses are especially effective at protecting you from window glare and helping you sleep — just make sure that the pair you choose suits your facial features. Sunglasses are one of the items that travelers are most likely to forget to bring, so make a note to pack them.
  • Scarves: If you're bound for a colder destination, a scarf is an excellent accessory. It keeps your neck warm and goes well with winter jackets, tee-shirts or button-downs.
  • Suspenders: If you want to take your personal style one step further, wearing a tie and suspenders is a great idea — just remember to bring a tie clip, too.
4. Undergarments

Unless you're planning to without pants, your underwear is probably not going to affect your look. So in this section, we're going to focus merely on undergarments that maximize your comfort and convenience while traveling. Here are three criteria your underwear should meet:


Your underwear should be comfortable to wear and versatile. We tend to partake in a wide variety of activities when we travel, including walking, running, climbing and exercising, so your underwear should be suitable for all of these things. To achieve this, your undergarments should be made of a light, soft and breathable fabric. An elastic waistband that wicks moisture is also a plus.

Cotton boxer-briefs should be avoided, as they will stretch out easily and lose their shape, making it easier for them to ride up on your legs. Also, if cotton gets wet, it will likely cause chaffing.


When you're traveling, especially if you're only taking a carry on, your space is limited. To make the most of it, make sure to buy underwear that will pack down small.


Your underwear should be made of a material that dries quickly. Regular cotton underwear takes a long time to dry, and when it does dry, it's often hard and rough, which won't be much fun to wear. Cotton also isn't particularly effective at managing odors.

5. Pants

When it comes to pants, you have many options, including jogging bottoms for maximum comfort, chinos for a smarter comfort or jeans for a more relaxed and stylish look. Many people have been led to believe that jeans are uncomfortable when traveling, but this is not necessarily true. Just make sure you choose jeans with a slim or relaxed fit.

One particularly versatile item is a pair of dark-colored jeans, whether black, indigo or navy. Dark jeans can be either casual or formal, and you can wear them with practically anything and for almost any event. With a button-down and blazer, you can go out to a fancy dinner, and with a t-shirt and jacket, you can wear them for everyday use. Jeans are definitely a men's must-have travel item.

It's also worth it to include a more formal pair of pants in a fabric that is suitable for the season. Wool is an excellent choice for winter, and cotton or linen works well for the summertime.

6. Shoes

Picking the wrong shoes can be a serious mistake. Before choosing a pair to accompany you on your adventures, you need to consider the following:

  • They should have support and insoles. Your shoes should have proper foot support. High-quality insoles will make shoes and boots feel much more comfortable.
  • They should be destination-appropriate. This one may be obvious, but your shoes should be suitable for the location. Sandals are probably not the best choice for the mountains of Iceland, and heavy-duty hiking boots are probably overkill for the streets of Paris.
  • They should be broken in. Make sure the shoes you want to bring are broken in. If you're going to buy new shoes, do so a month or two before your travels so you can wear them frequently before you leave.
  • They should be breathable. Feet tend to swell when on an airplane, so make sure your shoes will let your feet breathe.

Because we're aiming for fashion as well as comfort, ensure that your shoes go with the rest of your outfit. At least one pair should be able to pass for both casual and dress shoes, and you should be able to use them almost every day. Black and brown tend to be the easiest colors, but for some people, blue or red sneakers work just as well.

Shoes are often thought to be the most important part of one's look, so you should put extra time into picking a pair that's stylish and versatile. This also means you should make an effort to clean them regularly during your trip.

Here are some recommendations for stylish and comfy footwear for your travels:

  • Boots: Boots are a great choice for men who travel because they protect your ankles when the weather's bad, provide support and, if they contain the right sole, are great for walking. If not too casual, you can also wear them with a suit or sports jacket.
  • Loafers: If you don't feel like untying and retying laces when going through security — or only have space for one pair of shoes in your suitcase — then loafers may be the best option for you. You can easily slip them on or off and they're quite versatile, looking equally as good with a suit as with a pair of jeans.

Update Your Travel Wardrobe at Penner's

Travelling is always more enjoyable when you look and feel your best. At Penner's, we have a broad selection of items, including shirts, suits, pants, hats, shoes and accessories to enhance your next travel experience.

If you live in or around San Antonio, Texas, you can also drop by our store. Our friendly and professional staff includes seven full-time, in-house tailors, many of whom have over 25 years of experience. They are passionate about making you look as good as possible in your outfit — and all alterations are free of charge at the time of purchase.

Penner's is a family-owned business that has been providing San Antonio with the highest-quality men's clothing items for over 100 years. In addition to premium products, we also provide superior customer service. Call us at (210) 226-2487 or write to us using our contact form, and we will answer all of your questions as promptly as possible.

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