Best Travel Outfits for Every Occasion

Best Travel Outfits for Every Occasion

If you’re going to rotate the same few outfits in all your travel photos, they’d better look pretty good, right? Well, our team at SiteSee sure thinks so — which is why we’ve set out on a never-ending quest to find the best travel clothes for every occasion!

6 best travel outfits

Even though you’re far from home, you still want to feel like yourself when you’re out on the road and exploring new places. The ideal travel outfits stay within your personal style range, but they also follow a similar color scheme so they’ll complement everything else in your bag. 

These six recommendations do exactly that, giving you functional, versatile pieces that’ll really expand your outfit possibilities and keep you from being weighed down by your wardrobe.

1. Airport outfit

When you’re headed to the airport, there’s no doubt you’ll want to be comfortable — but who says you can’t look chic at the same time? Not only is this outfit totally stylish, but it’ll provide comfort on a long-haul flight (or any flight, for that matter). What’s more, the slip-on shoes will help you cruise through security so you have time left to grab coffee before boarding.

Outfit details: 

  • Black leather jacket
  • Mock neck T-shirt
  • Cute joggers
  • Slip-on sneakers
  • Easy-carry bag

*Although it’s not pictured, we’d also be in support of a baseball cap here!

2. Road trip outfit

Whether you’re road tripping solo, with your best pals, or alongside your S.O., it’s best to wear something relaxed while you’re on the road. Opt for pieces that are breathable and easy to layer in case temperatures fluctuate throughout the day. This look is practical enough for long hours in the car, but pulled-together enough to snap in a photo when you stop at roadside attractions.

Outfit details:

  • Denim jacket
  • Breezy muscle tee
  • Athleisure pants
  • Comfortable trainers
  • Accessories of your choice

*Don’t forget your favorite sunglasses and your reusable water bottle, too!

3. All-weather outfit

If you’re headed for a wet climate, or you just want to be prepared for all kinds of conditions, you should definitely bring items that are weather-ready. Go for a crewneck sweatshirt and some sporty leggings, and pair them with a rain jacket that has plenty of pockets. Then, be sure to pack shoes that are water-resistant, so you won’t have to tour the town with soggy feet.  

Outfit details:

  • High-waisted leggings
  • Cozy sweatshirt
  • Flattering rain jacket
  • Water-resistant footwear

*If you don't have room in your bag for a full-length jacket, a cropped style will still do the trick. 

4. Sightseeing outfit

To create the perfect sightseeing outfit, prioritize stretch to help you avoid feeling uncomfortable halfway through the day. A casual top and bottom (like those pictured) also offer amazing versatility, which means they can be mixed and matched with the other garments in your suitcase. Complete the *fit* with a roomy tote to hold all the fun souvenirs you find!

Outfit details:

  • Striped top
  • Casual pants
  • Bright sandals
  • Woven bag
  • Flirty hoops

*A durable canvas tote would work well in lieu of a woven design, as well.

5. Daytime outfit

A daytime outfit is great for spending the morning at a cafe, or touring a museum in the afternoon. To achieve this look, be sure to include a soft tee, loose-fitting pants, and some supportive walking shoes that can keep up with all your exploring. We tend to lean toward a lighter palette during the day, but you can wear whatever colors or patterns feel good to you.

Outfit details:

  • Crew or V-neck tee
  • Straight leg pants
  • Lace-up sneakers
  • Tortoise sunglasses

*You can also accessorize with a neckerchief to amp up the cute factor on this one.

6. Date night outfit

Wherever you’re off to, you're smart to pack at least one outfit for date night. That’s because when you treat yourself to a nice dinner, or go out with your girlfriends, or head somewhere romantic with your partner, you’ll want to look as good as you feel. This ensemble is equal parts sweet and sassy, and even lets you reimagine the leather jacket you wore to the airport. 

Outfit details:

  • Black leather jacket
  • <Printed camisole
  • Slim-fitting jeans
  • Dressy footwear
  • Accessories of your choice

*If you need options that can transition from day to night, you can’t go wrong with a jumpsuit!

Wrapping Up

When it comes to travel outfits, our best advice is to stick to the basics. That means packing neutral-colored clothes you can easily interchange, and looking for fabrics that are lightweight, compact, and flexible. This way, you’ll minimize the amount of clothing you bring and maximize the amount you can do in a day, since you’ll stay comfortable for hours on end.

Travel Outfit FAQs

What should you not wear to the airport?

As you’re headed for the airport, there’s a few articles of clothing not to wear so you can have a smooth trip through security (and the most enjoyable flight possible). For example, you’re wise to forego flip flops or heels, leave your jewelry in its case, and stash your skinny jeans for another day. Instead, opt for slip-on sneakers or trainers, wait to put on jewelry until you’ve reached your destination, and wear joggers or loose-fitting pants for the ultimate relaxed vibe.

How can you look stylish while traveling?

To look stylish while traveling, pack versatile pieces you can layer or mix and match to make multiple outfits. Key pieces in a trendy travel wardrobe include a cropped leather jacket, V-neck or muscle tee, high-waisted leggings, straight leg pants, sporty trainers, and fun accessories to polish off your look (sunglasses, baseball cap, neckerchief, reusable tote, etc).

What are the best clothes to wear traveling?

The best clothes to wear while traveling are compact and lightweight, so they can be rolled or folded into packing cubes for quick, convenient storage. In addition, the optimal travel wear is also wrinkle-resistant, moisture-wicking, and quick-drying, properties which help you stay fresh and looking sharp no matter where the day (or your adventures) may take you.

Meredith is a freelance copywriter based in Des Moines, Iowa, not far from where she grew up. She earned a degree in journalism from Belmont University, and has been writing remotely for a variety of brands and businesses over the last seven years. To read more of Meredith's work, check out her portfolio here.


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