My Top Ten Favorite Travel Looks

There are different kinds of travel. From the sunny Caribbean, to a snowy Montreal to adventurous underground caves and a night out in a city.These are some of the things I consider when packing for a trip. You have to be prepared. At the same time, you can always buy clothes from which ever city you are going to. Either way, traveling in comfort and style is important to me. Who likes looking awful in a vacation photo? I do love dressing up for travel. Usually, the trip or the destination itself influences how I dress up for the day.

Here are some of my favorite travel looks:

The Romantic Look


Romancing Athens at night was lovely. The old world backdrop definitely added that fairy-tale like atmosphere. Wandering around the historical sites and under the stars made it look like a scene from a movie. I wore a simple long silk dress with a splash of color to complement the night.

The Beach Look


This is the simplest look of all! For a beach destination, all you need is your sunglasses, beach hat and a great bikini. And a good book won’t hurt.

The Desert Safari Look


Going to Dubai in February is tricky. It is warm during the day and cool at night, although some nights are cooler than others that you would need a light jacket. When I went on a desert safari, it was a bit windy but the weather was perfect. I loved this outfit! I’ve always wanted to wear harem pants so I got myself a pair in Dubai and paired it with a light jacket, white top and an animal print silk scarf.

The Adventurous Look


This was one of the most extreme adventures I’ve been on. Wild caving expedition  in West Virginia was fun, challenging, scary and exhilarating all in one! In any extreme adventure, I always check if the tour or excursion I am going to has any required clothing. Usually, they do. I expected to get down and dirty so I knew I have to wear clothes that I am not afraid of damaging. From hiking boots and backpack, to comfy jeans and water-resistant  breathable undershirts, I came prepared!

The City Girl Look

new yorker

The City Girl look involves a lot of black and texture. I like mixing up my lace and leather all the time. Wandering the city also means wearing walkable shoes. I was in New York City when this photo was taken in the fall and you can never be overdressed in NYC!

The Island Girl Look


My favorite look has got to be the Island Girl look.  It’s pretty simple: bikini and a beach dress. Done.

The Explorer Look


When your itinerary is composed of historical sites and ruins in the middle of summer, it’s best to wear your most comfortable clothes. This definitely does not mean to forego looking stylish. Meet in the middle. I usually go for light colored sleeveless tops when I know I will be under the sun. Don’t forget a hat for those strong sun rays.

The Party Girl Look

party girl

Painting the town red is hard work. Getting ready for this is harder! When traveling, I bring clothes that I can mix and match. Thankfully, these outfits tend to be lightweight and flimsy anyway so it doesn’t really take up room in the luggage. Ha! I also take my comfy dancing shoes with me. Those sexy heels that I’ve already used many times for dancing and won’t kill my feet.

The Garden Party Look

plantation look

The Garden Party look is when I have wine tastings to go to or plantation tours or anything that involves outdoor parties and adventures in a country setting. I usually go for a subtle floral dress or skirt and comfy wedge heels for those uneven landscapes.

The Snow Queen Look


As much as I love my skirts, I have no choice but to bundle up for winter trips and snow adventures. I do like accessorizing with a scar, hat or ear muffs and layering allows me to play with texture and colors!

Most of all, I think it’s important to be yourself and not try too hard. Style is a personal expression. Be true to your own sense of style!

What’s your favorite travel look? If you enjoyed this post, let me know your thoughts by commenting below. You can also connect with me onFacebook, Twitter and Instagram.


Jen is a Chicago-based traveler and a full-time Director of Development for an arts & culture organization. Originally from Connecticut, she created JetsettingJen as a place to share her travel stories and photos with friends and family. Now, it is a place for adventurers, explorers and dreamers. Its purpose is to inspire and encourage people to see the world and achieve a better work-life balance.