How to Dress Stylish While Traveling

How to Dress Stylish While Traveling

It is possible to look stylish while traveling with a little more planning. You don’t have to sacrifice style for practicality!

Packing clothes for a trip can be an incredible hassle. With many airlines charging growing fees for checked baggage, packing light has become not just an issue of space but of economics, too.

In my twenties, the only thing I cared about was how much my bag weighed. Now, in my thirties, I carefully consider what goes into my suitcase — so I can save luggage space and still remain stylish.

Staying Stylish While Traveling

How to Look Stylish While Traveling


Travel Clothes for Women: Pack Mostly Basics

About 70% of the clothes you pack should be basics, not statement pieces. Dark blue jeans, a black skirt, a cute sundress, shorts or a warm coat, depending on the local climate, and a few dressy-casual blouses can all be mixed and matched to fit any occasion.

By stocking the majority of your suitcase with basics, you remove the need to pack a different set of clothes for each activity.

La Jolla San Diego Sunset

For example, wearing a plain black or white tank top with some dark jeans or shorts can be perfect for physical activities like hiking, biking, or just exploring a city by foot. That same tank top, when tucked into a black skirt and covered with a cardigan and a scarf, becomes a cute and flirty outfit for a dinner in town.



While most of my clothes are solid colors while traveling, I do have one or two colorful dresses and pairs of shoes to brighten up my outfits. For instance, this dress goes with me almost everywhere.

From the vineyards of Emilia Romagna to the beaches in Mexico, this cotton dress pairs perfectly with a cardigan (I love this cardigan or long-sleeved solid top — and it doesn’t wrinkle in my suitcase.

How to Stay Stylish While Traveling



Another way to spice up an outfit is by packing a colorful pair of shoes to go with solid colors. These are my favorite travel shoes and I get compliments every single time I wear them — even from men!

They go with jeans, shorts, dresses — basically any  solid-colored outfit — and they have an extremely cushioned insole with amazing arch support. I found them at a surf shop in San Diego, but they sell them cheaper on Amazon!

Boots are another great item to liven up an outfit. Not all boots pack well, but I found a cute pair of knee-high boots that don’t take up too much space in my luggage. I normally end up wearing them on the plane, anyway, because they are so comfortable.

These ankle boots are a good option if it’s too hot for knee-high boots.



I’m slightly addicted to buying cute scarves and have a drawer full of them at home. It can be tough to pick just one scarf to bring on a trip, so if I’m traveling somewhere cold, I might sneak two or three into my bag.


Work with Layers

Layering is the key to dressing your outfits up or down. A little black dress for that night on the town, for example, becomes a lot more appropriate for day wear when it’s topped with a shrug or sweater and worn over dark stockings.

Similarly, dark jeans with a plain blouse can quickly become dressed up with a well-fitted colorful jacket or long scarf used as a shawl.


Dress Up Your Travel Outfits with Accessories

Like with your clothing, keeping your accessories fairly simple means they will fit more easily with any outfit. Small gold or silver studs, a nice pendant, and your favorite charm bracelet or watch should cover most of your needs, whether you’re going dressy or casual. You would be surprised how easy it is to do a lot with just a few accessories!

I have a few cuff bracelets that always stay packed in my toiletries bag — so I never forget them when packing for a trip. Turquoise and silver bracelets go great with solid-colored clothing.


If you need something flashier or realize you have forgotten something at home, there’s always the opportunity to shop for souvenirs at your destination. Whether it’s a necklace, sunglasses, or a new scarf, chances are that the place you’re going has its own unique style.

Purchasing your accessories at your destination can be a fun way of incorporating that local style into your wardrobe, as well as getting a nice memento to bring home with you.


Consider Your Destination

Obviously if you’re going to Yakutsk, Russia, you don’t want to pack shorts and a swimsuit. Similarly, a trip to Mauritius is not the place for heavy winter coats and turtlenecks. I always joke that it’s easy for me to pack for a tropical destination — I just throw in a few sundresses and five bikinis.

How to Stay Stylish While TravelingBikini bottoms by Luli Fama


It’s much more difficult to pack light for a cold weather destination, so this is where layering really comes in handy. Don’t forget scarves, gloves, a beanie, and warm socks. This slouchy knit oversized beanie keeps me warm and — depending on what color you choose — it can brighten up an outfit.

Considering your destination while packing involves more than just packing for the geographical climate — it also means being aware of the cultural and political climate of your destination, too.

If you’re visiting Istanbul or another location whose culture sports a more conservative style, be respectful and wear longer shirts, skirts, or pants. While it will matter less in more cosmopolitan areas, in rural areas your different style of dress might be considered rude or inappropriate. Research your location before you pack to get an idea of what other travelers have found works best.

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  1. Thanks, Christy! We’re going for a one months trip to Eastern Europe with Travel all Russia, so I need all the information on what to pack! As you mentioned- we’re going to Russia, so the weather is unpredictable, there are warm places, but it can get very cold as we will travel Northern..

    1. Ordinary Traveler says:

      I’m so glad the post was helpful. Your trip sounds amazing!

  2. Emiko Atherton says:

    Thank you for this posts!! I’m traveling around the world and originally packed a more backpackers wardrobe. Well, I quickly learned what worked for me in my 20s doesn’t work for 30 something me. I’ve replaced most of my clothes with more stylish things (black pants, always black pants!), but I haven’t added jewelry. Great suggestions!

    1. Ordinary Traveler says:

      I’m so glad you liked it! I hear ya on the backpacker’s wardrobe. I cringe at my travel photos from my twenties.

  3. Hayley Swinson says:

    Great article! I always find myself bringing a couple of flashy scarves as my “pop” element. They usually pack light anyway, so I don’t feel bad bringing more than one. 🙂

    1. Ordinary Traveler says:

      Thanks! Are you a scarf collector too? 🙂

      1. Hayley Swinson says:

        It’s hard not to be! Although lately I’ve been trying to give a lot of them away and only keep my favorites 🙂

  4. Loved this! I might just buy those shoes too… they’re super cute and would go with so much I think!

    1. Ordinary Traveler says:

      You won’t be disappointed. I’m so glad you enjoyed the post!