My travel fashion has certainly changed over the years. I’ve gone from flowy shorts to denim cutoffs and loose t-shirts to crop-tops. The one thing that hasn’t changed, however, is that I like feeling confident and stylish no matter where I am or what activities I’m getting up to.
These are the clothes and companies that I go back to again and again for stylish travel clothes for women who want to be active while still feeling cute. This list covers all seasons, weathers, and activities whether you want a beach packing list or you want to know what to wear for a weekend winter getaway.
Stylish Travel Clothes for Women
Always Consider the Culture of Each Country
One of the most important things to consider before you start shopping for travel clothes or packing your suitcase is what is appropriate to wear in different countries or even specific cities that you visit. For instance, if you’re traveling to more rural parts of Mexico or other parts of Latin America, you probably don’t want to wear short-shorts or mini-skirts. It’s simply not the done thing and you will garner unwanted attention for yourself. However, anything goes in beach towns like Cancun, Tulum, and Puerto Vallarta.
While it would be amazing if you could wear whatever you wanted whenever you wanted, that simply isn’t the case in the world. It’s so important to consider what is appropriate, and in some instances, what is legal and illegal to bring with you and wear. Look up what local women wear in the country you are visiting and always be culturally aware of the places you are visiting. Remember, you are a guest wherever you travel to and respecting the cultures of the places you visit is more important than looking good for your vacation photos.
Shopping While You Travel
One of my favorite ways to feel stylish while I travel (and once I return home, too) is to shop while I travel. I love finding little boutiques selling clothing that I would never find in the malls back home or markets with handmade shirts and skirts and bags and jewelry. I love spicing up an outfit with something unique and a lot of the pieces that I still travel with today have come from past travels in Bali, Australia, New Zealand, Thailand, and Vietnam.
I encourage you to browse around shops, buy locally, share the wealth with the places that you travel, and you’ll take home pieces that will make you feel even more stylish the next time you pack your bags and hit the road.
T-shirts are a must for any stylish gal’s travel wardrobe. Whether you’re traveling to a hot place or you’re planning a trip to somewhere wintery, t-shirts are a staple in my wardrobe year round.
My absolute favorite t-shirts are these V-neck shirts from J.Crew. Whenever I’m back in the US, I stock up on tons of them in all different colors and patterns.
Another t-shirt style that I’m really loving at the minute is crop-tops. I like buying this plain style or picking up bilowy crop tops from stores like Urban Outfitters. They look great with high-waisted shorts or skirts in the warmer weather or under a pair of overalls or with high-waisted jeans in warmer climates. They’re an easy way to style what would normally be a plain outfit.
No matter where you’re going, you’ll want to have at least a light sweater. If I’m going somewhere warm, I usually pack a thin cardigan like the Jackie cardigan from J.Crew (as you can see, I have a thing for J.Crew). It’s really light and folds up easily into my purse so I can carry it around during the day and then pop it on when it gets chilly.
If I’m packing for a colder climate, I’ll pack a few thinner sweaters that I can layer over t-shirts. I also love thick, wool sweaters like this one from L.L. Bean. Last year I got a very warm blouson sweater (similar to this one) from an outlet store in the Christmas sales and it has been my go-to for cold weather travel destinations. It looks cute under a blazer, fits under a coat easily, and I can layer a t-shirt under it for added warmth.
Trying to find the perfect jacket for travel is ridiculously hard. In the last ten years, I’ve been on the search for a jacket that I can easily fit into a carry-on, that will keep me warm in New York winters and dry in the UK. This year I finally found that jacket, the North Face Thermoball. It’s super lightweight but is still warm.
I’ve written a full post about why I think this is the only jacket you need when you travel which you can read here.
Finding cute winter boots is a challenge. For a long time I just wore brown leather boots with wool boot socks, but after spending a month in Copenhagen during the peak of winter, I quickly discovered that brown leather boots are not great winter shoes.
If you want a pair of boots that look stylish and keep your toes warm during a Scandinavian winter as well as a wet British winter, then I highly recommend getting a boot that is waterproof as well as lined with wool or faux fur. Another key factor to keeping those toes warm during the winter is to make sure that your boots aren’t too tight. If your toes don’t have enough wiggle room or they are slightly snug, you’ll actually feel colder sooner because you’re already limiting the blood flow to your tootsies.
A few of my favorites that aren’t too expensive are Dr. Martens fur-lined Serena boot, Tretorn Chelsea Rain Boots (these are my absolute favorites!), and Sperry duck boots which come in tons of cute colors.
If you’re traveling during any other season besides winter, leave those boots at home and travel light. I usually pack two pairs of shoes when I travel to warm climates, my J.Crew ballet flats or my Clarks Brogues and my Rainbow Sandals. Depending on the time of year or the place I’m visiting, I’ll usually bring a pair of flats in either black, navy, or grey so that they will definitely match with everything. I find the J.Crew flats to not only look good, but they keep my feet happy after a long day of walking, too.
My Rainbow sandals are the best walking shoes that I have ever owned. I literally never travel to a warm destination without them in my bag. I can walk in them for hours, they come in cute colors, and as long as you’ve got a pedicure, they’ll look relatively stylish. They also make a pair with a braided band for added style.
If you’re not much of a ballet flat wearer, then consider a stylish pair of sneakers like Adidas Stan Smith’s or Nike sneakers like this pair. While flat sneakers like converse look cute with everything, they will absolutely kill your feet and lower back after a day of walking.
Skirts are a nice alternative to jeans or other pants when you travel, especially if you go to warmer climates. I almost always pack a few skirts of varying lengths and styles and usually wear them with crop tops and t-shirts. Skirts are also a nice option for winter destinations and can actually be even warmer than jeans if you pair them with thick, patterned tights (my favorites are these from Nordstrom and I always stock up on them when I’m back in the US).
Skirts that I love to wear while I’m traveling are cotton pencil skirts, long patterned maxi-skirts, and mini-skirts made of firm materials like denim or cord, but with cute patterns like this floral skirt from resort perfectionist Lilly Pulitzer. I find that if I pack a mini or even a midi skirt that is made of a very lightweight fabric, I am constantly holding it down thanks to wind or fans or other strong breezes.
I’m a big lover of jeans. I pack them almost everywhere I go or I will wear a pair on my flight or bus ride. I almost always pack a pair of jeans unless I’m going somewhere really hot (like my upcoming trip to Cartagena definitely won’t include a pair of jeans). They’re great for places that get a little bit cooler at night or for winter destinations that aren’t freezing during the day.
As a petite woman with a more muscular build, I really struggle to find jeans that fit. The only place I have managed to consistently find great jeans is American Eagle. I may feel like a teenager when I go in there, but I love their jean selection and they always fit me perfectly. If I’m going somewhere warm, I’ll only pack a pair of thinner, light wash jeans. If I’m going somewhere that I know I’ll be wearing jeans most days, I’ll pack a second pair of dark wash jeans for evenings.
If you’re going somewhere really cold, jeans aren’t the best option. I sometimes layer a pair of long johns underneath my jeans, but still, the fabric stays quite cold and makes my thighs really chilly. For colder climates, I highly recommend cute snow pants like these from The North Face or other trousers made of fabrics other than cotton (wool and silk are great for cold weather).
Shorts are great for hot weather places and can easily be styled up to look cute enough for city strolling. I usually opt for a pair of denim cutoffs that I make myself from an old pair of jeans (or an old pair of my boyfriend’s jeans for a looser fit). These are great for hiking, beach going and casual exploring days.
If you want something more stylish to wear, I love patterned, high-waisted shorts like these seersucker shorts from Oasis or low rise patterned shorts like this pair from Vineyard Vines. Both look great paired with a crop top or with a tight tank top tucked in. Add bright lipstick and a statement necklace and you’re good to go for a day of cafe hopping and boutique wandering.
Travel dresses are a perfect way to feel stylish without actually having to put much effort into packing and styling your outfit on arrival. I love buying cute sundresses when I’m traveling to a beachy destination. They are always the most colorful and flowy. However, if I’m buying some travel dresses before I go on my trip, I usually look on Asos or Nordstrom for reasonably priced options that last a long time and easily transition from day to night.
A great tip for changing things up without spending a fortune or overpacking is to bring a few different belts with you. I usually pack two or three dresses for a trip and bring along several different belts that go with all of the dresses. That way you can re-wear some of the dresses but still feel like you’re styling it in a totally different way.
While a sarong isn’t technically clothing, I often wear mine as a dress or skirt when I’m headed to the beach. Sarongs should be on every stylish woman’s packing list. They are perfect as a beach blanket, as a hair wrap, as a skirt, a dress, a blanket on a chilly plane or bus, and a pillow when you’re at a budget hostel.
I picked up my sarong YEARS ago in Bali (2011 I think) and it is still going strong. It dries quickly in humid climates and is a perfect way to go from beach to beachside restaurant without having to put your t-shirt back on over your sticky, sunscreen-covered skin.
Hats are a must if you’re traveling to a hot place or to the beach. There’s no reason to wear your boyfriend’s baseball caps (unless that’s your style, then totally rock it). Opt for a cute Panama-style hat like this one or a large-brimmed beach hat like this one. Paired with a cute pair of sunglasses it not only looks stylish, but it’s sun smart. Gotta keep that skin looking young and fresh!
When it comes to finding the perfect travel bag, I have a few requirements: big enough to fit my camera, phone, and a sweater (and probably my boyfriend’s sweater), has a zipper so that it closes fully, has a comfortable strap, is preferably a cross-body bag. Back when I only used a small camera, I was obsessed with these Coach crossbody bags. They come in fun colors or you can get them in plain black or brown. If you get it in nylon, you can easily clean it, and it fits just enough for a day out.
After I bought my DSLR, I had to find something slightly larger. I have a few bags that I alternate between depending on where I’m traveling to or what I’m in the mood to wear. My parents went to Italy and brought me back a fantastic leather cross-body bag that has been one of my go-to travel bags. You can find a similar one here.
I also love this backpack from Hershel. It’s sturdy, easy to clean, stylish, and fits absolutely everything without being too oversized. They also make this gorgeous patterned one that I am adding to my wishlist!
Other Stylish Travel Essentials
I absolutely love wearing bright colored lipstick no matter where I am, but especially on a hot beach holiday. These matte glosses are great because they are long lasting and they dry on your lips so they don’t rub off when you smooch your partner (which makes them my boyfriend’s favorite, too). I also never travel without this SPF colored gloss from Fresh. It’s perfect for beach days when you want a light shine but also need to protect your lips from sunburn.
I also always travel with a few pieces of jewelry. Nothing too expensive or heavy, just one or two pairs of fun earrings for dinners out, a few rings and bracelets, and at least one necklace. Jewelry is my favorite thing to buy when I’m traveling and almost all of the jewelry that I own has come from local markets and shops that I find on my travels.
When I go somewhere cold, I always pack a really colorful scarf like you see in some of these pictures. It always makes me feel happy to put on a bright pink or orange scarf to pair with my muted jeans and jacket. It adds a pop of color and is a great thing to pick up on your travels that will last for years and years. Pretty much all of the scarves I own were bought on my travels.
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