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How to look stylish while traveling, ways to stay looking good while traveling

I strive to always look my best, no matter what I’m doing— and travel is certainly no different. It’s not the easiest thing to do though— we can’t all look like Jessica Alba does when we step off a 12-hour flight (I mean really, it’s just ridiculous how good she looks) but it’s no reason to be schlepping around an airport in a sweatshirt with greasy hair to top it off. Here are my top tips on how to look stylish while traveling.

Wear a hat

I’ve become such a hat person because they can really change a plain-jane outfit into something worthy of a fashion blog photo opp. On top of that, they can help you keep cool in the warm weather, protect your skin from the sun and can cover up your less-than-clean hair. I usually get my hats from Asos, but TopShop and H&M have some high-quality ones at decent prices as well. I don’t usually spend too much on my hats as I sadly left a beauty of a hat on a plane once…

Plan your outfits while you’re packing

Some may call this obsessive, but I call it a time-saver and the cure to my over-packing addiction…

When I’m packing for a holiday, I plan out each and every outfit that I’ll wear. This starts with writing up a rough itinerary of what we’ll be doing, including any nice dinners, day tours, etc. I then make a note of what type of outfit and footwear I’ll need for each part of the itinerary— for example, “casual day outfit with converse”, “nice dress with heels”, etc.

Finally, with the type of outfit in mind, I create each and every outfit on the floor of my room and document it by taking a photo on my phone. I know, I know… it takes some extra time and effort, but it helps me to be a much more efficient packer and I’m never stuck with a bunch of mis-matched options at the end of a trip. Try it!


what to wear to be stylish while traveling, how to look stylish while traveling

Watch out for what’s on your feet

Yes, they’re great for long periods of walking, but please stay away from wearing workout trainers on your holiday (unless, that is, you’re actually working out.) I’m sad to say that Americans are the most guilty of this—that comfort often triumphs over fashion but ironically this makes you stand out in the crowd, and tells everyone you’re a big ole tourist (and therefore you’re a prime target for pickpockets.) Stay comfy and still look good with some fashion-forward comfy shoe options, like Converse (my go-to), Stan Smiths, Keds, Sperrys, or Cole Haan’s Air Bacara Ballet Flats.

Master the art of slow travel

Blisters, sweat, and achy legs ain’t pretty. When I learned to appreciate slow travel, I found it much easier to dress stylishly while traveling. I was able to ditch the shorts-tank-sneakers uniform that I developed during my backpacking days and instead incorporated heels, dresses, and an appropriate shower routine (I know, ew.) Experiencing a destination slowly means no long days of walking, no missed opportunities to freshen up back at the hotel before heading out to a romantic dinner, and of course, getting the chance to know your location in a different way.

Rock a bold lip

I mentioned in my Must-Have Beauty Items for Travel video that I always bring bold lipsticks with me when I’m traveling. They’re so on trend right now and thank god for it because a bold lip makes me feel so put together and glamourous. And if you go for a bright pink or coral after a day at the beach, your new tan will pop! Watch the video for some of my favorites.


how to look stylish at the airport, how to look stylish while traveling, how to look good while traveling
Be stylish AND comfy

It’s completely understandable to want to be comfortable on long travel days, but there are plenty of ways to be comfortable without sacrificing your appearance. My go-to plane outfit is the classic combo of thick black leggings, a long, loose top and a scarf. The scarf pulls the whole outfit together, can infuse some color or pattern into it, and will help keep you warm. When the weather is hot, I go for a maxi dress or skirt instead, but still stick with the scarf. A maxi will keep your legs a bit warmer on chilly planes and trains, and the scarf can come off when you get start to get clammy.

Tailor your beauty routine

Depending on your trip’s duration, purpose, destination and such, your beauty regime for it will need to be different. Plan for the weather, the activities that you’re doing, etc. and bring the beauty products that will help keep the elements at bay. For example, when I’ve got a long day of travel ahead that includes a moisture-sucking flight, I rely on my Rimmel Stay Matte primer and powder to help me be a little less greasy-faced. For sunny holidays, I choose the products in my arsenal that include a decent level SPF so I don’t go tomato-red on day one. The same goes for hair products— think about what you’ll be encountering and bring along whatever it is that will keep your hair looking fresh and you feeling beautiful.

Don’t appear to be a cheapo (even if you are)

I have a fascination with people who radiate posh-ness without spending ridiculous amounts of money on clothes, eating out, etc., and it’s something that I strive for. Even if you’re short on cash, don’t let it show. Nothing’s less stylish than drinking a bottle of wine on the street (…straight from the bottle) because you’re too cheap to pay for one in a restaurant (note to self— I was an embarrassment when I was a broke student…)

What do you do to stay stylish when you’re traveling? Let me know in the comments, I’m always open to more suggestions.

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  • I started to plan out my outfits and try them all on beforehand as well. I love to get on Pinterest for inspiration! It makes getting ready each day so much easier and realizing you have worn every piece you packed is the best feeling.

  • I once wore a dress on a flight home from a trip because it was the cleanest piece of clothing I had left. It was amazing how differently people treated me because of how I was dressed and now I’m way more conscious about how I pack and dress when I travel. It has improved my travel experiences in subtle ways but I’ll never go back to the sweatshirt and yoga pants travel outfit.

  • I totally need to get a hat. I agree they definitely make an outfit look much more put together. The problem I always have with style on travel is that I hate paying for luggage so always try and take as little as possible!! xx

    Jasmin Charlotte

    • Jess says:

      The advantage of having a husband as my travel buddy is that we can split the cost of just one checked bag, which I must admit is very helpful. Yes, if you get a hat, tweet me a pic 🙂

  • Spot on! Couldn’t agree more about watching what’s on your feet. If there is one look I can’t stand it’s running shoes with normal clothes…especially jeans!! I also plan my outfits ahead of time and try rolling my clothes to save space in my luggage. Doesn’t always solve the overpacking problem them…it’s a work in progress! Great tips 🙂

  • Alessandra says:

    Thank you for your tips,they’ve been very useful! I also discovered the power of long skirts: they’re perfect and comfortable for hot weather,rain and also for sunny days if you haven’t your legs shaved 🙂 Why do you hate running shoes so much,even with jeans and a sporty outfit?

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