How to Look Fly When You Fly: The Ultimate Travel Style Guide

Looking slick on the road just got easy.

Travel Wardrobe Staples

Maintaining slick style while traveling is no easy feat. Every trip has different demands, and seamlessly transitioning from day to night can be a headache. And that’s to say nothing of making sure what you bring is easy-breezy to pack.

Happily, there are some travel staples that reliably mix comfort with panache. Better yet, these items will work with pretty much any travel adventure — whether you’re lying on a dock dipping your fingers into the blue-green waters of the tropics, hailing taxis in a thriving metropolis or sipping wine on a cobblestoned patio.

Pack these fashion-savvy items, and staying fly on the go will be a snap.

Tee Up

There’s a reason they call it a classic.

We’ve been wearing t-shirts since the 19th century, when the U.S. Navy began issuing them as undergarments. Simple shades — black, grey and white — in soft jersey cotton with different cuts and neck shapes go with anything and can be worn multiple times without anyone noticing. Switch up the look by adding horizontal stripes with elbow-length sleeves and boat necks.

Vintage concert tees with raglan sleeves can be great, but be strategic about your logo tees. And keep the sweat-wicking fabrics for the gym — Under Armour is for working out. Period.

The best thing about tees? You can roll them up and slide them into the in-between spaces of your suitcase without worrying that you’ve packed too much.

A Better Jacket

A blazer can take the place of a bulkier jacket and elevate your style at the same time.

Whatever your gender, look for blended fabrics — like cotton and linen — that move easily from day to night with an unstructured cut and a sleeve that you can roll if you want.

Walking through SoHo? Throw the blazer on over your hoodie. Dinner reservations in Hollywood? Wear a slinky tank underneath. Tie a scarf around your neck one day and wear a collared shirt the next.

Guys are wearing blazers with shorts for a suit alternative, and women are pairing them with ultra-feminine dresses to give them an edge. Boxy or fitted, it’s up to you.

Hoodwinked

A good zip-up hoodie is the ultimate in versatility.

Throw it over your workout gear on your way to the gym, over your sunburned shoulders after a day at the beach or layered underneath your blazer for warmth. Add it to a dress, or to a shirt with a tie.

Zip it up to your neck for an early morning hike and tie it around your waist to ward off the early evening chill. And be sure to wear it on the plane for a cozy flight.

Buy it in the snuggliest fleece or the softest cashmere; the material is up to you.

Not into hoodies? Switch this item out for an equally adaptable cardigan.

Down, Not Out

This one is a no-brainer. For guys, this one shirt can be worn untucked with the sleeves rolled and only a few buttons fastened, or buttoned to the neck with a tie and worn under a blazer or hoodie.

For beach days and the tropics, try linen. Grab denim with pearl snaps no matter where you’re headed, because that combination has been cool since Steve McQueen. Pack a short-sleeved button-down in a slim fit with an ironic print to switch things up.

Ladies look just as good in the denim version, and an oversized white button-down looks great with a slim leg (hello, Audrey Hepburn). Keep an eye out for the button-down shirtdress with pockets. Wear it over tights with ankle boots or go bare-legged with sneakers. And don’t forget to grab your blazer.

Easy Breezy

From silk camisoles to sequined spaghetti straps to your basic t-back, the tank is the crux of a woman’s wardrobe. For the boys, a tank is an essential casual item worn with shorts or a cuffed pant and rubber slides (sandals with a high strap). But you could also layer a tank under a close-fitted button-down or narrow blazer.

A black tank literally goes with anything — wear it out to dinner and then to the gym in the morning. Rinse it in the sink, hang it to dry and do it all over again.

A caution for men: While a wispy tank showing lots of skin can work for women just about anywhere, no one wants to see the wider expanse of your chest over dinner — keep the deeper cuts under wraps with a jacket while you’re eating.

Keepin' it Casual

If you’re a jeans person, bring two pairs in different cuts and washes. Try vintage button-fly Levi’s with a straight leg, and your favorite pair of skinny blacks. (Pro tip: Keep the frayed edges and holes to a minimum. It’s a look, but it doesn’t have to be the only look.)

Women, if you think you can make do with a single pair of Levi’s, swap out that second pair of casual pants for wide-leg Palazzos.

Dressed to Impress

Dresses are a go-anywhere addition to your travel wardrobe, and eliminating the need to figure out what goes with what is a packing bonus.

Try a floaty mid-calf floral, or a close-fitting cut in a solid color. Both can both be paired with sneakers to take you all over town.

You can wear a dress over your swimsuit during the day and throw some dry underthings in your bag to change into post-swim. Switch out your shoes, freshen up your makeup, add some jewelry and you’re evening ready.

Women win in this category with the ease of a one piece — they also have the option of a romper — though you should consider a loose fitting look overall, rather than something you have to struggle with in the bathroom.

Guys, you might feel like a romper isn’t for you, but why not experiment? Try a long-sleeve in a solid color cotton — black is best for the beginner. Cuff your pant legs and pair it with slides during the day, and wear it with your boots at night. It could work. If not, keep in mind that overalls are making a comeback for men this season.

Get Shorty

Even if skirts aren’t normally your thing, they are perfect for pulling together a polished travel look. For a woman on the go, a tea-length pleated skirt with casual sneakers and a tucked-in tank is the sweetest thing. A shorter A-line with pockets pairs well with ankle boots, as does a high-waisted wrap.

Shorts take a little more thought. Everyone loves a good pair of cutoffs, but they’re harder to take from day to night. It is possible, though. Pair them with your blazer, boots and a white tee. Black shorts with a pocket, or dolphin-style shorts with side slits and rounded corners, look great with a diaphanous long-sleeve or silky button-down.

For the guys, a straight-cut cotton short with a pocket can be worn during the day with a classic tee or button-down. Add your blazer and your ankle boots and you’ve got a reservation-worthy ensemble, just like the ladies. Don’t forget to throw a pair of workout shorts into your bag, too. Just know that, unfortunately, it’s not as easy for you to transition them into a going-out look.

Hella Tight

Both ladies and gents (trust) should consider rolling a pair of lycra Lululemons into their suitcases. Wear them in the street as a bottom layer against the cold, in the gym because they’re comfortable or while making your way through the wilderness to guard your legs against wayward branches. Tights are also a comfortable option for long flights. (Be sure to grab some with side pockets so you can keep your phone and flight info handy.)

Guys, if you aren’t comfortable on, ahem, display, just throw those workout shorts over top.

If tight isn’t your style, consider a slouchy version of the yoga pant with a fitted cuff at the ankle. This version is even easier to multi-task with. Go with basic black and you’ll be able to wear these to dinner with a tee or tank and the ubiquitous blazer.

Bag it Up

The hip pouch might be making a comeback (they’re calling it the belt bag), but the cross-body bag never left. Make sure it’s big enough to hold your passport, phone and a souvenir or two; a saddle bag is the perfect shape to carry these items.

Distressed leather in shades of cognac or oxblood will never go out of style, while bright reds and buttery yellows make a statement. All of these pop against black.

Lace it Up

For those of you who like to hit the gym when you travel, it’s best to find something that’s casual but functional for training, like a classic New Balance or basic black Nikes.

Leather is always a good option because it can be wiped down after that walk through a medieval village. Stan Smythe’s are a staple, but keep in mind that these don’t have to be your granny’s tennies. Don’t be afraid to make a statement.

Like Shower Shoes, But Cool

Shower shoes might seem like an unnecessary extravagance, but you should consider these babies instead of your traditional thong flip-flop. Rubber slides generally have more support and put less stress on your calves. You can throw them on around your room and add them to a dress just as easily as you can wear them with socks and casual pants.

Plus, they’re hot right now. For all genders.

Made for Walking

For the boys, the brown leather brogue or the wingtip dress boot, like this one in walnut leather from Dalton, is a must-bring. The decorative perforations (or broguing) are their own accessory when showcased against a shorter pant leg. If this feels like too much, choose a Chelsea boot instead. It’s easy to slip on with just about anything.

Ladies, choose a leather close to your skin tone to elongate your leg, rock out with studs and buckles, or go crazy with patterns. Be willing to experiment.

A word of advice: Resist the urge to choose too high of a heel — something blocky will be easier to manage and more versatile. Whatever you choose, stuff socks in the toes when packing them so that they keep their shape.

Summer Fun

Never leave home without a cute suit. This season, it's all about pastels and prints for the dudes and shirred floral-print bikinis and structured polka dots for the ladies.

Lots of suits can also be paired with other items for a fun daytime look. A strapless bandeau top makes a great layer under the straps of an apron dress, and a henley style one-piece is the perfect topper for vintage Levi’s or a full peasant skirt.

Top It Off

Hiding from the sun calls for bendable straw. Beanies are a great fix for breezy temps and beadhead. Just roll them up and shove them in the toes of your boots with your socks to keep their shape.

If you are someone who prefers a wide-brimmed felt or something with more structure, never fear. Wait until your suitcase is full, then dig a hole in the center and carefully place the bowl of the hat upside down in the space you’ve created. Fill it with toiletries in a ziplock bag. The brim will sit flat across the top of your things and the hat will keep its shape. Still worried? Nothing screams commitment to style like a hat box. Just make sure it has a strap you can sling over your shoulder.

Now that you’ve got the staples, everyone should consider adding a couple of pairs of shades in different shapes, scarves to tie around your neck and shoulders, and some signature jewelry. Don’t forget a pack of butt wipes and an umbrella! (Those two things are not related.) You can use the wipes on your entire body as a quick refresher, and a retractable umbrella will protect you from the sun as well as the rain.

And ladies, nothing switches up your look more than a bold eye or bright lip, so be sure to pack a great makeup palette.