41 Cute Travel Outfits To Wear On All Your Getaways (2024)

Classy and Cute Airport Outfit

Look like an off-duty celebrity for the airplane in skinny black jeans, a soft black tee, the essential camel coat, aviator sunglasses, and a casually draped soft neutral scarf. Be kind to your tootsies, and wear with sneakers or flats.

Maxi Skirt and Striped Top

Create a chic outfit for stylish travel destinations, by tucking a black and white striped top into a floral print maxi skirt. Add black and white accessories, as pictured, for a striking, modern effect.

Button Down and Shorts

Your office button down can do double duty on vacation as a beach cover up, or smartly take the place of a cardigan sweater with jean shorts and tank top outfits, as pictured here.

Soft Pants and T-Shirt

Soft pants may be the best thing to happen to travel fashion since the invention of the airplane. Pack a pair in your suitcase to wear with your swimsuit, crop tops, and basic t-shirts, as seen here.

Polka Dot Maxi Dress

Dress up for evenings out on your European vacation in a long, playful polka dot dress. Wear with summery accessories, as shown here.

Unstructured Neutral Blazer

If you're packing jeans and a tank top, add a neutral colored blazer to your bag, for an easy and chic top layer. We're big fans of the unstructured style seen here, which looks dressier than a cardigan.

Black, White, and Chic All Over

Fit in with the locals when you travel to Europe in the fall or winter, by layering a chic black and white striped sweater over classy wide-leg black trousers.

Red Jumpsuit

We are huge fans of the jumpsuit for "one and done" dressing. A red jumpsuit looks great on its own, dressed up with a statement necklace, or a big summer hat, and helps you stand out from the resort crowd.

Button-Down and Jean Skirt

A white button-down shirt is a great addition to your vacation capsule wardrobe, since it can be styled in so many different ways. Here, it dresses up a distressed denim mini skirt for a day of city sight-seeing.

Floral Romper

What's better than a fun floral romper for the beach? You can wear it as an easy swimsuit cover up, then add a cute pair of shoes and some jewelry for dining al fresco. A fedora-style summer hat adds style, too, as seen here.

Little Black Dress

Pack a little black dress in your travel bag and you'll never be without a cute going out outfit. Play with accessories to style it in different ways. On cooler nights, a black leather jacket or a fitted black blazer makes a stylish top layer.

How to accessorize a little black dress

Essential Travel Outfit

Three easy pieces create one chic outfit you can wear on the plane, for daytime, and out to dinner, simply by changing your accessories. Your favorite jeans, a simple white top, and a long black cardigan or unstructured blazer — it's as simple as that.

Gingham Dress

A gingham print dress is just meant for wearing in summer, while you stroll along the boardwalk eating ice cream. Style it with wedge sandals and gold jewelry, as pictured, to give it a cute update.

14 fresh ways to wear gingham print now

Black and White Beach Outfit

Cut a charming figure in a black and white outfit for wearing to the beach, and out for co*cktails or dinner afterward. A black ruffled off the shoulder top matches perfectly with summery white jeans, and your favorite beach bag.

White Top and Denim Skirt

Create a cute casual outfit in snap by tucking in a white tank top with a short denim skirt. Fashion an all-American color scheme if you like, by adding a red square scarf at your neck.

Floral Maxi Dress

A floral print dress is a must-have when you travel in summer, not least because you can just pull it on and go. If you have a few seconds to spare, add a pretty wide brim hat, as seen here.

Extra Large Blouse and Black Pants

An oversized blouse is not only super fashionable for wearing with slim black pants, it also allows for air flow on hotter days. Add a pair of trendy white shoes and keep jewelry to a minimum with this look, as the blouse is already extra.

Jersey Dress

A jersey dress rolls up small for your suitcase, and can be dressed up or down, depending on where your vacation day or evening takes you. Try a wrap style in a pretty pastel hue, as shown here.

White Maxi Dress

If you'll be going out to dinner on your trip, pack a long white dress that you can wear anywhere. Make it super fancy with a white blazer and heels, or keep it simple and chic with flat sandals and gold jewelry.

Dotty in Black and White

A flirty white polka dot skirt looks adorable for dinners out, matched with a simple black off the shoulder top or bodysuit.

Navy Blazer and White Jeans

Be the classiest one on the sight-seeing tour, and head straight to dinner, in a fitted navy blazer, skinny white jeans, and your cutest sandals.

14 chic ways to wear skinny white jeans

Off the Shoulder Top and Ankle Jeans

Look cute and classy for any travel destination, in flirty white off the shoulder top and perfect-fitting ankle jeans. Add a trendy leopard print clutch, as pictured, and wear with strappy nude sandals for a long leg look.

Pink Romper

Rompers are great for wearing on vacation, since you can simply pull on one piece and go. A belted pastel romper shows off your shape, and is a summer favorite, with neutral accessories.

New York City Outfit

Travelling to New York, or another fashion capital? Mkae like a local by styling a fashionable outfit with your athleisure pieces. Track pants look polished, when you add a trendy leopard print sweater, and stacked heel ankle boots that are easy to walk in.

See 10 more stylish ways to wear the athleisure trend

Belted Mini Dress

Add a bright skinny belt to a simple sundress, for a pop of color and to highlight your waist.

Summer Scarf and Jean Shorts

A big summer scarf is the star of this easy travel outfit, with a tank top and denim shorts.

White Blouse and Soft Pants

Here's another cute way to wear the essential soft pant for travel, with an equally soft white blouse, and cute neutral accessories.

Here are more cute, easy outfits for summer nights

Colorful Skort and Floral Top

Create an easy, cute summer outfit with a colorful skort (there are shorts under there!) and a trendy dark floral top. Wear with black sandals as pictured, a colorful clutch purse, and optional summer hat.

Belted Maxi Dress

Take a summery floral maxi dress to the next level, by cinching it with a waist-defining belt. Wear with this year's must have red boots, and a black leather jacket as the weather requires, for a trendy spring or fall travel outfit.

Sporty White Outfit

White shorts, a white t-shirt, and white sneakers make a great beach day outfit. Add a white blazer or navy cardigan, and maybe a big cuff bracelet, and you're all set for the co*cktail hour.

Waterfall Cardigan and Jeans Outfit

This may be the most foolproof airplane outfit ever. A waterfall cardigan looks great layered over a loose-fitting shirt and skinny jeans. Make it extra stylish by adding a statement necklace, a great tote, and open toe ankle boots, as pictured.

Summer Dress and Cardigan

Layer a pretty pastel cardigan over a lightweight summer dress, for easy daytime style. Wear it with ankle boots for evening, or flat sandals for a day of walking.

Get ideas for styling a cardigan sweater

Stripes and Jeans

You'll look casually cute in any city, from Paris to New York, dressed in classic stripes, and comfy relaxed jeans. A cardigan tied around your waist looks stylish, and is good planning, too.

Fall or Winter Travel Outfit

If you're heading somewhere a bit chilly, stay cozy in an oversized sweater in a neutral shade, worn over skinny black jeans. Add a big, soft scarf in a contrasting color, to add even more warmth (and visual interest) to your outfit.

Longline Vest and Leggings

Dress up an easy leggings and t-shirt outfit by layering on a longline vest, which gives you coverage and helps to pull together sporty separates, dressing them up for shopping trips into town.

10 cute ways to wear leggings

White Top and Black Pants

Who ever said minimalist style had to be boring? You'll fit right in with the French girls in a simple, stylish outfit of a soft white blouse, nice black jogger pants, and neutral ankle boots. Add a moto jacket, when the weather is cool.

Striped Dress

Stripes are so cute for summer in pretty ice cream pastels. Wear a classic striped dress with a denim jacket for day, then swap in a black blazer and add a statement necklace for going out at night.

Ruffled Maxi Skirt

A tiered maxi skirt will look great with all your travel tank tops, especially in a versatile black and white polka dot print.

See more ways to wear polka dots

Leather Skirt and Sweater

A leather skirt is a chic alternative to black jeans for colder locations, and can be just as versatile in your travel wardrobe. We like how this blogger has styled it, with a soft pastel sweater, nude heels, and a ladylike chain bag.

Belted Romper

Belt a solid-colored romper to define your shape, when you're taking a daytime tour. Be sure to wear flat shoes when your day will include lots of walking.

Black Maxi Dress

A black maxi dress is a vacation must-have, whether you're taking a beach vacation, or traveling to a major urban destination.