Heading to the beach on vacation? Flying to a ski resort? Wondering what to wear? Regardless of where you’re spending your hard-earned time off, remember this: YOU are on vacation; your personal style is not.

Vacations are a time to relax, have fun, recharge, experience something new or revisit a beloved place. Vacations are not a time to take a vacation from looking good. 

Looking good on vacation does not mean wearing the same things you wear in your normal life. Vacations are a time to try something new with your clothes.

“That's the one time that you can kind of let your hair down and try something different. Nobody's gonna see you again,” Joanna Medeiros, a Taelor stylist, said with a laugh. 

Scott Shapiro, another Taelor stylist, agrees. “A vacation is a good opportunity to kind of try new things. You’re on vacation, and it's like, ‘why not?’ Step out of your comfort zone,” he said.


Choosing vacation clothes? Ask for help

Every Taelor customer gets a personal stylist. Joanna urges her customers to reach out early in the vacation-planning stage. Because unless a guy is particularly stylish by nature, it can be challenging to find a new outfit ideas for vacation.

“Don’t do this on your own,” she says. “It really is a partnership. And I want to make sure I'm sending my guys the things they need for vacation.” 

The idea is to find new, boundary-pushing clothes that guys will actually enjoy. “I want them to be able to wear clothes that look good and make them feel comfortable on vacation,” she said.

Depending on the type of vacation you choose, your clothing needs will change. But there are some key concepts and must-have items for your vacation destination. 


Men’s clothes for vacations in the snow and cold

“If you're on a winter vacation like a ski trip, it could be a fun time to try different things with knitwear,” Scott says, noting that a vacation is a time to move beyond hoodies and crewneck sweaters. “Maybe a chunky crochet sweater in a color you wouldn't normally do, maybe with a wintry motif on it.”

A key to successful dressing for vacation is to ensure you have clothes that are built for the weather. If, for example, you live in Southern California, you may not own a puffer jacket. But if you’re invited to hit the slopes in Canada with friends, you’re going to need one. 

Melissa Slavick, another Taelor stylist, says one of the things she likes most about Taelor is that the company doesn’t put its clothes in storage when the seasons change. “When somebody tells us ‘Hey, I'm going on a ski vacation,’ we still have puffer coats and winter jackets we can send them,” she said. “We even have liners that can go under, if they already have a puffer coat. Then we also have sweaters for the days you're bundled up inside.”


Male attire for summer vacations, beaches and tropical locales 

Heading to the islands? It may be time to be colorful and whimsical. 

Melissa says Taelor keeps lots of such trending items on hand for when customers hear the call of the sea.

“We know our customers are going to need short-sleeve or sleeveless options when they go on winter vacations to a tropical destination,” she says. “So we have these lightweight pieces, shorts, and the tropical prints they want when they're going to the Caribbean or someplace like that.” 

Those tropical prints in particular are a good choice when heading to warmer climates in the dead of winter, according to Scott. “A tropical vacation is time to experiment with fun prints and colors. They just feel vacation appropriate,” he said.

Pair a printed, colorful button-up short-sleeve shirt with khakis or a pair of chinos to complete the outfit and look put together. But if you're not comfortable with loud and colorful prints, don’t just wear those same solid-color shirts you wear to the office. Instead, find a print in muted colors that match your personal preference. Adding a print is a good way to take a small step out of your everyday wardrobe and try something new. You can add white sneakers for a casual look or sandals if you are relaxing in the sun. Your Taelor stylist can help you find a vacation outfits that work for vacation and work for you. (See our men’s clothing rental plans here.)

It’s worth remembering that not all summer-style clothes will work when you’re traveling to the beach.

Linen shirts, for example, are wonderful for hot climates. But linen is prone to wrinkling. Putting it in your suitcase may not be wise.  “Unless you ask for linen, I probably won't send it to you,” Joanna says. “ It does not travel well. Unless you bring a steamer on your vacation, it won’t work for you.” (For more about linen shirts, read our other article, “Why Linen Shirts Are a Must-Have in Men's Fashion”)

Instead, discover more vacay looks that keep you cool and stylish, such as vibrant floral prints, chic loungewear, classic denim shorts, and trendy wide-leg pants.  Explore these must-have pieces now on!

Tips: try pairing navy pants with a lighter or brighter blue shirt - BILLY BELT LIGHT BLUE DENIM BUTTON UP SHIRT

How do I look good when traveling? Try Out a Monochromatic Look to Impress for Vacay Photos 

Another way to up your style game is to play with different shades of the same color. Monochromatic dressing always looks good in photos and will make you look put together when you capture all those great vacation moments. This approach to choosing a resort wear is less stressful, too. You do not have to think about what goes well together. You can assume that if it fits in the same color family, then it's a match. For example, if you are new to this, try pairing navy pants with a lighter or brighter blue shirt. 

Some go-to vacay looks our stylists recommend include: 

  • Wearing shorts with a short sleeve henley shirt, will add a bit of polish to a basic outfit duo.
  • Wear a short sleeve chambray top with cream-colored shorts. This color combo is classic, but always feels fresh.
Men wear a short sleeve chambray top with a light colored shorts.


Relax before and after your vacation. Rent your clothes instead of buying

The next time you plan a vacation, consider renting your clothes from Taelor to get more options for what to wear. By renting clothes instead of buying them, you don't need to spend a fortune. Moreover, returning from a trip usually entails the hassle of laundry; but with Taelor, you can just send back your items by dropping your worn clothes in the provided prepaid envelope at the hotel's front desk, conserving luggage space and eliminating the burden of cleaning. Make traveling a breeze, and start your subscription with Taelor today! 

A male model opens a box from Taelor with different shirts in it

By Paul Conley