Holiday Travel Made Easy: Men

Holiday Travel for the Modern Man

Everyone can use a little help packing -- especially around the holidays.
Everyone can use a little help packing -- especially around the holidays. (Image: iStock Photo)

The holidays are stressful enough without the pressure of packing properly, and a lot of men simply aren't up for the challenge. Some of them try to stuff all they can into a bag, only to find that they don't wear half of those items. Others may pack bulky clothes, or outfits that don't fit the weather. Bad packing can lead to extra bags, which can mean extra baggage fees and more worries about the airline misplacing the bags.

So, sacrifices must be made in the packing process, but not at the expense of your sense of style or your comfort. Packing smart and planning ahead takes some of the stress and pain out of the holiday equation.

When you think about what you're going to be doing, it gives you a better sense of what you're going to need, and you shouldn't pack for anything more than that.

Jeremiah Brent, interior designer


The first step toward packing efficiently is identification of those elements of clothing that you won't need during your trip.

"I used to be one of those people that overpacked and would have four suitcases for three days," says interior designer Jeremiah Brent. "But I've gotten much better because I realized that when I traveled, I was packing a ton of things and not wearing half of them."

When in doubt, remember two simple words: versatility and layering.

"I take the two pairs of jeans that I always wear," Brent says. "We all have a drawer full of jeans, but realistically you have one pair that you wear all of the time, and I bring some basic T's."

While jeans and T-shirts may not sound like classic holiday fare, Brent says they serve as the bedrock for an entire wardrobe. He can wear a black T-shirt with dark jeans, dress shoes and a blazer for a dressy outfit, or wear the same shirt in a casual outfit.

You never know when the need for formal attire may arise. While you can't pack for every contingency, you can apply the rules of versatility and layering to even the stiffest aspects of your wardrobe.

"No matter where you’re traveling for the holidays, it’s always a good idea to bring a suit," says Natalie Fisher, part owner of Life:Styled, a "boutique lifestyle management firm."

"For both planned and last-minute formal affairs," Fisher says, "the entire suit can be worn together, or it can be broken down for more casual events."

Weather Adjustments

It's important to pack for the climate you're flying to and the weather you might encounter there.

"Before you start packing, think about the trip and how you want to feel," says Niki Leondakis, president and COO of Kimpton Hotels & Restaurants. "Do you want to feel casual and comfortable around your family, or do you want to feel festive, or perhaps formal? Whatever the case, pull clothes from your closet that best reflect how you want to feel while participating in holiday activities."

Fisher recommends taking into account the mood and atmosphere of your holiday events when you pack.

"Yes, it may be 30 below outside," Fisher says. "But do you plan on spending the majority of your time drinking scotch by a fire in the family cabin, or will you be heading to various work or social functions outside of the home?"

Once again, start with a solid foundation, and from there work your way up — or down, depending on your destination.

"Cold or hot is easy to work around, so I think about what exactly I'm going to be doing," Brent explains.

On a recent trip, Brent knew he was going out a few nights and that he'd be working with paint during the day. He had to have options for both.

"When you think about what you're going to be doing, it gives you a better sense of what you're going to need, and you shouldn't pack for anything more than that," he says.

Leondakis suggests laying out all of the clothes you think you might need to use on the trip. She also suggests you organize them by potential outfit combinations.

"Once you’ve laid it all out," she says, "walk away for a while, and when you come back to it, you’ll find you don’t need all of the items you’ve laid out."

Cold weather gear like hats, vests and boots add bulk to luggage. Being selective is important.
Cold weather gear like hats, vests and boots add bulk to luggage. Being selective is important. (Image: Getty Images)

Packing and Dressing for Departure

What you wear on the trip also matters. You can ease some of your packing issues just by wearing something useful on the flight or ride.

"Travel in jeans and or boots if you're traveling somewhere you'll be using these, because they’re always the heaviest, but they can also be dressed up," Leondakis says. She advises picking out some of your favorite items and wearing a couple of layers, starting with a light top and a sweater for warmth. You may tie the sweater around your shoulders or waist if you don’t need it, she noted.

Fisher says the "ultimate airplane travel secret" is the pullover sweater.

"The pullover sweater is to men as the scarf is to women," she said. "It can easily be worn when it inevitably gets chilly, but can just as easily be stuffed in your carry-on should you get warm, and can be quickly layered over a simple T-shirt or worn underneath a winter jacket."

Brent prefers to dress up for flights. He said that even though you will spend most of the vacation with loved ones, you still may need to make a good first impression somewhere on the trip.

"I always say don't dress (poorly) when you're going to the airport," Brent said. "You never know who you're going to meet or who you're going to sit next to. I know people that have met their husbands on an airplane."

Always pack a pullover for holiday travel.
Always pack a pullover for holiday travel. (Image: Getty Images)

Travel Tips for Men from a Frequently Flying Woman

As president and COO of Kimpton Hotels & Restaurants, Niki Leondakis oversees more than 50 North American hotels and finds herself on the road 75 percent of the year. This has made her a packing virtuoso, and she has plenty of advice for men traveling for the holidays. Her first rule is do not pack gifts in the luggage.

"Traveling during the holidays usually means crowded airplanes and not a lot of elbow room," Leondakis says. "It could also mean having to squeeze gifts into your luggage, bulking up your otherwise concise packing methods. If you can ship your gifts to your destination ahead of time, that will help free up space immediately, and you'll find that it's invariably cheaper than paying an exorbitant checked-bag fee."

Leondakis says heavier items, like shoes and shaving kits, should be placed at the bottom of the suitcase or bag. This is a two-fold strategy.

"Placing footwear in shoe bags ensures they don’t get scuffed or (mess up) other items in your suitcase, and air pressure can cause even the most air-tight toiletries to leak," she says. "The last thing you need is hair gel leaking all over your suede shoes and dress clothes."

Finally, she said, pack only lightweight, easy-to-wash workout gear.

"If you like to exercise on the road, pack lightweight tops and bottoms that can be sent to the hotel laundry or washed in your sink," she explains. "I recommend Nike Free sneakers because they're lightweight and flatten down for packing. They don’t take up as much room as your typical sneakers."

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