Gentleman’s Creative Guide to Packing for the Holidays

Dec 19, 2022 | Fashion, Travel | 0 comments


As the holiday season is finally here and your out-of-office has been turned on, it’s time to start thinking about packing for your seasonal travels. Whether you are headed to a rural part of your home state which consists of a local grocery and a gas station, a five-star tropical resort to escape the cold, or a family ski trip out West, it’s important to consider everything you might need to make your trip memorable. To help you prepare for your trip, we’ve gathered a few of our favorite pieces that we rarely ever travel without.

The Perfect Set to Travel in

Perhaps one of the most crucial items to include in your packing plan is a comfortable set to wear on the plane or in the car for those long days spent traveling. Our recommendation is a breathable, light-weight cashmere hoodie and pair of joggers like these from Proper Cloth. Regardless of if you are on your way there or on your way home, comfort is the key to making these days tolerable. 

Milano Performance Knit Jogger
Light Grey Cashmere Hoodie

Packing for the Climate

Considering the climate of your destination is the first step in planning your outfits. Regardless of snow, sun, rain or shine, the golden rule of packing is to never shy away from bringing too many layers. 

If your main concern is whether or not you’ll be warm enough, we recommend investing in a high-quality cashmere sweater, a down-insulated winter jacket, and a hat, gloves, and scarf trio to complete your ensemble. 

This Black Cashmere Crewneck Sweater from Proper Cloth is a comfortable and cozy option that can be worn with a dark pair of jeans for a meet-up with hometown friends or paired with a pair of gray dress pants for your classy Christmas dinner. Packing versatile options that can be worn multiple times throughout a trip help limit the problem of overpacking. 

A down-insulated winter jacket will be your best mate when traveling to the colder destinations this holiday season. This Water Repellent Down Jacket from Ralph Lauren not only keeps you dry and warm but its down-filling makes stowing away on a carry-on or personal item easier than ever.

A warm pair of gloves and a reliable hat and scarf are a few pieces oftentimes overlooked that can make or break your night walking around town. This 3-Pack Knit set from UGG will be sure to keep you warm and won’t let you down on your trip out west this year.

For Warmer Destinations

If you are lucky enough to be taking that tropical destination vacation this holiday season, we haven’t forgotten about you. Your packing strategy for this trip should be to choose light-weight linen and cotton threads that can be compactly folded, leaving plenty of room for souvenirs and gifts to be brought back home. 

For light-weight linen and cotton pieces, our go-to style destination is Proper Cloth which offers staple pieces like this linen pair of pants and button up that can be dressed up or dressed down. 

Proper Cloth Allen White Cotton and Linen Dress Pant
Proper Cloth Baird McNutt Natural Beige Irish Linen Shirt

Don’t forget a pair of sunglasses that you can wear to the pool cabana or on your way to a beachside dinner. Randolph USA offers a variety of shades and lenses like these P3 Round in Skyforce Green that will elevate your look to the next level while protecting your skin and vision from harmful rays.

Luggage + Packing 

Depending on the length of your travels, you’ll need to consider the size of your luggage. For trips shorter than 4 days, you will most likely be able to get away with packing a weekend bag. However, for trips longer than 4 days, you might want to air on the side of caution and bring your suitcase out of storage. If you’re in need of one or the other, we recommend the following options to keep your belongings in place and stowed away when traveling. 

The Bigger Carry-On suitcase from Away can easily fit into the overhead of most major airlines or simply packed away in any car or train. Away’s lifetime warranty makes this brand a fan favorite and their wide assortment has options for everyone. 

Going on a smaller trip? Briggs & Riley Baseline Weekend Duffle Bag is the perfect option for someone who is looking for a sleek and appealing bag that is practical and won’t wear over time. Most designer leather bags that provide optimal style are susceptible to short term wear and tear and are oftentimes priced at a much higher price range. 

To complement your Weekender Duffle Bag from Briggs & Riley, is the Baseline Everyday Essentials Kit. A durable toiletry bag that will hold all your belongings is a necessity and one of our must-haves when it comes to traveling. Stock up on miniatures before taking off and you’ll be glad you ditched the quart-sized Ziploc bag once and for all. 

Traveling for the holidays, regardless of where, can be stressful when it comes time to compile a list of things to include for your trip. From the items most obvious to the pieces frequently forgotten, Gentleman’s Creative is here to ensure you think of it all and spoil yourself along the way. Safe travels and Happy Holidays, Gentlemen.

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