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Cyrus A. Schiller is a 26 year old writer from Maryland currently living in New York City.
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I love it when the days get shorter and the temperature begins to dip because, in my opinion, fall is the best season for men’s style. This is the time when you can begin to layer your clothing and experiment with a rich palette of textures and colors. All of these options are great, but when you’re traveling having too many options isn’t always the best thing. What do you pack? How can you get the most out of the least number of pieces? What else do you need to bring?
Fortunately, we’ve got some pointers, so that you always feel great and look put together no matter the time of year (but particularly this fall). The time spent not worrying about what to wear is time that can be better spent getting the most enjoyment out of your trip. And to that end, these fall travel essentials will definitely serve you well on your upcoming getaway.
Lightweight Sweater
With the air getting cooler, it’s time to break out the sweaters. Cashmere is a great fabric that has the twofold advantage of being both lightweight and insulating, making it perfect for the fall. As an added bonus, the soft hand feel guarantees all-day comfort.
It’s easy, however, to be taken aback by the premium good quality cashmere commands, not to mention its spotty environmental record and ecological costs of cashmere mass production. J. Crew, through its partnership with the Aid by Trade Foundation’s Good Cashmere Standard, has you covered with a great sweater that’s easier on both the wallet and the planet.
We especially like the brown coffee herringbone model for the versatility it offers. For a stylish fall trip, you’ll want a good middle layer for dealing with the temperature swings, and this sweater looks fantastic layered over a shirt, on its own, or underneath a sport coat.
Travel Atomizer
When taking a short trip, many guys may not bother to pack a fragrance. But whether you’re attending a wedding or off for a weekend in the mountains with someone special, you’ll want an unforgettable scent that rises to the occasion.
For travel, you’ll want something that can fit in your luggage with your other belongings, and not run afoul of TSA rules on liquid containers. You also don’t want something that, heaven forbid, might leak or spill while you’re on the move, and ruin your day or that of anybody unfortunate enough to be in the vicinity. For these reasons, leave the original bottle at home and transfer some of its contents to an atomizer, like this one from Yeejok.
Flannel Sport Coat
If you haven’t already, start being the guy who goes out in a sport coat. Plus, fall presents a perfect opportunity for wearing stylish outerwear. Quilted jackets, waxed cotton jackets, corduroy jackets, leather jackets, and tweed jackets are all staples of this season. But for traveling, you want one jacket that can do it all – and this flannel sport coat, with its Glen plaid pattern, should check all of the boxes. It instantly smartens any ensemble, while never being too stuffy.
Leather Weekender Bag
A good leather duffle bag can hold more than just one weekend’s worth of personal belongings on the inside—it can hold a lifetime’s worth of travel memories on the outside. Every scuffed, well-loved duffle tells stories far richer than its contents. This piece, the Bennett Winch Weekender from Todd Snyder, is sure not only to be a faithful companion for your next weekend getaway, but if properly cared for, a faithful companion for life.
While lower quality bags compromise with less durable leather and brass-plated hardware, this bag will outlast and outshine them all with its full-grain leather and solid brass construction. Bennett Winch’s weekender not only makes a great carryon for your upcoming trip, but a fantastic heirloom piece that is well worth the investment.
Denim Shirt
There’s a pattern here—and it’s not the one in the sport coat. Fall is a season of change, and a versatile garment is key. You can’t change the weather, but you can weather the change. Nothing on this list is more foundational to a classic fall look than a denim shirt. Whether you wear it on a warmer day on its own or on a cooler day layered with the sweater or sport coat, this rugged fabric is stylish and dependable in just about any scenario.
Classic Sunglasses
Although the days are getting shorter, you still should be protecting your eyes just as you would in the summer. For the fall season, you’ll want a classic pair of shades that pairs well with the rest of your outfit. For travel, we especially like the classic Ray-Ban Clubmasters, as the instantly recognizable browline frames are well-suited to a wide range of face shapes, and will never be out of place regardless of the formality level.
Stanley Travel Mug
Staying hydrated while traveling is especially important, but nobody likes having to buy bottled water in a pinch, both because of the money and the plastic waste footprint. That’s why we think it’s important to choose something reusable.
This Stanley mug has a leak-resistant cap that will keep everything else in your bag clean and dry, while the BPA-free stainless steel body makes it both durable and safe to drink from. The mug is also easy to clean and can keep liquids hot for up to seven hours, or cold for between 10 and 30 hours. So, consider this your jack-of-all-trades drink container. With its solid construction, lifetime warranty, and great style you’ll wonder how you ever got by without it.
Travel Shave Brush
Just because you’re traveling, doesn’t mean you should necessarily default to what is fastest and easiest. Slow down and enjoy the present moment for your entire trip, including when you have to shave. By going with the traditional wet shave, your skin will thank you, and your face will shine with a youthful luster and without razor burns.
Mühle, a heritage maker of high-quality wet shaving products from Stützengrün, Germany, has a variety of beautiful shaving brushes, razors, bowls, and accessories, but we especially like their Chrome Silvertip Fiber Travel brush. With its striking chrome handle and sleek German design, this is the Audi (or BMW or Porsche) of shaving brushes.
The bristles on this particular model are made from a proprietary synthetic that perfectly mimics the feel of a premium badger brush, so that you can enjoy a smooth, luxurious, cruelty-free shave. Once you lather up and treat yourself to a proper wet shave, you won’t want to go back to the recurring expense, subpar performance, and wastefulness of plastic cartridges and disposable razors.
Classic Men’s Umbrella
If you’re anything like me, you’ve probably had fits of frustration where you’ve wondered if there’s such a thing as an umbrella that isn’t a complete piece of junk. Fortunately, there is, and you can say goodbye to those anguished days of ducking into a drugstore and impulse-buying a shoddy umbrella that you’ll either discard or lose within a few weeks. Take advantage of your upcoming trip as an opportunity to upgrade your everyday items and reduce unnecessary clutter.
Don’t think of this umbrella as a cheap, transactional nuisance that you’ll throw out after a few uses, but as an investment in a high-quality, refined accessory that sticks out in crowds and rain showers alike. For your trip, be ready for anything by carrying a good, stylish umbrella, and you’ll never need to make an angry detour to the drugstore again.
“Perfect Pour” Travel Flask
After the travel atomizer, this is the second entry on this list for carrying a small quantity of alcohol, only this is for drinking and not for misting. A good travel-sized flask can be a delightful enhancement to a wedding party, a quiet evening by the campfire, or any special occasion in between.
Stainless steel is used for most flasks, since it is durable and and doesn’t affect the taste of the spirit inside. However, in order to create a truly distinguished flask for special occasions, we teamed up with the English Pewter Company to create a 2oz, HSS-branded flask in pewter, the traditional material of choice for flasks.
Pewter is a highly workable alloy of tin, copper, and antimony that is well-suited for engraving and which develops a patina over time, making a pewter flask a wonderful hand-me-down statement accessory. The one downside of pewter compared to stainless steel is that it does leech flavor when in contact with alcohol for too long, so it’s best to not leave anything in the flask for more than three days. But since three days is just enough time for a short trip, consider a flask with your best spirit when the occasion calls for it.
The Bottom Line
Anytime you travel, it can be difficult to take inventory of what you need to bring. Likewise, even getting dressed every day can be a challenge when you have so many options. It’s easy to feel overwhelmed and to instinctively rely on what is most familiar and convenient. But this can result in more clutter, an overstuffed travel bag, a more rushed and stressful routine, or more wasted money in the long run. A “less is more” and intentional approach to packing is always a good idea.
Thanks for reading and have a great trip!
Cyrus Schiller
Cyrus A. Schiller is a 26 year old writer from Maryland currently living in New York City. After recently leaving a corporate role, he is dedicating himself to travel, writing, and volunteer work, and will be teaching English in Sri Lanka. He first became interested in men’s style during a trip to Italy at the age of 19, where, as a disheveled college student, he observed firsthand how well dressed Italian men are. Cyrus earned an MA in Journalism (Cultural Reporting and Criticism) from New York University in 2021, and in his spare time can often be found at his local Zen temple, where he helps run the mobile food bank and takes martial arts classes. In addition to collecting new and vintage men’s clothing, he sings in a medieval sacred music choir and enjoys exploring numerous other intellectual, musical, and artistic interests.
Edited by Rachel Butler
Photography by Rob McIver
