There’s a certain stretch of year that’s probably my favorite, and no …. it’s not the Governors Ball music festival here in NYC. That favorite time of year would happen to be the holiday season, especially now that I’m further away from my family. I recently traveled to Fort Myers for Thanksgiving, and this past weekend brought me back to down South for a Florida Christmas–that’s on top of a recent early December weekend trip to Orlando and Tampa for the 97X Next Big Thing music festival! Yes indeed, I’ve spent plenty of time down south these last few weeks. In between my recent Florida trips, I went the complete opposite direction, traveling north to Toronto. Rest assured, the Florida sun is certainly much more welcoming. And from trip to trip, I’ve tried my best to bring along my favorite #menswear. Did you dress in holiday travel style this year? As always, I’d love to hear about your own travels over on Twitter. But for now, let’s soak up the sun and head south!

Unlike past trips to Florida, where I’ve had to head right from the office to the plane, this trip gave me the luxury of heading from my apartment onto the plane. So, I packed up my Voyager Waxed Weekender from Boarding Pass NYC (formerly Owen & Fred), and I hit the road! I dressed for comfort and style, throwing on an all-new, super-comfortable Mott and Bow T-shirt, topped off with an easy-to-layer Mott and Bow denim shirt, two stylish pieces that provided comfort and just a bit of casual polish. For even more laidback comfort and mobility, my Proof Nomad Pants, with the construction of a chino and the mobility of a pair of sporty sweatpants, were just the ticket. They teamed more than readily with a pair of classic chukka boots from Astorflex, as perfect a pair of travel footwear as it gets. And to add a bit of visual interest and sharp style, my Timex x Todd Snyder Mod Watch proved effective and reliable. The great part about layering a bit? When I got to Florida, I simply ditched my Mott and Bow denim shirt and wore my Mott and Bow tee! How about that? Point being: The next time you want to head from a chillier locale to a warm one, dress with casual, cool layers in mind — add some mobile chinos, classic chukka boots and a stylish, casual watch.

It’s always nice to get home, get settled and enjoy the beautiful Florida weather — Friday had plenty of that, and it was the perfect segway into a long weekend that proved filled with holiday cheer and relaxation. On Saturday, that meant we enjoyed a relaxing Florida day and an afternoon beach trip, no early wake-up needed! For venturing into Fort Myers, I stepped out in exploration-ready but casual style, starting with my United By Blue Wenlock Chambray Shirt and my Mack Weldon Board Shorts, essential for soaking up some Florida rays. A pair of Reef men’s sneakers proved durable and more than able to take me around town, while my sporty Timex x Todd Snyder Blackjack Watch felt speedy and retro. On the accessories front, keeping my eyes safe from the sun — but doing so in style — was top of mind. My James Dean Eyewear Aviators were my pick, equally classic and modern … plus, well-suited for grabbing a post-beach brew. Days on the water are hard to come by in NYC, as one might imagine, so I relished the chance to get some Florida sun.

Sunday brought with it … well, Christmas Eve, for starters! It’s a Hayhoe family tradition to head to the movies as a family, and after a relaxing morning, that’s just what we did — “The Greatest Showman” was a fun, enjoyable ride . I don’t know if the excitement of Christmas with family will ever quite get old, so I appreciate the chance to keep old traditions going — and of course, I never pass up the chance to dress in style! As seen at the top of the page,  I threw on a casual Banana Republic graphic tee (Cheers!) and paired it up with the Mack Weldon Active Shorts, a frequent favorite when I travel to Florida given the blend of comfort and stretch. A crisp, well-made Timex x Form-Function-Form watch helped me get around in style, featuring rugged good looks and easy wearability — seriously, Timex x Form-Function-Form watches are not to be missed. For striking style and protection from the sun, my James Dean JDS105 sunglasses were the way to go, and classic SeaVees sneakers (in this case, a bright blue take on the SeaVees Hermosa Regatta) proved effective and comfortable on the accessories front. Again, it never gets old when I get the chance to savor family traditions, and that goes for our post-Christmas Eve dinner of shrimp and salad, followed by Christmas Eve presents (pajamas for everyone!) and a traditional reading of “The Night Before Christmas.” After that, off to bed!

Christmas in the Hayhoe household is another tradition I always enjoy — how can you not?? It’s very special to spend the day with family, curled up with great coffee and most likely, a choice Christmas read. We also always enjoy homemade cinnamon rolls and egg casserole. And it’s an important reminder to slow down and take it all in, especially as we close out a busy year. 

I was truly fortunate to receive some amazing gifts, from a Ticketmaster gift card (more live tunes!) to a lovely Todd Snyder dress shirt (seen above!), the terrific book “Manhattan Beach” (by Jennifer Egan) and a classic Orvis belt from my grandparents. Those gifts will absolutely come in handy all year long, and I was so thankful to spend the day relaxing with family in the Florida sun! The trip wasn’t done yet, though. 
Luckily, I had a full day in Florida to take in a last few rays of sunshine in style. I dressed in easygoing, travel-ready gear for the occasion, from my Abercrombie & Fitch Langdon Denim to a Mott and Bow denim shirt. I also layered up for the flight home with a classic Bridge & Burn T-shirt — these new tees are soft, well-tailored and well-made. In short, you can wear these easygoing men’s T-shirts all day without worrying about whether they’ll stretch out. One place you do want a little stretch for both comfort and style? Your jeans. That’s why I reached for my Abercombie & Fitch denim. The A&F denim features a light weight, a pleasingly faded wash and a slim fit — ideal to pair with my classic suede chukka boots from Astorflex. I teamed the combination with my Timex Form-Function-Form Horween Leather Chronograph, a visually interesting watch with a rugged leather strap. I also threw on my reliable-as-ever Huckberry Explorer’s Cap, and finished the look off with stylish sunglasses from James Dean Eyewear.

The next time you’ve got a few hours before your flight, be sure to wear casual style essentials — like a classic denim shirt and stylish suede chukkas that are ready for both travel and adventure in equal measure. As I always say, my trip came to an end much too soon — I always cherish being able to get away from NYC and enjoy time with family, especially during the holiday season. I feel recharged and energized to take on the rest of 2017 and the start of 2018, and I hope you  do, too! More importantly, we’ll have plenty of style content coming at you to get you ready for New Year’s Eve, including a helpful #OOTD that covers, well … what to wear on New Year’s Eve! Look for it tomorrow.

In the meantime, Merry (belated) Christmas and thanks for reading!

-Beau