When the holiday season hits, I tend to think back to Thanksgiving and Christmas seasons spent in Michigan — who doesn’t love traditions of years gone by? With those memories in mind, it’s been a fun process the past three years to start new traditions in my parents’ adopted home of Fort Myers, and I always welcome the chance to escape the hustle and bustle of New York City for a warm and sunny Florida vacation. I traveled to Fort Myers last Christmas, and I get back every few months — including a recent visit for Thanksgiving — but it never gets old spending time in the sand and sun (especially when the alternative is dealing with a polar vortex in New York City).  Yes, the holiday season in Florida is always a treat, an adventure and a bit of a sight to behold — palm trees wrapped in Christmas lights looks a bit different. But it was great to be with family and friends, and I brought along as much stylish travel gear as I could pack.

Surviving a frigid day in New York City and capping that off with a flight to breezy Florida is no joke, so I wore gear that could stand up to both challenges (the rest, I packed in my trusty, durable Owen & Fred weekender bag — but you knew that, right?). Of course, my packing list looked a lot different than my winter weekend in Baltimore, but I stuck with the ever-versatile Taylor Stitch Jack in Indigo Star Shirt,for starters. It’s as reliable and well-fitting of a casual shirt you can buy, and it provided a nice bit of contrast to my light wash Kinzie Jeans — they’re the perfect travel denim from Mugsy Jeans.

For the day in NYC, I layered up with the heritage-inspired, ultra-comfortable Todd Snyder x Champion Pocket Sweatshirt, and accented the sporty sweatshirt with my comfortable and casual Brooks Academia Chariot Sneakers. They proved easy to slip on and off at the airport, and I’d wager they’ll work just as well for you the next time you travel. On the accessories front, I found my simple, effective (and unfortunately sold out!) Timex for J. Crew watch provided easygoing-yet-crisp travel style. And throughout my trip, I loved throwing on my vintage-inspired Huckberry Explorer’s Cap, a one-of-a-kind grey cotton flannel baseball cap with a navy felt “H” — for Huckberry, of course. So, that gear helped me make it to Florida in style — and it’s a good thing, as we had lots in store for Christmas weekend.

Getting some quality time out and about on the Florida water was in order for an early Friday boat excursion through the waterways of Fort Myers, from Cayo Costa State Park to Cabbage Key — both scenic islands with ample beach space. I stuck with a combination of gear both new and old, starting with my durable-as-heck FRONTEER Super Gratton high-top sneakers. I wore them on my last Florida trip and found they provided comfort and serious durability. A breathable, vintage-inspired Barking Irons Brando G.I. T-Shirt, courtesy of the New York-based design and apparel company, helped me stay cool on the water. Inspired by infantry T-shirts from the Vietnam era, the little details — like the scalloped hem and raised sleeves — make it a great pick-up. Of course, my JackThreads Swim Trunks were just as needed for the day, with their trim fit and neutral navy color. And my crisp, classic Timex Expedition field watch  on a tough black NATO strap held up more than fine, as did my MVMT Watches Runaway Aviators and my stylish — yet adventure-ready — Huckberry Explorer’s Cap.

With a day of exploration behind us and Christmas Eve ahead, it was time to look to the weekend. I did so with a mix of pieces both tropical-inspired — like my Quiksilver Sunset Tunnels Shirt — and my Canvas by Lands’ End shorts. Those pieces worked easily for a nice Christmas Eve dinner and some much-needed time in the sun. It felt slightly odd to not be bundled up on Christmas Eve as in past years, but some subtly stylish, comfortable black canvas Reef Ripper Sneakers helped me navigate the day in style, as did my Jack Mason Nautical 3-Hand Watch on a warm weather-friendly blue perlon strap. The watch, like the black canvas sneakers, proved just as stylish for exploring sunny Fort Myers as it did for grabbing a few brews and enjoy my family’s traditions — a classic Christmas Eve film and a reading of “The Night Before Christmas.” Doesn’t get much better, ehh?

With a delicious Christmas Eve dinner complete, I went to bed with visions of my #menswear wish list dancing in my head (indulge me, will you?).  I hope you were able to come through with key shopping pick-ups of your own, and I certainly wasn’t disappointed with what Santa left me under the tree this year. I was really lucky to get an amazing vintage Michigan State sweater from Hillflint — it’s a super-premium cotton knit piece that I’ll look forward to wearing on Saturday fall trips back to East Lansing and chilly weekends in NYC alike. I’m also looking forward to breaking out an amazingly high-quality Todd Snyder White Label dress shirt for New Year’s Eve, and I’ll be reminding myself of proper dress etiquette with Esquire’s “New Rules for Men,” a fun, informative and quick-hitting feature from the fantastic pages of the essential Hearst publication. I also snagged a great Ticketmaster gift card from Santa — so you can expect more live music and menswear in the coming year on the blog!  Needless to say, I’m definitely a fan of the Christmas season, and I’m very thankful for such a great day!

Given the need to put together a stylish New Year’s Eve outfit — not to mention those crucial menswear resolutions — I’m sure plenty of this gear will more than come in handy in the weeks ahead. Even moreso than those stellar gifts, it was a day that made me feel very lucky and grateful to spend it with my amazing family — that’s my true takeaway from this Florida trip (and of course, the added #menswear goodies will make it a bit hard to pack up for my flight home).  So with an overstuffed duffel bag packed for later this week, I reached for sharp essentials for another day today in Florida, starting with a classic Old Navy chambray shirt — casual but still crisp. And my Flint and Tinder Pocket T-Shirt proved a comfortable base layer. Because great style doesn’t stop with your top half, I reached for my slim-fitting, easily wearable Dockers Alpha Stretch Khakis and my  Brooks Academia Chariot Sneakers. When the occasion calls for simple style, I’d wager you’ll do just fine with similarly versatile, do-everything pieces like a classic chambray shirt and chinos.

So, what’s on the docket for the rest of the week? Definitely some rest, some reflection before 2017 and yes, plenty of planning for a stylish New Year’s Eve in New York City. You can stay tuned for business as usual tomorrow, starting with a winter style #OOTD, and continuing right on through to what to wear to ring in the new year via Wednesday’s style suggestion. Oh, and if you didn’t enter last week’s men’s lifestyle giveaway, do so before the 28th to win a Dick’s Sporting Goods gift card and get a jump on those fitness goals. At any rate, thanks so much for reading along — I hope you’ve had a stellar holiday season, and I hope you’re ready for lots more menswear on The Style Guide. Thanks, as always, for reading!

-Beau