Whenever I hit the road, I always look forward to packing in style. And when I get the chance to head south to Florida, visit with family and chow down on amazing Thanksgiving food? That’s all the better. Spending the holidays in a warm-weather locale like Florida is a change of  pace from your Style Guide author’s past holidays growing up in Michigan, so the garb I packed with me has changed accordingly over the years. It’s a bit disconcerting sometimes to go from rugged fall style in NYC to spending time on the beach in Florida, but I always look forward to doing so. And just as with my August trip to Florida, I loaded up plenty of warm-weather gear fit for versatile style situations — including Thanksgiving dinner, brewery-hopping and lots of time spent in the sun.

As always with traveling from NYC to a warm climate like Florida, I sought to pack gear that would move seamlessly from a chilly NYC work day to breezy Florida in style. That meant selecting the ever-versatile, comfortable Public Rec Crosstown Bomber— it’s the sort of jacket that layered easily over my classic Old Navy chambray shirt. And my Dickies Slim-Fit Tapered Leg 5-Pocket Pants were more than ready for a day at the office and a flight back home, as were my new CLAE x JackThreads Strayhorn Mid Sneakers. The chukka-style hybrid silhouette and grey wool upper proved stylish for the work day and helped me breeze through security. And, I had to bring along my Timex x Red Wing Heritage Waterbury Chrono for a dash of rugged-refined style for the office and fall travel. On the footwear front, I had to break out my Jack Erwin Cooper Boat Shoes from storage — the next time you’ve got to tackle warm weekend weather in style, you should look to pack a similar pair. Of course, I took along toiletries from the likes of Nivea for Men — the brand’s Creme works as a hand, body and face moisturizer, so it’s a do-it-all travel essential. And throughout my trip, my retro-inspired Nautica sunglasses and the slick, new MVMT Watches Runaway Aviators proved stylish accessory options for the Florida sun. Seriously, never underestimate the power of a stylish pair of men’s sunglasses.  So, with stylish travel gear in tow and a quick flight home in the books, it was onto a fun Thanksgiving holiday weekend.

The day on Wednesday — as one would expect — dawned sunny and pretty hot. With that in mind, I reached for the stretchy, stylish and tailored OLIVERS Apparel Capital Short, as seen at the very top of the page. The versatile color paired up well with another sport-inspired, hybrid piece — a new Heather Merino Knit Polo from performance apparel purveyors QOR. Its tailored look is offset by the merino blend fabric, which wicks sweat and dries quickly. And the comfortable combo paired up well with a new set of kicks — the FRONTEER Super Gratton high-top sneakers, provided courteously by the FRONTEEER team. With their unique design and a silhouette inspired by functional outdoor boots, they’re a nice lifestyle hybrid sneaker. They worked for grabbing a delicious Maple Bacon Donut at the renowned Bennett’s Fresh Roast and hitting the beach. For hitting up Fort Myers Brewing Company later, the brand-new Calypso Watch from the recently launched MVMT Watches Modern Sport collection was a prime, affordable pick. It was also a nice chance to break out a stylish pair of retro-inspired sunglasses from Nautica, and the combination of sport-inspired and functional pieces held up well for Florida exploration — and a few outdoor brews!

And with an enjoyable Wednesday in the books, it was onto an even more enjoyable Thanksgiving. Now, unlike dressing for a casual fall day, our Florida Thanksgiving celebrations required significantly fewer layers than an NYC November day. With that in mind, it made it easy to reach for the Thomas Pacific Latitude Print Shirt, also from Bridge & Burn. Although that shirt is sold out, you can’t go wrong reaching for any of a selection of similar stylish short-sleeved shirts the next time you find yourself in a warm locale for a holiday. The same goes for the ever-classic Taylor Stitch Slim Chinos in Light Stone — any chance you get to pick up durable, high-quality and classic Taylor Stitch menswear (especially the brand’s lauded chinos), I’d recommend you take it. I found the combo worked quite nicely once again with my Jack Erwin Cooper Boat Shoes and the always-stylish  Timex x Red Wing Heritage Waterbury Chrono for eating second (and third) helpings of Thanksgiving dinner.  And the whole ensemble was polished-yet-casual enough for family Thanksgiving — no expandable waistband in sight on those Taylor Stitch chinos, although it would’ve helped.

Of course, Friday presented another absolutely beautiful Florida day, and a prime chance to break out some of my best warm-weather menswear again for a little in-person Black Friday shopping and strolling. (And, let’s be honest — a trip to the excellent Big Blue Brewing was in order). The lightweight, breathable and slim Vesper Polo from the fine folks at Mack Weldon was just what the doctor ordered — and it teamed nicely with my ever-essential Stringer Dune Shorts from Bridge & Burn. It was a bit strange to wear warm-weather gear after a chilly NYC fall, but I adjusted easily thanks to stylish pieces like the always-reliable Jack Erwin Cooper Boat Shoes — they’re the rare type of boat shoe that’s refined, and exceedingly easy to wear for both beachside and city exploration. What’s more, my always-reliable Timex x Todd Snyder Mod Watch had to make the trip, too — I think if you pre-order one for yourself, you’ll be mighty surprised at just how much you’ll be reaching for this casual-yet-versatile timepiece. I’d also recommend you reach for an upgraded, subtly designed ballcap if you need to protect your face from the sun — my Goorin Brothers vintage ballcap (unfortunately sold out now) is a perennial favorite. To snag a similar style for yourself, check out the Huckberry Explorer’s Cap. With that gear in tow, it made for a fun, easygoing day strolling around the neat artists’ village of Matlacha — and if ever you find yourself in the Fort Myers area, Point Ybel Brewing is worth a stop to cap off your day.

And no Florida trip would be complete without a little beach relaxation and a trip to the American Sandsculpting Championship on Fort Myers Beach — right? I made sure to bring along stylish beach gear for some fun in the sun. That gear included the comfortable, sweat-wicking Anything Shirt by Strongbody Apparel, plus a pair of tailored chambray shorts from Canvas by Lands’ End. Of course, my Cooper Boat Shoes helped me out quite nicely for navigating the sand and the city, as did my Nautica sunglasses. If you’ve got to pack relatively light, versatile accessories and footwear that work for multiple situations can undoubtedly help ease the burden of lugging around a heavy weekender bag.

I also switched up my outfit for an evening out and about in Fort Myers (including a requisite viewing of the new “Fantastic Beasts and Where to Find Them,” an excellent Harry Potter film). That meant reaching for a tailored short-sleeve gingham shirt from Banana Republic, along with a pair of tailored Canvas by Lands’ End shorts. I also looked forward to breaking out my crisp white SeaVees Legend Sneakers, a go-anywhere set of kicks that works for both casual and business casual situations. My durable, stylish Calypso Watch from MVMT Watches was once again up to the task — I’ll be getting a ton of use out of that timepiece in the weeks and months to come.  And as to the movie? If you’re a Harry Potter fan, you should absolutely check out the incredibly awesome expansion of the HP universe… but back to menswear, ehh?

It seems that every time I head to Florida, it gets tougher to leave — especially after a great holiday with family and some beautiful warm weather. But with that being said, it was time to pack up to head back to NYC — to deal with the impending cold weather, I again grabbed my Public Rec Crosstown Bomber and the versatile, travel-friendly CLAE x JackThreads Strayhorn Mid Sneakers. I packed up my gear in my dependable Owen & Fred Voyager Waxed Weekender, which has more than capably stood up to the demands of both summer and fall travel across the past few months. Of course, my travel watch pick was an easy one — my Timex x Red Wing Heritage Waterbury Chrono  hasn’t yet let me down! And when it comes time to add to your everyday carry, the Tanner Goods Utility Bifold is a wallet I’d certainly recommend.

So, with that gear in my bag, I hopped a crowded flight back to NYC — and already, we’re back in action and looking ahead to the holiday season. I had an amazing, fun, relaxing and reflective time in Florida — being able to dress in style was just icing on the cake. But you really can’t put a price on time spent with family — can you? What’s more, I’m already looking forward to being back to Florida for Christmas next month. I hope you enjoyed your Thanksgiving in style, and I hope you’re ready for a busy holiday season at The Style Guide — tomorrow, you can look for a seasonally appropriate #OOTD entry, and Wednesday, we’ll tell you exactly how to dress for your next holiday party. Beyond that, you can expect the best menswear on tap with our Style Pick of the Week series, and more holiday men’s style ideas galore.

Thanks so much for reading — stay stylish!

-Beau