My friends, as you very well know … this past weekend was Thanksgiving! And that brought with it another chance to venture down to my adopted home of Fort Myers for an excellent long weekend with family (and another classic Style Guide road trip, of course). I was last in Florida for a Memorial Day weekend visit — and my folks also made their way north this October — but Thanksgiving in Florida is always a special treat, combining the traditions of family and home with beautiful weather (as I’ve found out these past few years). With my parents moved into a new house and the promise of a lovely weekend, I hit the road on Tuesday in prime fall travel style — of course, if you follow me on Instagram, you probably saw how I dressed for Thanksgiving in style. And if not, today’s the prime chance to dive in! Save me a second helping of turkey, will ya?
My trip began in earnest on Tuesday afternoon, as I jetted out of work early hauling my favorite men’s style essentials, starting with the handsome, durable WP Standard Large Messenger Bag. From trip after trip — down to Nashville and out to Portland — it’s proven a durable, effective way to haul my everyday carry, and that was certainly the case here (including the latest issue of Gear Patrol for some in-flight reading). For a day at work and a quick cab ride to the airport, my Flint and Tinder All-American Jeans were reliable and comfortable, yet work-appropriate — as was my Flint and Tinder Texas-Made Oxford, a well-fitting shirt that perfectly nailed business casual style. The next time you’ve got to get to a flight from the office, I’d also suggest you throw on a pair of classic Astorflex suede chukkas — as I’ve written about before on the blog, they combine comfort, sustainability and effective style in spades. The combination was versatile and casual, perfect for an evening arrival in Florida and a few brews with a delicious home-cooked meal. With that, it was onto the rest of a long and very enjoyable weekend!
After a surprisingly quick and relaxing flight, this Thanksgiving weekend was off and running. Any trip to Florida is always an excellent excuse to break out standout casual style – for a relaxing Wednesday around Fort Myers, that meant reaching for a Grayers striped polo and versatile cotton-blend shorts from Reef, plus my trusty-as-ever Jack Erwin Cooper Boat Shoes (always a warm-weather favorite). Reef’s shorts do a more-than-serviceable job when it comes to offering mobility and comfort, perfect for getting around Fort Myers. I complemented the look with classic aviator sunglasses from James Dean Eyewear – is there a better icon to emulate when it comes to ultra-stylish sunglasses? I’d say not, especially when it comes to battling the Florida sun.
I also threw on my reliable Huckberry Explorer’s Cap and the sharp Electric California Carroway Leather Watch, a consistent favorite for travel and everyday style. The next time you find yourself needing to dress in casual style for warm weather, step into versatile shorts, a striped polo and leather boat shoes that are more city-ready than dock-friendly. It’ll pay off! With that combination, I was more than ready to keep my vacation going.
Although the weather sure is different in Fort Myers than my home state of Michigan when it comes to Thanksgiving, it’s just as enjoyable and fun-filled to celebrate Thanksgiving there – so I had to dress for the occasion accordingly. And the traditions stay the same, from watching the Macy’s Thanksgiving Day parade to enjoying plate after plate … after plate of family recipes. I opted for style that was crisp and polished, yet breezy. Enter a tailored Todd Snyder dress shirt – a Christmas gift from my parents last year! – plus a comfortable, mobile pair of Banana Republic’s Rapid Movement Chinos. Believe me, that extra stretch came in handy after a few helpings of Hayhoe family Thanksgiving.
In the footwear department, I stepped into a pair of classic Sebago Legacy Penny Loafers, a Florida-ready option that offered dressy style and a bit of comfort in the heat. To cap off this tailored-yet-laidback ensemble, a stylish leather watch from MVMT Watches proved dressy, sharp and yet appropriate for the occasion. On the eyewear front, the new Esquire Oliver Sunglasses from Liingo Eyewear have been a favorite these past few days – courtesy of the brand, I’ve been testing out a new pair with excellent results! These glasses are simply designed, well-made and just a bit refined – ideal to wear on Thanksgiving, don’t you think? My #menswear look gave me just enough versatility and comfort to enjoy a relaxing day filled with delicious food and great times with family – that’s what it’s all about, I’d say.
I still had quite a bit of time to savor a relaxing vacation in Florida, too. So, on Black Friday, I took not to the mall or the Internet – alright, I definitely did do some shopping – but to the water! Enjoying the Florida sun is something that, well … you simply can’t do in New York City too often, so I relish the chance to hang out by the pool as much as possible. For the occasion, I packed a pair of Mack Weldon Board Shorts, my reliable Huckberry Explorer’s Cap and some pool-ready Reef Rover Low sneakers (not to mention my trusty James Dean Eyewear aviators). Does anything top relaxing by the water with a refreshing brew? Over Thanksgiving weekend, no less? There’s not much better, man.
Saturday brought with it the start of a beautiful Florida weekend – definitely warmer than NYC, to say the least. A highlight of the day? Watching a winning effort from my beloved alma mater, Michigan State University, as they beat Rutgers to close out their college football season. With a family full of Spartans, from my grandfather all the way down to me, it’s a welcome treat to take in a great game – and I did so in style with my Tailgate Clothing team shirt (which I’d also recommend you wear to your next football tailgate).
My breezy Bridge & Burn Stringer Dune Shorts helped keep me cool, while my Johnston & Murphy Allister Sneakers were a team-friendly pair of footwear (Go White!). And to suitably cap off my ensemble, I positively had to put on my Jack Mason team watch – they’ve got a plethora of options, likely including your favorite team. What better way to cheer on your alma mater? Yet again, it was another banner Saturday in Florida – yet, the weekend still wasn’t done!
Luckily, I had a final day of relaxation in the Florida sun! My take on casual Florida style started with a pair of DSTLD Slim Jeans in Light Wash, which have served me quite well week after week this fall season. I also threw on a casual, easygoing Abercrombie & Fitch Garment-Dye Oxford Shirt, as reliable a stylish travel shirt as it gets. I complemented the look with a stylish leather watch from MVMT Watches, plus my comfortable and travel-friendly Astorflex Greenflex Chukkas, once again. And for dependable travel style hauling my everyday carry essentials, I had to reach for a stylish weekender bag in addition to my WP Standard Large Messenger Bag .Of note: My pick of choice this time around was my dependable Voyager Waxed Weekender from the revamped Boarding Pass NYC — formerly Owen & Fred! As expected, the entire combination helped me get around with style and durability in mind (but not before some excellent Florida brews and bites).
It was — once again — a trip that was over too soon, but no matter how many or how few days I spend with my family, it’s always refreshing and energizing to get away from NYC and enjoy a lovely holiday. I already feel like Christmas in Florida will be here sooner than expected. And as it were, I’m actually headed back to Florida this coming weekend for the 97X Next Big Thing music festival! I positively can’t wait to take in some great tunes and see my sister once again. In the meantime, we’ll have you covered when it comes to all things #menswear this week, including a new #OOTD and plenty more.
Thanks for reading, and I hope you enjoyed your Thanksgiving!