So, welcome back to another Style Guide travel post! It’s become a custom these past few years for me to make a spring trek down to Florida in mid-March, right around the Big Ten Tournament (featuring my beloved Michigan State Spartans) and right around my dad’s birthday (hey, Dad!). And so it was the case again this past weekend, as I got out of the hustle and bustle of New York City for some birthday celebrations with my dad and some much-needed Florida beach time. I had the chance to spend a week down south as I celebrated a Fort Myers Christmas in style back at the end of December, but this trip couldn’t have come at a better time, what with cold temperatures returning to Brooklyn this past weekend. My packing list was different than my recent winter trip to New Haven, but I focused on spring style essentials and my favorite #menswear picks for the road nonetheless. Join me, and bring that bottle opener — will ya?
It was a temperate early morning in NYC as I hit the road, so I had to dress with transitional travel style in mind. For me, that meant an Abercrombie & Fitch Garment Dye Oxford Shirt, layered up with my Levi’s Trucker Jacket. Of note, that oxford is a very affordably priced, great-fitting and seasonally appropriate shirt. Just as with my New Haven road trip, I stepped into my extremely comfortable, slim-fitting and travel-ready stretch twill pants from Kit Culture — the five percent stretch proved perfect for a plane ride. Equally perfect for travel style? A sharp pair of sustainably made Astorflex chukkas — the Greenflex in Dark Khaki provided a stylish contrast to my Timex for J. Crew watch,. And with its minimal case size and durable NATO strap, the latest Timex for J. Crew timepiece is an affordable casual watch you should buy as soon as you can. To haul the rest of my gear, I relied on both the Owen and Fred Voyager Waxed Weekender and the Owen and Fred Flight Brief in Midnight ; each proved stylish and durable, what with handsome leather accents and a canvas exterior.
With my travel gear in tow and nothing but sunny skies in the forecast, I landed in Florida looking forward to some serious fun in the sun — and that’s certainly what you get in Fort Myers. With a delicious lunch at Summerlin Jake’s in the books — waterfront view and all — it was high time for an afternoon spent at my parents’ pool (one of the more scarce things to find in New York City, truly). Topped off with a delicious dinner and some choice brews at The Grill in Fort Myers, it was a much-needed day of relaxation that couldn’t have worked out any better.
With a fun Thursday in the books, a weekend of kicking back was really just getting started. That’s not to say it wasn’t busy — and that’s not to say I didn’t dress in style, either. Naturally, I had to grab warm-weather gear from perennial Style Guide favorites JackThreads, including a nautical-striped tee. Hot temps also meant it was time to ditch my classic blue denim (finally!) for a pair of Bridge and Burn shorts. For exploring Fort Myers, I also had to reach for stylish accessories (enter my Nautica Square Sunglasses) and comfortable, versatile footwear — that’d be the Brooks Heritage Renshaw from the brand-new Brooks Heritage Grand Slam Collection. For grabbing donuts at the legendary Bennett’s Fresh Roast, the extra comfort provided by those kicks was crucial — as was staying on time, thanks to my Timex + Todd Snyder Military Watch. And wouldn’t you know it, keeping track of the clock helped us squeeze in some much-needed beach time before a great home-cooked meal (I’d highly suggest you ask me for my dad’s rib recipe). MSU’s Big Ten Tournament loss aside, it was a heck of a nice day to be in Fort Myers.
As the sun rose on Saturday, it hit me that I still had two full days left in Florida — that’s quite the treat, and it made it all the more enjoyable to get out and enjoy more sun on Saturday. As you’d expect, I tried to make it a point to bring along my best spring bar crawl gear . For stops at the seriously cool Bury Me Brewing (themed like a craft beer graveyard) and a quick pint (and tasty chicken wings!) at The Lodge, pieces like my Life/After/Denim Marco Polo proved well-crafted to beat the heat. I kept things equally casual on my bottom half, opting for a new pair of the Dockers Premium Washed Khaki in a mobile Slim Tapered fit. Featuring washed stretch twill and a Florida-friendly shade of light blue, I’d opt you reach for a similar pair when you want to look put-together, yet feel casual and relaxed.
On the footwear front, the crisp Brooks Heritage Renshaw was again my pick, not least for the way it added a bit of sharp style to the combo. And for getting around Fort Myers and heading to evening dinner at the terrific Courtney’s, my MVMT Watches Calypso Watch and MVMT Watches Runaway Aviators proved to be prime accessories picks. Given the cold weather that swept through NYC this past weekend, I was more than happy to have some ample outdoor time sipping on tasty craft beer and wearing my favorite new warm-weather menswear. Not bad, ehh?
Even with Saturday in the books, I still had nearly a full day in Florida prior to my evening flight back to chilly New York City. So, what else to do but grab comfortable, casual style essentials? For yours truly, that tends to start with a well-fitting tee — is it any wonder that Todd Snyder x Champion T-shirts fit the bill perfectly? And what better way to soak in some sun than with the tailored-yet-casual Ace Short from Mack Weldon? Of course, I find that SeaVees sneakers are the perfect way to complement a casual outfit, especially the spring-ready Legend Sneaker Regatta. And to take on a great lunch at Big Blue Brewing, there were no better picks than my MVMT Watches Calypso Watch and MVMT Watches Runaway Aviators, along with my Huckberry Explorer’s Cap. Unfortunately, the day drew to a close all too quickly — with slightly chillier temps in the forecast, it was time to trade in my Mack Weldon shorts for stretch twill pants and swap my sneakers for chukkas.
It’s always such a treat to head down to Florida and get some great time in the sun and sand — even if it’s only for a quick weekend. The chance to catch up with family and celebrate my dad’s big day was fantastic, too. From the beautiful beaches of Fort Myers to the great craft beer and food scene downtown (and throughout the city), this trip really had it all. Of course, we’re back to the grind today in NYC (follow along on Instagram to see how I’m fighting the chill). With that being said, I already can’t wait to get back to Fort Myers. In the meantime, you can check back here tomorrow for a new St. Patrick’s Day menswear ensemble, and you can join us on Wednesday for a look at what to wear for March Madness.
Until the next trip — thanks for tagging along!