A Happy Birthday in the Happiest Place on Earth: Disney Road Trip Style

Now, if that’s not the cheesiest headline to ever appear on the pages of The Style Guide, then I’m not sure what is. But it just about sums up this past weekend — I hit the road down to Florida for a great birthday weekend with my family, trekking around Walt Disney World in the process! The Florida sunshine was a welcome retreat from chilly New York City, where I spent a Brooklyn birthday last year (did time really fly that fast!?). The weekend included days spent at Magic Kingdom and Hollywood Studios — a particular Disney World favorite — plus, a topsy-turvy afternoon drinking around the world at Epcot (yes, they serve beer at every “country” within Epcot!). Talk about an action-packed weekend, filled with travel style and just enough warm-weather #menswear to keep me powered up for my return to a cold NYC winter today.

The right casual gear for a casual weekend in Florida. Bring on the sun!

With warm weather on the horizon, I packed up my  Saddleback Leather Rounded Leather Duffel with lightweight gear aplenty, a welcome change from the rugged style essentials I’ve had to break out in the snow around Manhattan and Brooklyn these past few weeks. Unlike my January trip to Philadelphia to see The Killers, it was all about warm weather style, thankfully — so, I layered a Mack Weldon Silver Pique Polo underneath my Life/After/Denim Collegiate Cardigan for a day at the office and a Thursday evening flight to Orlando. As has proven the case with past trips to Florida — including a December Christmas trip — my classic suede chukka boots from Astorflex worked quite well at both the office and the airport. The next time you need comfortable-yet-polished travel shoes, reach for timeless suede chukka bootsOh, and on the denim front? You’ll hardly find a better pair of classic men’s jeans out there than the perfectly faded Abercrombie & Fitch Langdon Slim Denim, a true four-season staple in my book. And if you tend to wear a ballcap when you travel, as I do, there’s really nowhere the casual, well-designed Huckberry Explorer’s Cap can’t go.

Because I like to stick with classic style staples, I also threw on my Timex x Form-Function-Form Horween Leather Weekender — that’s a watch that’ll take you from the office to the airport in casual travel style, no problem. I also had to bring along one of my favorite books as of late, the stellar and moving “Imagine Me Gone” — it’s an emotional read that’ll definitely stick with me, and I can’t recommend it enough. All of that gear left me more than prepared to enjoy a night in Orlando before heading to Disney World the very next day. Still with me? Good deal.

Friday proved a relaxing day to kick off the weekend, with an evening trip to Hollywood Studios on the docket — tal;k about a heck of a fun day! To get around in laidback style and kick off a warm Florida weekend, my trusty-as-ever Huckberry Explorer’s Cap and James Dean Eyewear Aviators kicked off my ensemble on the right note in terms of accessories, as did the Timex x Form-Function-Form Horween Leather Weekender, a stylish short-sleeve Taylrd Clothing shirt and a durable pair of chambray shorts from Canvas by Lands’ End. The combo kept me cool and stylish, while a pair of sporty Frank and Oak sneakers also helped finish off my outfit quite comfortably. From the fast-paced Tower of Terror to the fun-as-heck Rock n’Rollercoaster, Hollywood Studios has long been a huge favorite of mine! It never gets old — seriously! And when you dress well (or try to dress well), that’s quite the way to start off a weekend — delicious dinner at Mama Melrose’s Ristorante Italiano included, too. How could the weekend get better? Well, that’s where a great day Saturday comes into play — at Epcot, no less!

Saturday was a day I’d been looking forward to for quite some time — what’s better than a Saturday at Disney World, after all? Well, attempting to drink your way around the world at Epcot makes it even better, right? A fun day and a fun weekend was made all the better by delicious brews and beautiful weather — even if I couldn’t quite polish off a beer at every stop. In suitably fun and laidback fashion — as seen at the top of the page — I threw on an occasion-friendly vintage “drinks” shirt, featuring recipes of old-school cocktails — it’s a personal favorite when the weather hits the right temperature, to say the least. To stay cool as I hydrated in the heat, my Bridge & Burn Stringer Dune Shorts are a Florida style staple that I always throw on when the thermostat climbs, and Indigo Denim Sneakers from The Hill-side proved more than effective at helping me power through a long day on my feet (just as I wore on my Florida Christmas trip). On my wrist, I had to go with a new-yet-classic standby — the visually interesting Timex x Todd Snyder Blackjack Watch, featuring a neat design and a striking blend of colors, the ideal accessory to go along with a pair of cool Electric California sunglasses. Is there a better way to shield your eyes from the sun while knocking back brews than with a cool set of shades? Hardly. Was the day at Epcot — followed by a delicious Disney dinner in “Mexico” — a smashing success? I’d say it was! That brought the next round of this vacation up — my birthday itself!

Holiday 2017I spent Sunday at one of my favorite places, perhaps the best place (other than Disney or Brooklyn) to spend a birthday — the Wizarding World of Harry Potter! I dressed for the day in a casual graphic tee from Banana Republic, plus my mobile Mack Weldon Active Shorts and my trusty brown leather sneakers from Frank and Oak. I topped it off with my Timex x Todd Snyder Blackjack Watch once again, along with my James Dean Eyewear Aviators — I left my Wizarding robes at home (kidding!), but still enjoyed the day. We capped it off with a delicious steak dinner at STK at Disney Springs, a suitably upscale way to close out the day (for dinner, I threw on my United By Blue Wenlock Chambray Shirt, of course).

Complete with some excellent men’s style gifts from my parents and family (including a few premium tees from Todd Snyder — coming soon to Instagram!), I was more than thrilled to spend an amazing birthday with my family in an amazing place. Spots like Disney World and the Wizarding World of Harry Potter never get old or any less fun — at least, that’s what I think. Are you heading to Florida soon? How are you dressing for the trip? Let me know in the comments!

Check back tomorrow for a new #OOTD post — thanks for reading!


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