Fort Myers Festivities: Celebrating a Florida Christmas

Dressed for Christmas the Florida way. Printed shirt by Quiksilver. Chambray shorts by Canvas by Lands' End. Ripper Sneakers by Reef. Nautical 3-Hand Watch by Jack Mason. Glasses by Frameri.

Dressed for Christmas the Florida way. Printed shirt by Quiksilver. Chambray shorts by Canvas by Lands’ End. Ripper Sneakers by Reef. Nautical 3-Hand Watch by Jack Mason. Glasses by Frameri.

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.

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Gear fit for Florida and NYC. Jack in Indigo Star Shirt by Taylor Stitch. Kinzie Jeans by Mugsy Jeans. Academia Chariot Sneakers by Brooks Heritage. Watch by Timex for J. Crew. Explorer’s Cap by Huckberry. Wallet by Brothers Leather.

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.
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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.

Looking out on a lovely day at Cayo Costa. Brando T-Shirt by Barking Irons. Swim Trunks by JackThreads. Gratton Sneakers by Fronteer. Expedition watch by Timex. Explorer's Cap by Huckberry. Runaway Aviators by MVMT Watches.

Looking out on a lovely day at Cayo Costa. Brando T-Shirt by Barking Irons. Swim Trunks by JackThreads. Gratton Sneakers by Fronteer. Expedition watch by Timex. Explorer’s Cap by Huckberry. Runaway Aviators by MVMT Watches.

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?

An amazing Christmas featuring some great men's style essentials (of course. Vintage-style cotton sweater by Hillflint. Book by Esquire. Chocolate by Toblerone.

An amazing Christmas featuring some great men’s style essentials (of course. Vintage-style cotton sweater by Hillflint. Book by Esquire. Chocolate by Toblerone.

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!

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Comfortable, crisp style essentials. Chambray shirt by Old Navy. Alpha Stretch Khakis by Dockers. Academia Chariot Sneakers by Brooks Heritage. Waterbury Chrono by Timex x Red Wing. Explorer’s Cap by Huckberry. 810 Wallet by Brothers Leather.

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

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Style Suggestion: A Cozy Christmas

Editor’s note: For more Style Suggestions — including what to wear to that holiday party — swing through here.

Breaking news — Christmas is almost here! If you’re a big fan of the holidays, like me, and appreciate a festive atmosphere in the air and lights all around the cityscape (or your hometown), there’s really no better time to enjoy. But thankfully, the holiday also gives everyone a chance to rest, regroup and ideally, actually get home for some time off. Either way, Christmas and the events surrounding it don’t always have a set dress code — it could be a more casual evening of opening gifts with just the family, or a nice party with friends (hopefully, Ryan Gosling doesn’t drop by). So the style suggestion that follows definitely errs on the side of more casual, whether this is on Christmas Day itself or in the days leading up to. Bear in mind — this is just one suggestion to keep things from getting too sloppy, so mix-and-match (and buy) as you please! Note that we’ll cover a more dressed-up Christmas affair right here next week.

The Shirt: Tommy John Ringer Pocket Tee in Heather Grey — $34

This colorblocked pocket tee is a simple but effective upgrade from the pedestrian crewneck.

This colorblocked pocket tee is a simple but effective upgrade from the pedestrian crewneck.

So right off the bat, that price is a bit much more than most might pay for a T-shirt. BUT, bear with — Tommy John certainly seems to be the real deal as far as quality and comfort goes in the undershirt and T-shirt game. And its Ringer Pocket Tee (available in four colors) is soft, stylish and slim-fitting. Crucially, the color at the neck and pocket sets it apart just so slightly from a regular crewneck tee, even when that might be the cheaper option.  It’s these small style upgrades that can add a little thought to your look, and if comfort is part of the equation, it’s key to still look good. However, if wearing just a tee makes you wary, I’d reach for a great chambray shirt instead.

The Sweater: Old Navy Chunky Shawl-Collar Cardigan — $49.50 (When On-Sale)

A rich color and ribbed knit make this a solid house sweater for a cozy Christmas.

A rich color and ribbed knit make this a solid house sweater for a cozy Christmas.

Because it’s the heart of December, we’ll assume it could be a little bit chilly wherever you might be. That’s exactly the time to reach for a well-priced Old Navy cardigan. The burgundy color is a nice, on-trend nod to the season as a whole (although this cream JackThreads Shawl Cardigan could also be a neat, affordable pickup). But in this instance, the thick burgundy knit brings some nice contrast when paired alongside the lightweight T-shirt. As I’ve said time and again, a shawl-collar cardigan is a great, masculine style move that adds some rugged appeal to any outfit. Plus, who doesn’t love a cozy sweater? If it’s too warm out where you are, ditch it (if you’re lucky enough, that is!).

The Pants: JackThreads The Daily Jogger — $49.50 OR Classic Dark Denim

A dark color and trim cut help these wear less like sweats and more like jeans. Yes, you got that right.

A dark color and trim cut help these wear less like sweats and more like jeans. Yes, you got that right.

As we talked about above, Christmas can go one of two ways — more casual, or dressier. In this case, if you’ve got the option to go more laidback yet want to avoid wearing pajama pants, we’re going out on a limb to recommend a pair of tailored sweatpants in a dark color. JackThreads continues to get a lot of things right with its new menswear line, and stylish essentials at low prices like these are why. Again, if sweatpants still feel too casual, a solid pair of dark denim never fails (I’d recommend Mott & Bow, who makes slim jeans like its Hester model with a comfy hint of stretch). If sweats are too hot, reach for their laidback but just as comfy alternative — the well-crafted sweatshort (like these from my friends at Pistol Lake).

The Sneakers: GREATS Brand Royale Chukka — $152 (On-Sale)

Camel plus black in a chukka silhouette = dressier sneakers than the norm.

Camel plus black in a chukka silhouette = dressier sneakers than the norm.

If sneakers seem a silly option for the middle of winter (and they very well might be if there’s a ton of snow), I’d urge you to go with a reliable (but cheaper) desert boot instead. If, however, you’re able to rock some chukka sneakers from GREATS, you’ve found a style choice that fits right in with fall & winter yet feels more comfortable than a thicker boot (note that Reef’s Outhaul Lux Chukka does that, too). The Royale Chukka definitely checks all those boxes, and even more crucially, the camel color plus black sole is a combo that feels a little dressier than a plain pair of captoe sneakers. These sneakers can be worn through the rest of winter in the right weather, and into spring with some lightwash jeans, too — that’s the gift that keeps on giving.

The Watch: Timex Weekender 40mm — $46

A black leather strap and that simple Timex dial create the ideal happy medium for the rest of this outfit.

A black leather strap and that simple Timex dial create the ideal happy medium for the rest of this outfit.

Just as in this site’s Thanksgiving Style Suggestion, a Timex is the affordable watch pick once again. In this instance, Timex’s classic weekender dial keeps the watch more casual, but the black face and slip-thru black leather strap makes it ever so slightly put-together. Yet, it’ll still look right at home with this outfit in terms of color and styling potential — it’s just that simple and versatile. Lest we forget, this watch can be mixed and matched with other NATO straps — that’s like getting a new watch for about $10.

The Socks: Richer Poorer Herald Socks — $12

A small way to pump some pattern into an outfit -- for a low price.

A small way to pump some pattern into an outfit — for a low price.

Whereas the rest of this outfit mainly sticks to solid basics, these socks inject some life into the ensemble in a fun way. And assuming you’ll be kicking around without shoes on for a bit, clean, hole-free socks are a must (truly). Throw in a fun polka-dot pattern in a color that complements the rest of the outfit, and you’re set. The oatmeal color of these socks is also just different enough if you go with a heather-grey T-shirt (or even a blue chambray), and the navy dots complement the cardigan and the sneakers, too. Plus, Richer Poorer socks are springy and breathable — not a  heavy wool set.

While the above outfit might not work for everyone, here’s hoping you do get the chance to kick back in a more casual fashion this Christmas — and when that time comes, I hope you’ll keep some of these picks in mind (because who doesn’t love looking their best all the time?). Think I missed anything? Let me know your picks for the holiday season below!

Ben Sherman US