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.


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.

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!


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!


NOV CAMPAIGN: Photo of multiple shoes on white background with logo (border)


#OOTD: How to Dress Down a Summer Blazer

Editor’s note: You’ve surely seen this hashtag lots of different places, including on Instagram. But how does that carry over to real life? The #OOTD will take one great item and put together a versatile, stylish outfit around it. Look for past features here.

As we’ve talked about in past #OOTD entries here on The Style Guide, summer style — particularly at this point in the season — can be a bit tricky. Perhaps you feel you’ve exhausted all the ways to wear shorts in the summer that you can think of, or maybe you’ve even tired of styling linen pants in the heat. But, that’s where summer also works out well. Since it’s warm, you get a bit of leeway when dressing. And that means you can put together stylish combinations that are also unexpected. Those khaki suit trousers? Break them up from the rest of your suit. Throw in style staples that should already be in rotation — like a classic navy blazer — and you’re set with an #OOTD that works for traveling in warm weather or waltzing to Sunday brunch. Oh, and a great polo is also a must-have. But where to get all this great gear? Look no further than the below ensemble — and follow along on Instagram to get more daily styling tips (if you feel so inclined, that is).

Mashing up your favorite style essentials, from a crisp summer polo to a classic blazer and comfortable slip-on sneakers.

Mashing up your favorite style essentials, from a crisp summer polo to a classic blazer and comfortable slip-on sneakers.

The Polo: Mack Weldon Vesper Polo, $68 — Yes, it’s true: The brand that makes your favorite long-sleeve merino tee is here with a new polo that’s crisp, well-tailored and made from very breathable micro-mesh knit fabric.

The Blazer: Grayers Cayman Blazer, $104.98 — At just more than $100, this blazer is a heck of a deal, made from 100 percent cotton and featuring Bemberg-lined sleeves (that’s the good stuff, FYI).

The Pants: Canvas by Lands’ End Stretch Chino Suit Trousers, $89 — Just when you thought you could only wear suit pants with a suit, along come these versatile chino trousers cut with a hint of stretch.

The Pocket Square: White Edged Linen Pocket Square, $10 — A sharp navy blazer deserves a crisp white pocket square cut in a summer-appropriate weight, and at $10, this thing’s a steal.

The Sneakers: SeaVees Hawthorne Slip-on Standard in True Navy, $78 — A pair of classic white sneakers would also work here, but the navy plays nicely off the powder blue polo.

The Socks: Sock Genius Villa Park No-show Stripe Sock, $10 — The same spot you hit up to snag that pocket square can also hook you up with comfortable, stylish no-show socks for a nice deal.

The Watch: Armogan Spirit of St. Louis Chronograph, $225 — A sporty-yet-stylish polo calls for a  slick watch inspired by the world of aviation, and the navy blue strap plays handsomely off the crisp white dial.

The Sunglasses: Sunski Madronas Sunglasses, $39.98 — Simple is sometimes better when it comes to great style, and that’s the case with these durable and very affordably priced shades via Huckberry.
Buck Mason - Timeless Design. Made in America.
Putting together an outfit when you’ve been dressing for the warm weather for a few months needn’t be all that difficult, even if at first it sounds taxing — especially when you’ve got pieces that combine subtle style efficiently. The base of the outfit is the same thing you might wear on the weekend — stylish slip-on sneakers — yet the other pieces, like the sharp polo and the navy blazer, are more suited to the work week. Yet in tandem, the combination works because the colors play well off each other and the overall ensemble — slightly sporty yet stylish — is very well-suited to summer. It’s going to be hot, and a breathable polo and cotton blazer work well together. Chime in with an #OOTD suggestion of your own at The Style Guide Facebook page in the meantime.

Do you own a new Mack Weldon polo yet? Would you style it with a navy blazer, or ditch the jacket and keep it casual?

The Friday Read: How to Style A Blazer, American-Made Watches & Taylor Stitch

Editor’s note: Expect these posts once a week on Fridays — consider this a jumpstart on reading for your weekend downtime. Expect a mix of style and non-style content. For more entries, click here.  

Although all weeks go by particularly fast around these parts, this past week was one for a bit (just a bit) of reflection amidst the hustle and bustle of NYC. I had the chance to catch up for some delicious patio brews and oysters with my good friend Clay Chambers of Brothers & Craft, who just returned from some momentous time abroad at menswear trade and runway shows in London, Paris and Milan (and in fact, you can catch more on Clay in a Style Guide Q&A).  We took the time to catch up, to chat menswear and to take some time out from the grind — we find ourselves in different places a lot, but always reconnect. It’ was a great reminder to slow down every so often and take life in stride (even if the scenery is a bustling New York sidewalk). That helped cap off a busy week indeed, and I’m even more excited to finish off the work week with a special night at Daryl’s House Club (just a quick train ride from NYC), seeing one of my favorite groups of all-time, Lucius.  Their music definitely reminds me to slow down and take things in, and even if it’s my second time seeing them, it should be just as special. I hope you get the chance to take some time, relax and enjoy the weekend — but not before checking out the Friday Read below (wink, wink).

  • The ever-stylish team at Valet offers up 4 tips on how to style a blazer this summer; some of those combinations are absolutely perfect, don’t you think? (Editor’s note: For more tips on how to rock a blazer, click here).
  • The equally style-minded team at Gear Patrol reports that American watch company Weiss will be launching the first watch featuring an American-made movement in a long time.
  • Non-Style Note of the Week: We  all love some Starbucks, right? Well, there’s a chance they could be underserving and overcharging you — a case is headed to court claiming that Starbucks is overcharging you for smaller lattes; not exactly a great value, ehh?

On the lookout for more style content?

  • The team at Taylor Stitch is back at it again with the seriously sturdy Transit Duffel — get all the details via my latest post at GearMoose.
  • Add another collection to your list of “must-do” shopping — the Canvas by Lands’ End line is packed with style essentials, as I found out in writing a brand profile for the great team at The Manual!

Lastly, thanks as always for reading, and enjoy the weekend,


Buck Mason - Timeless Design. Made in America.

Style Suggestion: How to Dress for A Summer Wedding

Editor’s note: For a range of style suggestions covering everything up to and including Sunday brunch, click here.

Perhaps you walked out to your mailbox one day and found it waiting for you. Or, it popped up on your fridge in the winter, and you forgot about it. Or it was buried under a pile of paperwork until now. What might that be? The summer wedding invitation, of course. Always fun, always an adventure — and always a concern as to what to wear. Lest you scramble to find an outfit (or dash out to rent a suit that might be poor-fitting), rest assured that we’ve got you covered here today. Preparing to both travel in style while also bringing along a proper suit to deal with a (likely) hot climate is a tricky endeavor — and it might be here sooner than you think. While we’ll cover travel style upgrades in the coming weeks, perhaps the most pressing part of things is covering what you’ll wear on the day itself. If you’re in the wedding party, hopefully the groom took some wedding style tips seriously. If you’re just focused on the bachelor party… I wish you luck. The below scenario covers what to wear if you find yourself merely along for the ride in a hot environment. If you’re not ready yet, hopefully you’ll be in tip-top shape by the end of this post.

The Suit: Canvas by Lands’ End Chambray Suit Jacket — $289 AND Chambray Suit Pant — $99

The ideal summer suit from an unexpected brand.

The ideal summer suit from an unexpected brand.

If you haven’t heard the name Lands’ End in a while, or given the site that much thought, think again. The newly revamped Canvas by Lands’ End line plays off the more contemporary, style-forward look and feel of the old Lands’ End Canvas line, and in this case, that’s a very good thing. For just about $400, you’re getting a slim, modern chambray suit that should be lightweight, breathable and ready for warm weather. The color is a nice alternative to a standard navy (although that would also work), and you can choose either hemmed or unhemmed pants in a range of sizes. When layered right, the jacket could even work into early fall with paired with a slim crewneck sweater.

The Shirt: Lawrence Hunt Standard Dress Shirt in White — $65

This is no ordinary dress shirt -- performance fabric is built-in under the arms.

This is no ordinary dress shirt — performance fabric is built-in under the arms.

Lawrence Hunt is another brand that sometimes inspires some questions when the name comes up. Whereas other brands stick to traditional dress shirts crafted from heavier fabrics, Lawrence Hunt takes everything you thought you knew about dress shirts and upends it.  That’s right — the brand’s Standard Dress Shirt in White blends 100 percent cotton with moisture-wicking, anti-bacterial, 4-way stretch fabric; in fact, it’s even designed based on athletic performance wear. So this is one dress shirt that can truly keep you cool no matter how hot it gets. It also comes with button or cufflink options depending on how dressy you want to go.

The Tie:  The Tie Bar Navy Knit Tie — $25


The always-reliable, never-unstylish navy knit tie -- worth the price now and down the line.

The always-reliable, never-unstylish navy knit tie — worth the price now and down the line.

The classic navy knit tie comes into play time and again in outfits across the style spectrum (and particularly this site) with good reason. It’s nearly the perfect four-season tie, what with subtle texture that stands up to a thicker wool blazer in the winter and adds some visual contrast and weight to a textured chambray suit. That’s the goal here, as it’ll stand out subtly against the crisp white dress shirt while also offering a change of pace in terms of color. At $25, it’s pricier than past Tie Bar pick-ups, but all the more worth it if you can get use of it across four seasons.

The Pocket Square: J. Crew Factory Linen Dot Pocket Square — $14.50

Just as reliable as the navy knit tie, and perfect for summer in terms of pattern and texture.

Just as reliable as the navy knit tie, and perfect for summer in terms of pattern and texture.

Just as with the classic navy knit tie, a pindot pocket square like this one  is fail-safe in regards to summer style. The linen fabric falls in line with warmer temperatures, the pindot pattern stands out nicely against the texture of the tie and the suit, and it helps break up your chest visually without being too overpowering. At just under $15, it’s a solid deal for a brand that’s gotten a heck of a lot like J. Crew, its stylish older brethren. This pocket square can even be switched into a khaki blazer when you’re back at work following that wedding.

The Shoes: M.Gemi The Strada Derby in Sand Suede — $248

A terrific visual complement to a chambray suit this summer.

A terrific visual complement to a chambray suit this summer.

Have you heard of M.Gemi? They’ve gained some notable traction in the past few months with the introduction of its men’s line (a feature on will help with that), and they’re continuing to pick up steam. The Strada Derby is just among a set of offerings — including dress shoes and sneakers — being done by the brand, but the Strada perhaps fits best for a summer wedding in a hotter climate. The Derby-style open lacing and the sand suede are both casual yet crisp (for something dressier, you could grab the Tappo Brogue). Sizes can be limited and the price is an investment, yet you’re getting a really versatile shoe that can pull double duty even when traveling to said wedding.

The Socks: Mack Weldon Total Eclipse Stripe Socks — $12.50

A win-win -- stylish socks that are breathable and comfortable.

A win-win — stylish socks that are breathable and comfortable.

While some are partial to rocking no-show socks with a suit (particularly for an outdoor wedding), rocking longer socks might be in the cards for some of us. And if you’re going to be pulling on extra fabric around your ankles, best make it fabric that’s breathable, moisture-wicking and comfortable — that’s where the Total Eclipse Stripe Sock comes into play. The navy stripes play nicely off the tie and the blue chambray, too.

The Belt and Watch: J. Crew Leather Dress Belt — $68 AND Timex Weekender Fairfield Watch — $75

Simple, stylish essentials that mesh with the other colors in this ensemble.

Simple, stylish essentials that mesh with the other colors in this ensemble.

So, we’re going with a belt that’s nearly as expensive as the watch itself? In this case, yes. If, like your author, you find yourself wearing brown shoes frequently, investing in a slim, classic leather belt like this J. Crew option is in the cards. Because those shoes are suede, matching up directly with the belt leather isn’t needed. And because the Timex Weekender Fairfield Watch is in the same color family (generally) as the belt and shoes, it works out. Plus, at a casual outdoor wedding, things are more, well… casual.

The Sunglasses: Warby Parker Batten Sunglasses in Jet Silver — $145

A reliably stylish frame shape and a cool color to pair up with the other shades of blue in the outfit.

A reliably stylish frame shape and a cool color to pair up with the other shades of blue in the outfit.

It wouldn’t truly be a late spring or early summer wedding if we didn’t suggest a pair of sunglasses to combat the intensity of the sun. Warby Parker was among the first innovators in going direct to consumers digitally, and their designs are (for the most part), clean, classic and stylish. The Batten Sunglasses are no different, and the cool  blue shades strike more than a passing resemblance to a certain secret agent’s sunglass of choice.

While the above outfit might at first glance look to have a lot of moving parts (everything from sunglasses to a pocket square to a watch to a tie are up for consideration), it’s all about making refined pieces work for your environment. A crisp white shirt and navy knit tie works across all four seasons, but the upgraded shirting fabric should definitely keep you cool. Reaching for a chambray suit from a brand on the rise also helps maximize budget and style concerns in equal measure. And those suede shoes? Well, if looks are any consideration, they could very well become a go-to pair the rest of the summer. Shop on, and let me know of any pieces you’d consider swapping out!

How are you dressing for any summer weddings you’ve got coming up? Would you switch out any pieces above?

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