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The sun sets on a crisp fall Saturday in Grand Rapids. View courtesy of my friend Chris’s apartment.

As I explored the lovely city of Grand Rapids this past weekend, I was struck by how lucky I am to have lived and grown up in such a beautiful state, and to have such great friends. The opportunity to travel back is, of course, not lost on me either.While it was tricky to balance working from Brooklyn and hopping on a flight back to Michigan after a whirlwind week of Timberland-centric press work, I did indeed manage to make it in one piece! And it was truly a great time in Grand Rapids, the home of famed festival ArtPrize and also some decent brews (to say the least). This was all in spite of the fact that I was greeted, in characteristic Michigan fashion, by a bit of brisk weather. Luckily though, I had proper style gear on-hand to brave the elements.

Stumbling upon cool murals was a highlight in a city known for its burgeoning art scene. Slim denim by Mott & Bow. Grey jacket by JACHS NY. Sunglasses by Randolph Engineering. Leather chukkas by Timberland. Dive watch by Invicta

To get home, my Satchel & Page Slim Mailbag and Navali Weekender were  more than durable, yet that wasn’t my primary concern! Packing gear to beat the cold while also in transit was the bigger ordeal– how to pack light yet layer up and stay comfortable? Answer: A terrific pair of Mott and Bow denim with stretch built in,  plus some solid outerwear. It’s pieces like these that can make your travels a heck of a lot easier in terms of comfort (UNIQLO also offers somed nice stretch denim at a different price point). To complete my travel get-up, I went with a striped J. Crew henley — always a rugged style suggestion for fall — underneath a quilted yet surprisingly lightweight down coat from JACHS NY. The jacket was comfortable to get around the airport and not too hot — it would be a good travel pickup as you look to bundle up and hit the road this holiday season.

Just a look at some of the cold-weather gear I packed, including my Reef x H.D. Lee workshirt, Iron & Resin gloves, American Trench merino watch cap and black Reef chukka sneakers.

Complementing my travel outfit were my trusty Timberland Coulter Chukka Boots — I’d also recommend you pick up a nice pair of leather chukkas for fall. To say they go with everything – even a T-shirt and jeans – is an understatement. To keep things simple packing-wise, I opted just to bring one watch — my ever-reliable Invicta 8926 Pro Diver (still ticking!). However, I loaded up on a few pairs of comfortable and stylish American Trench socks, plus my nice watch cap from the brand. The cap was a huge help, and though I had hoped it would be temperate enough to forgo them, my Iron & Resin gloves also proved invaluable in the cold.

Exploring Beer City U.S.A was a highlight. Workshirt by Reef x H.D. Lee. Slim Travel Jeans by Bonobos. Navy henley by United By Blue. Merno watch cap by American Trench. Black chukka sneakers by Reef. Glasses by Warby Parker. Photo credit: Jesse O’Brien.

To get around Grand Rapids, I layered up in a nice, insulating ribbed cotton henley via the fine folks at United By Blue (you might remember that piece as this past week’s Style Pick, in fact). I layered that underneath a brushed flannel workshirt from the new Reef x H.D. Lee Shelter Supply Collection Holiday capsule. You might recognize H.D. Lee as Lee Jeans, and the brand teamed up with noted surfwear retailer Reef on a seven-piece offering that you won’t want to miss if you love American heritage style (and who doesn’t??). Look for more on the workshirt this coming week on the blog, as it was a durable-yet-cozy layering piece that’ll quickly become a winter essential.

A superb burger paired with a nice stainless steel dive watch by Invicta.

And as far as tough style goes, that was definitely in play from location to location. I had the chance to check out the legendary Stella’s, a Grand Rapids icon that serves more whiskey than you can shake a fist at – and oh yeah, their burgers also took home a pretty prestigious prize from GQ in recent years. A stop there for a late dinner Friday night was followed by trips through the tasty Mitten Brewing Company and a stop at Long Road, a great distillery that serves up excellent crafted cocktails (a tip: try The Machine, a coffee-and-vodka combination). To round out the night, we hit up The Winchester, another great bar with an easygoing vibe and plenty of Michigan beer on tap.

After all that, um, activity Friday night, we needed a bit of a pick-me-up on Saturday morning, so clad in my trusty Reef workshirt, we headed to Grand Rapids Brewing Company for an incomparable Bloody Mary bar (can’t beat $4), and a little Saturday college football action featuring our beloved Michigan State Spartans.

I paired the workshirt with my Bonobos Travel Jeans in a fall-appropriate shade of light brown. and the combination worked seamlessly with some new black chukka sneakers, also via Reef. Having the option to take off and add layers while navigating around the city (and namely, from brewery to bar and back) was quite crucial. As to travel style — if you haven’t explored the potential of tossing on a workshirt in place of a jacket, either via Reef or another lower-priced option (like this number from UK clothier ADDICT), I’d advise you do so! Workshirts can be layered over chambray shirts, or worn on their own atop a henley, and the results scream rugged style. When you consider that it can be worn as a jacket or as a true shirt on its own, it’s worth paying a bit more than for your average flannel.

A reverential approach to beer (the brewery is housed in an old funeral home) keeps things classic at Brewery Vivant.

For yet another night out on the town in Grand Rapids on Saturday,  I met up with my best friend Chris, the unfortunate guy who accidentally sat next to me on the bus heading to my first day of kindergarten. So it was awesome to catch up (look for Chris running absurdly fast at your next marathon). The option as to what to do or where to go was pretty easy – being in Beer City U.S.A. makes things rather easy in that regard, so it was excellent to stop into the revered Brewery Vivant. If you want outstanding beer in a beyond-cool environment, I’d recommend you hit up that spot. (Of note: the Farmhand Farmhouse Ale is excellent.).

Stops through a series of Grand Rapids bars followed on Saturday night, including The Meanwhile, an eclectic bar that wouldn’t be out of place in Brooklyn. We also managed to make it for a nice beer at the relaxed Harmony Brewing Company to round out a nice night filled with great times and great friends.

The Urban Institute for Contemporary Arts features a relaxing loft space filled with Herman Miller pieces. It’s the ideal spot to stop and recharge as you explore the city. Slim denim by Mott & Bow. Leather chukka boots by Timberland. Striped socks by American Trench.

Of course, Grand Rapids is about more than beer though – it’s got a bustling arts and culture scene, and if you’re familiar with the massive, citywide art fair and installation that is ArtPrize, you definitely know it’s worth the trip. And the Urban Institute for Contemporary Arts fits right in with the city’s cultural scene. My friend Chris and I had the chance to explore it on Sunday, and the tranquil setting, crisp design and engaging artwork definitely made an impact on me.  The city, of course, also has a nice mix of up-and-established large-scale entertainment entities (like the VanAndel Arena), and it’s on the come-up as they say: construction is booming, new apartment complexes are popping up left-and-right and the city is hanging onto its reputation as being family-friendly. Other outposts like Madcap Coffee, a world-class downtown spot, helped make an afternoon spent exploring the city all the more enjoyable.

Sunglasses by Randolph Engineering. Delicious, creamy Oatmeal Stout by Founders Brewing.

To cap off a whirlwind weekend, we made a stop at yet another revered beer institution, Founders Brewing. The space now features heated outdoor seating, and a relaxed vibe plus some excellent beer was a tremendous way to cap off the trip. The beautiful weather and eclectic mix of new and tried-and-true spots made for an awesome weekend reconnecting with some great friends and exploring a bit more of a city I hadn’t seen in a while. When you travel there, I’d of course recommend bringing some cold-weather travel gear – but more than that, I’d recommend you simply enjoy your time in a city that’s a fine example of the Midwest.

What do you think of these cold-weather style picks? More importantly, have you been to Grand Rapids before, or are you traveling there soon?