Windy City Style: A Summer Weekend in Chicago

Checking out The Bean and Millenium Park on an outstanding summer day in the city. Wearing an American Giant tee and my Need Supply Co. denim jacket, with hair styling courtesy of AXE. Shot by Olivia Hayhoe on an iPhone 7 Plus.

Now, I know what you’re thinking. Wasn’t I just in Chicago? This month even? Yes indeed, Style Guide readers, my travels took me to Chicago for Lollapalooza 2017 just a few short weeks ago and yet … I’m back! Or at least, I was back this past weekend for a family weekend in the Windy City. ¬†My last trip to the city involved a healthy dose of excellent music — including a terrific live show by The Killers — and I was just as excited to be back this time. Incredibly, I’ve even got a fall trip back to Chicago planned, whereby I’ll be sure to pack plenty of fall menswear essentials. Yet, these past few days were about reconnecting with family, exploring the city and catching up with friends right before the end of summer … all in style, of course!

The rest of my family made the trek to take in Chicago’s version of the famed American musical “Hamilton” … while I gave up my seat to my young nephew (Hi, Charlie!), leaving me more time to get out and about in Chicago. That entailed a post-dinner trek to famed indie venue Metro Chicago¬†to see a great indie pop show by Ernest Greene (known by his stage moniker Washed Out). ¬†I’ve gotten quite practiced at loading up my stylish weekender bag with gear to take on the season, from versatile outerwear¬†to a slim chambray shirt and classic sneakers, and this weekend proved no different. Just remember: Going from city to city still calls for on-point travel style. So, let’s get to it.

Men's travel style

Breezy essentials for summer travel, starting with my Grayers Montreaux Windbreaker and carrying through to stylish Frank and Oak leather sneakers and my reliable Huckberry Explorer’s Cap.

Heading straight to the airport in the morning on Friday called for versatile, easygoing style — just as with my last trip to Chicago. Starting with a solid base layer is always key (especially when dealing with airport A/C), so my Grayers Montreaux Windbreaker, a classically designed jacket you might recognize from my Style Pick of the Week series, was the way to go. With its light weight and easy-to-style design, the Montreaux Windbreaker teamed nicely with my equally laidback-yet-polished Mott and Bow denim shirt. Perhaps you recognize the new line of Mott and Bow denim shirts from this site’s Style Pick of the Week series, and I’d say any of the brand’s denim shirts would be a versatile bet the next time you need to throw on a crisp, casual top for travel. ¬†The soft fabric and nicely tailored-but-mobile fit of this slim denim shirt made it an ideal airport layering move, while a new pair of Banana Republic Rapid Movement Chinos¬†offered just the right blend of comfort and stretch.

The whole combo was topped off with my trusty-as-ever Huckberry Explorer’s Cap, a pleasingly vintage-inspired ballcap I love to throw on any time I need to keep the sun off my face. ¬†On the footwear front, a pair of Idyllwild Pull-Up Leather Sneakers from favorite menswear retailer Frank and Oak helped me move around the city with sharp looks and wearbility in mind. And to stay on time, I threw on my trusty Timex x Red Wing Waterbury Chrono, a standout piece from the Timex Waterbury line that looks rugged and goes just about anywhere (particularly with a classic windbreaker and a stylish denim shirt). Want a winning formula for travel style?¬†Pair mobile stretch chinos with leather sneakers and a comfortable shirt featuring textured fabric.¬†

It’s a good thing I was prepped with versatile menswear, because Friday packed in a heck of a lot of exploration and great times around the Windy City. Our accomodations at TheWit Chicago were outstanding — right in the the heart of downtown Chicago, this modern hotel provided a sleek backdrop and stellar views from its roof bar (the ideal spot to knock back a few Bell’s beers — good to be back in the Midwest!). And Friday night’s dinner, featuring family-style pizza, cheese plates and plenty of bread and olive oil, was nothing less than excellent. The next time you get to Chicago, I’d recommend you stop by Quartino!

Mixing earthy tones and casual, versatile staples like an American Giant pima tee and Banana Republic’s Rapid Movement Chinos alongside the CLAE Bradley Mid.

And with Friday in the books, Saturday dawned with the promise of an exciting full day getting to know Chicago more. Seeing as Lollapalooza was packed wall-to-wall with music and I hadn’t visited since college, that left plenty to do — including lots of time spent strolling through MilleniuM Park. As per usual, I prepped with the best men’s gear that I could possibly muster, including a mix of high-low, casual style led by a crisp charcoal pair of my¬†Banana Republic Rapid Movement Chinos.¬†Seriously, if there’s a pair of chinos that combines better range of movement or a more crisp look — the tab closure waist helps with that — I’ve yet to find ’em. ¬†My charcoal chinos matched up nicely with a well-made, breathable Amerian Giant Premium Crew Tee in Drab Olive — a nice contrast of earthy tones that worked well to go from Millenium Park to cool spots like Raised, an urban rooftop spot outfitted with industrial fixtures, premium cocktails and local craft beer.

Saturday’s full ensemble for exploring Millenium Park, highlighted by my CLAE Bradley Mid Sneakers, plus my trusty Need Supply Co. denim jacket and the TImex x Todd Snyder Military Watch.

Like other American-made menswear that I favor, I think you’ll find a simple, stylish T-shirt works with anything on vacation. ¬†The key to a versatile look came from my¬†¬†Need Supply Co. Denim Jacket in 96, another piece that proved a favorite at Lollapalooza 2017 ¬† — it worked just as well this time around, especially as a shot of color to contrast my rich Cocoa Leather Bradley Mid Sneakers from CLAE. This style is comfortable and durable, and for this late August trip, that made them a prime footwear pick. That comfort definitely helped me get around in style — my MVMT Watches Runaway Aviators also helped shield my eyes from the hot Chicago sun, and we took the chance to keep the afternoon rolling. The Chicago Athletic Association Hotel, completely refurbished and recently reopened, harkens back to the city’s glamour and refinement of years gone by. It comes complete with a rotating pop-up bar on the ground floor, plus a game room and ¬†a neat rooftop bar with great lakefront views.

A stylish weekender bag, American Giant shorts and a breezy chambray shirt made for easy travel style.

But as always seems to be the case, the weekend drew to a close too quickly. I had just enough time for a delicious Sunday brunch at the uniquely ’70s-inspied HopCat Chicago lounge before departing the Windy City yet again — and I dressed in casual, breezy travel style to take on the day. For a bit of tailored style mixed with supreme comfort, my all-new American Giant Weekend Shorts — made from hefty rugby jersey cotton — were perfect for a flight back to NYC. And to mix in some high-low style, I threw on my trusty United By Blue Wenlock Chambray Shirt.¬†What with breathable fabric and a neat pattern, the Wenlock Chambray Shirt added some contrast to my laidback CLAE Hayward Sneakers, at once retro and yet crisply modern. And on the accessories front, a handy travel kit and men’s grooming essentials from Baxter of California¬†paired up perfectly together, while my rugged-yet-accessible Timex Waterbury Chrono Diver helped me stay on time in casual style. In all, the laidback, breezy style ensemble helped me make it back to NYC in good time and in good style.

I hope you spent your weekend in the same way I did — with great friends and family, enjoying great times. You can ¬†be sure I’m already looking forward to my next trip — to Chicago or elsewhere. To keep up with my travels and my style tips, check out my Instagram. And tomorrow, you can join us for another #OOTD. Until then, stay stylish!

-Beau

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Style Pick of the Week: Danner x New Balance miUSA 585 Sneakers

Editor’s note: Expect these posts weekly detailing one standout item coveted by yours truly. Sometimes, these fit within budgetary restrictions and other times, they’re expensive splurges worth saving for. For more Wish List items from Beau, head here, and to see other Style Picks, head here.

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Contemplating the weekend in NYC’s Bryant Park — during a Friday lunch break. miUSA 585 Sneakers from the Danner x New Balance collab. Cole Bomber Jacket by Beckett Simonon. Cove Shirt by Life/After/Denim. Slim black selvedge by Todd Shelton. Waterbury Chrono by Timex x Red Wing Heritage. Colorblocked socks by Richer Poorer. Glasses by Frameri.

Perhaps it’s been the slightly breezy, fall-esque weather in Brooklyn, but durable, premium footwear is certainly something that’s been on the mind of your Style Guide¬†publisher, editor and writer as¬†of late. Although we just covered the excellent SeaVees Huckberry Chukka in last week’s Style Pick of the Week post, we’re back at it here with a pair of footwear that’s every bit as perfect for fall style — and quite a bit pricier, if we’re being honest.¬† Yes indeed, the Danner x New Balance miUSA 585 is quite the sneaker, blending the ingenuity and technology of New Balance with the quality and craftsmanship of Danner. Oh, and it’s made in America at New Balance’s Maine factory. Sounds too good to be true, ehh? Not so fast, my friend. Having tested out these sneakers, I can tell you that they’re the real deal — and then some.¬†The Danner x New Balance miUSA¬†585 takes advantage of the best of the best that these two Portland-based companies have to offer (that would be New Balance’s roots in Maine, and Danner’s home base in Oregon). It’s part of the American Pioneer Project, and¬†that partnership also features the Danner x New Balance Light, an outdoor boot that merges hybrid style and performance. The 585 is a bit of a different look from your classic boot or sneaker, though. The 585¬†takes New Balance’s traditional¬†outdoor trail silhouette, and merges it with the sort of durable touches found on Danner boots, like rich Horween leather. Boot laces give these sneakers a¬†sporty-yet-versatile look, and ballistic nylon found on the upper also gives it a ton of durability, as does¬†So is it a sneaker? A boot? How do you wear it? All crucial questions given the price tag ($359.99 ain’t exactly cheap, fellas).

The answer to the first of those two questions would be that, yes — it’s a sneaker. But it can wear like a boot. The higher heel prevents you from rolling your ankle, critical whether you’re dashing to the subway or the plane — or stepping out of your favorite pub (right? Right??). It’s fit for casual Friday pairings aplenty, as you can see above — try it with a beautiful Beckett Simonon suede bomber jacket, a patterned shirt (the one at the top is from Life/After/Denim), and slim black Todd Shelton selvedge. Now, you’ll have to wait for that bomber jacket, but the good news is that you can pick up these sneakers, and wear them, right away. The rich Horween leather gives the Danner x New Balance miUSA 585 a dressier feel than most¬†kicks¬†— given the price tag, you’re going to want to get as much wear out of them as you can. Just be sure to keep them nice and cleaned up (soap and water¬†on¬†a¬†cloth is a¬†quick way to keep the heel and sole scuff-free).¬†The Horween leather¬†should develop a¬†nice patina over time, too. And lest¬†we forget, the¬†combination between sporty and casual style means you can team them up with a lightweight navy blazer and¬†dark blue¬†denim¬†at the office, and they’re absolutely perfect to wear with a slim cardigan and a¬†classic Taylor Stitch chambray shirt¬†for a sharp weekend coffee run. The difficult thing is going to be resisting the urge to wear them into winter — these are sneakers that should be stored for a¬† bit, then broken back out in the spring. In the meantime, the Danner x New Balance miUSA 585 will look plenty handsome on your shelf.

While you mull that sneaker purchase, follow along with The Style Guide on Facebook.

Style Pick of the Week: Buck Mason Short-Sleeve Chambray Shirt

Editor’s note: Expect these posts weekly detailing one standout item coveted by yours truly. Sometimes, these fit within budgetary restrictions and other times, they’re expensive splurges worth saving for. For more Wish List items from Beau, head here, and to see other Style Picks, head here.

Savor the last weeks of summer with a chambray shirt that can tackle anything. Flowing locks and well-kept beard not included.

Savor the last weeks of summer with a chambray shirt that can tackle anything. Flowing locks and well-kept beard not included. Photo courtesy of Buck Mason

So you’ve got your slim chinos¬†and your classic white sneakers, but you don’t quite have a shirt to wear with ’em — or do you? The Buck Mason Short-Sleeve Chambray Shirt, my friends, is that shirt — and if that’s not the one,¬†I’d suggest the Buck Mason Oxford. But as to the Short-Sleeve Chambray Shirt: It fits in quite well with the brand’s line of durable, essential basics, which run the course from crisp blue denim to perfectly washed slub tees. And it fits in very well with the sort of menswear you should be looking to rock to finish out summer. We’re talking pieces that can handle a beach walk or a day by the pool, and then drinks out on the¬†town. And we’re talking just as much about pieces that can be fun to wear. If¬†you’re¬†on the hunt¬†for a unique alternative to a classic summer polo or a slim pocket T-shirt, the short-sleeve chambray shirt is the way to¬†go — as¬† a matter of fact, you can rock the style at least five different ways (wink, wink). The light wash is casual, the workwear-inspired front pockets are a nice visual touch, and the styling potential is certainly tough to beat.¬†Yes indeed, the Buck Mason Short-Sleeve Chambray Shirt¬†can be worn with everything from a pair of stylish swim trunks and¬†slip-on sneakers on Saturday¬†to linen trousers on a casual Friday — no jacket required.¬†And with Buck Mason, you’re getting every bit you pay for — and then some.

Subtle details like front-button chest pockets switch things up from the standard navy polo.

Subtle details like front-button chest pockets and fish eye buttons switch things up from the standard navy polo.

The brand’s story began with a conscious decision to¬†return to American manufacturing, and that commitment to quality and effortless style shines through here. While “heritage style” can sometimes have negative connotations (as seemed to be the case after the trend blew up in the mid-2000s), there’s nothing overly costume-y or dated about a very well-fitting, very well-made short-sleeve chambray shirt. Critically, this shirt¬†is made with a lightweight indigo-dyed chambray — that means it’s breathable and moves easier than heavier shirts cut for fall or winter. Another big benefit? It’s made in America, so it’s right in your wheelhouse if you like to know where your #menswear comes from. And although this particular Buck Mason chambray shirt has short sleeves, know that you can still¬†team it up with, say, a lightweight cotton sweater¬†after a day on the water —¬†it’s even better for layering in that regard.¬†But the benefits don’t stop there — it’s got a bit of an edge to it, to the point where it wouldn’t look out of place worn with¬†an iconic jean like¬†the Levi’s 505C at a rock concert.¬†The tricky part is going to be keeping¬†this shirt¬†in your closet once fall and winter really hit — so if you’re blessed enough to live near Buck Mason’s Los Angeles home base, do us all a favor and continue to rock it year-round.

Click here to get the Buck Mason Short-Sleeve Chambray Shirt.

Do you own any Buck Mason gear? How would you style this chambray shirt? Weigh in at The Style Guide!

Style Pick of the Week: American Trench Cotton Rugby Stripe Socks

Editor’s note: Expect these posts weekly detailing one standout item coveted by yours truly. Sometimes, these fit within budgetary restrictions and other times, they’re expensive splurges worth saving for. For more Wish List items from Beau, head here, and to see other Style Picks, head here.

Pick one or pick 'em all -- just one of several solid sock options from American Trench.

Pick one or pick ’em all — just one of several solid sock options from American Trench.

The photo and title of this post isn’t a mistake, trust me. We’re just talking about socks, right? Indeed. A great pair of socks is indispensable no matter the time of year, be they a no-show pair for the warm days of summer or something a little thicker — like these Cotton Rugby Stripe Socks from American Trench. You might recognize the brand from a past entry as part of this site’s Style Q&A series, and if you haven’t paid attention to date, it’s best time you start. The brand is all about crisp, clean, understated designs, something that sets them apart from other sockmakers who favor bolder, louder patterns. A pop of color or a great pattern is definitely to be commended, and those are the types of socks I wear myself¬†more often than not¬†¬†— yet when a knitwear company lets the fabrics and materials speak moreso than the pattern, that’s when you take notice. American Trench manufactures its socks at family-owned mills in North Carolina and Pennsylvania, and does so in small quantities — so you definitely get what you pay for. And at $44 for a 4-pack of the socks pictured above, that’s a very good thing.

The medium weight and striped pattern make these socks a great pair to ground complementary colors. Sky-blue chinos by Combatant Gentleman. Waterproof chukka boots by Timberland.

The medium weight and striped pattern make these socks a great pair to ground complementary colors. Sky-blue chinos by Combatant Gentleman. Waterproof chukka boots by Timberland.

That’s one thing to note¬†about the brand’s socks overall — they are indeed pricey compared to your average pair. But you get the choice of some intriguing fabric blends — pima cotton¬†and superfine merino are but two picks — plus a nice swath of colors fit to pair with everything from inky blue denim to grey chinos. And as you can see above, the brand’s Triple Stripe sock offers a solid complement to some sky-blue chinos, too. After testing out some pairs through this fall, these socks are every bit as good as advertised — and priced. They’re comfortable, breathable and stylish. There are small points of reinforcement (or what feels like thicker fabric) at heavier wear areas, and they don’t slide down your calves throughout the day thanks to a spandex-lycra blend.¬†The option to select from some neat designs, like a zany-yet-reserved Fair Isle pattern, is another bonus. The pairs I’ve tried out — including those Fair Isle socks — fit comfortably in some sturdy boots, and they also fit in just fine with a nice pair of leather sneakers. Add all this onto the fact that they’re durable, comfortable and made in America, and you might not want to buy from another sock brand this fall — or any other season.

Do you own any socks from American Trench? How do you like your socks — wild and wacky, or more reserved?

Ben Sherman US