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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Online Shopping Picks: The Best Men’s Transitional Footwear for Spring

Join us for the ride today as we kick off another Online Shopping Picks entry¬† — if you’re looking for the best men’s transitional footwear for spring, you’re in luck.¬†¬† What exactly do we mean when we say transitional? Well, we — and by we, I mean me — aren’t exactly talking about rugged winter boots or even classic summer sneakers. No, today we’re talking footwear that’s a touch more durable than your average set of kicks — maybe they combine a¬†few different elements, like the cut of a chukka and the materials of a sneaker (see: Exhibit A, the SeaVees Huckberry Chukka).¬† Or maybe, they’re both slightly dressy and yet suited for casual wear. Better yet, they should be relatively durable and versatile for fighting spring rain and looking great at the same time. So, you’ll see a solid mix below, from sleek suede chukkas to durable sneaker-boots and everything in between. If you agree with these picks — and even if you don’t — join me over on The Style Guide Facebook page to pick up what should be a lively #menswear discussion.

Greats

#1. Beckett Simonon Laval Suede Chukka Boots in Chestnut — $199

Supremely stylish and water-resistant suede chukka boots — perfect.

I’ve been fortunate enough to test out some Beckett Simonon¬†footwear across the past few months, namely during a fall weekend in New York City. And the good news is that the brand’s chukkas are sturdy, sleek and extremely stylish. Such is the case with the Laval Suede Chukka Boot in a handsome shade of Chestnut. Pre-order these now and wait for them to arrive, because I’d wager you’ll want to wear them with everything from slim light wash denim to chinos. Oh, and an even better perk? The water-resistant suede, fit for taking on inclement weather.

#2. SeaVees Mariner Boot in Navy or Olive — $149.98

SeaVees

A collaboration between SeaVees and Taylor Stitch, with very stylish results.

When it comes to talking transitional footwear, the¬†Mariner Boot¬†just might be the ideal pair to buy now — and wear very frequently when spring rains roll through.¬† The end result of a collaboration between our pals at SeaVees and Taylor Stitch,¬†the Mariner Boot features a British Ventile waterproof duck canvas upper for crucial spring protection. Plus, SeaVees’ signature herringbone tread outsole adds a nice dash of traction on wet streets, and the option to pick up either the Navy Mariner Boot or the¬†Olive option bodes well for those of us who appreciate versatile footwear.
Frank & Oak

#3. AstorFlex Bitflex Chelsea Boot in Dark Khaki — $180

Astorflex Chelsea Boots

The combination of suede and a Chelsea boot silhouette is especially crisp for spring.

As seen in a Style Pick of the Week entry last fall, the Astorflex Bitflex Chelsea Boot¬†has a lot going for it — it’s stylish and sustainably made, for one. And crucially, it combines both a relatively slim profile and a unique crepe rubber sole. Plus, who doesn’t love a great Chelsea boot? It’s an of-the-moment silhouette that’s transcended, well, trends, to become a footwear essential. And if you haven’t tried out a pair, this spring might be a good time to start. While they’re not water-resistant like the Beckett Simonon suede chukkas above, you still get nice quality & sharp looks.

#4.¬† CLAE Hayward in Mojave Pig Suede — $100

Retro style meets functionality — waterproof suede and a neat silhouette.

The retro-style runner continues to have a moment in the menswear space — in other words, it’s simply an excellent-looking shoe style. If you love a great pair of sneakers, give the CLAE Hayward a look if you’re seeking a¬†new way to shake up your spring footwear rotation.¬† They’re certainly unique in both looks and functionality, incorporating waterproof suede with nylon side panels atop a crisp runner’s sole. Wear these guys with white jeans and a slim short-sleeve chambray shirt — plus a¬† stylish denim jacket — on a breezy spring day, and you’re all set.

#5. OluKai Pahoa Boots in Black Seal/Brown — $200

Note the burnished leather, waxed laces and easily wearable design.

If you’re sensing a theme in this post — that of durable footwear that also looks sharp — then you’re right on the money. And the last entry on the list definitely falls underneath that umbrella. Comin’ at ya all the way from Hawaii, the OluKai Pahoa Boots feature some mixed-media design touches — note the contrasting upper and waxed cotton laces. What’s more, the footbed features EquilFit technology for comfort and performance. Not bad for a pair of¬†leather chukka boots, ehh?

Honorable Mention: Thursday Boots Honey Suede Scout Chukka — $149

Crisp, clean and well-made — all for under $150. That’s what you get with Thursday Boots.

We’re bringing back the Honorable Mention category in these Online Shopping Picks posts, namely because it’s mighty tough to pick just five great pairs of stylish spring footwear. And when the final brand on the cut line is Thursday Boots,¬†you can be darn sure we’ll give ’em a second look. Featuring a slick European-inspired silhouette and plenty of traction via a studded rubber outsole, these are dressy enough for the office and more than ready for Sunday brunch.

From start to finish, I hope you enjoyed this essential, excellent, even tremendous rundown of the best men’s transitional footwear for spring. Finding shoes that serve a purpose while providing comfort and functionality can sometimes be tricky — yet, plenty of brands are hitting that sweet spot quite nicely.¬† From the water-resistant suede of the Laval Suede Chukka Boot¬†to the toughness and on-point styling potential of the Mariner Boot, you’ve surely got options aplenty. If retro-inspired style is more your bag, grab the CLAE Hayward for a change, and I’d urge you not to pass up¬†a pair of dressy-yet-versatile Chelsea boots (like the Astorflex Bitflex Chelsea Boot). Of course, who can resist yet another pair of suede chukkas, like the Thursday Boots Suede Scout Chukka? No one, that’s who.¬† If you’ve got questions on how to style these boots or heck, if you should buy any of them, drop me a line via Twitter or in the comments below.

More importantly — stay stylish!

-Beau