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.

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