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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See Now, Buy Now: Add to Your Watch Collection with the Timex Waterbury Stainless Steel Dive Watch

Timex Waterbury

One heck of a watch for the price — maybe one to buy right now, as it were?

One of the things that comes up a lot at The Style Guide (weekly? daily?) is the importance of buying quality, affordable and versatile #menswear pieces. From a classic Oxford shirt to a rugged henley to slim, American-made denim, that type of quality and wearability is out there — if only you know where to look. Such is the case with Timex, a brand that you might have glazed over in the past, one that now deserves a second, or third, look. And in the latest entry in our ongoing See Now, Buy Now series, we’re giving the rugged, essential Timex Waterbury Stainless Steel Dive Watch a close look — it’s among the best men’s casual watches to buy now, I can say that much.  The Waterbury Stainless Steel Diver plays off the brand’s vintage-leaning, stylish Waterbury line — surely, you’ll recognize the rugged Timex x Red Wing Waterbury Chrono from the pages of this blog. The Waterbury Stainless Steel Diver is in a league of its own, starting with the standout price and carrying right on through to its handsome, subtly stylish and easily wearable aesthetic.

It’s a rugged men’s dive watch that gets the look right without a cluttered design. While it’s not exactly made for plunging into great depths in the ocean, it’s a daily watch that’s more than serviceable thanks to the classic durability for which Timex is known. For you and me both, that’s great news. And the better news? You can get it via Bespoke Post, purveyors of plenty more of your favorite #menswear.  If there’s one watch to wear to the office with a classic navy blazer during the week while also teaming it with a rugged short-sleeve henley on the weekend, it’s the Waterbury Stainless Steel Diver. Folks, that type of affordable style can’t be emphasized enough. And a rugged stainless steel dive watch is the perfect piece to add a bit of toughness and visual interest to cold-weather outfits, too — perfect given that we’ll be into fall before you know it. With all that being said … I can’t recommend the Waterbury Stainless Steel Diver enough. That’s as true right now as it’ll be when fall hits.

Shop away, and thanks for reading!

-Beau

#OOTD: How to Dress for Summer Travel

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 series will take one great item and put together a versatile, stylish outfit around it. Look for past features here.

One of the biggest steps in improving your style — whether you’re new to this whole #menswear game or digging in deeper — is making that extra effort to look great even when you’re off the clock. That could mean one of many possible situations, like dressing for Sunday brunch or prepping for a spring bar crawl, but given where we are on the calendar, it likely means you’re wondering how to dress for summer travel. It’s a curious task that can be a tall order — looking your best while on the road means dressing sharply, staying comfortable and finishing off your kit with excellent accessories, like one of the best dopp kits for men (written by yours truly, as it were). The below #OOTD incorporates a bit of everything, including chinos fit for travel — an upgrade over the sweats that some might be wearing — and a navy blue blazer that can go anywhere and do anything. Add in accessories fit for your everyday carry as well as a long day on the road, and you should be set. Got questions or comments? Hit me up on The Style Guide Facebook page. To see what I’m taking as I travel, follow me on Instagram — and we’ll see you on the open road!

Taking a traditional travel outfit and upgrading it with slim fits and go-anywhere essentials.

Taking a traditional travel outfit and upgrading it with slim fits and go-anywhere essentials.

The Chinos: Apolis Civilian Travel Chino, $138: A staple of any great outfit, these cotton chinos should be comfortable for flying and look a heck of a lot better than what your seatmate might be wearing (it’s all in the name, right?). Plus, they can go from the plane to a meeting to dinner — or just from the plane to a bar, your call.

The Shirt: Bourbon and Blue Beachcomber Shirt in Blue Chambray, $89: Here’s an easy style hack — stay cool yet look sharp by ditching the sleeves of your classic chambray shirt in favor of something cut slimmer and sharper. The Shoreline Check fabric from this upstart brand should add nice visual interest, too.

The Jacket: Grayers Cayman Blazer in Navy, $175: A knit blazer that ditches the traditional trappings of a jacket — AKA, no construction here to speak of — should fit sharply and stylishly over that crisp chambray shirt.

The Shoes: Soul36 The Grant Derby in Brown Nubuck, $195: A new take on the derby shoe, these brown nubuck shoes are made with a clean look in mind; the red-brick sole should offer a refined bit of contrast beneath the grey chinos.

The Socks: American Trench Summer Footies, $13.50: Because you’re going to want a nice, clean finishing touch beneath those rolled chinos, reach for durable, comfortable, American-made socks.

The Belt: J. Crew Classic Buckle Belt, $45: Sometimes, you don’t need an overly fancy belt — just a reliable classic that goes with your best business-casual or your best summer wedding look.

The Watch: Timex The Waterbury, $95: Part of Timex’s revamped line of heritage-inspired classics, the Waterbury is a reliable watch that’ll pair just fine with this outfit — or with a polo and chinos later on.

The Travel Companion: Jack + Mulligan Passport Wallet in Brown, $74.99: If you’re jetting overseas, this piece could be especially useful and stylish. But even if you’re only hopping on a train an hour or two away, this piece could still work reliably well when it comes to carrying a notebook.

As with many style upgrades, dressing for travel comes down to assessing what you’ve got, then pairing it up in ways customized to the situation. So a short-sleeve chambray shirt and a knit blazer are going to be lightweight, comfortable and reliably stylish options whether traveling for business or pleasure. And some eye-catching brown nubuck shoes cap off the outfit o in a way that works for multiple situations. Plus, a dependable Timex watch can go just about anywhere, as can comfortable no-show socks. If it gets hot out, ditch the blazer — and if you still need it as the trip goes on, be sure to store it in a stylish weekender bag. If you’ve got questions on how to dress for summer travel, hit me up on Twitter. Check back tomorrow for a neat reader giveaway opportunity that might just help you when you hit the road next time.

Stay stylish!

-Beau
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