Taking in Lollapalooza with my MVMT Watches Aviators, plus my rock-ready Need Supply Co. denim jacket and slim Abercrombie and Fitch denim — finished off with classic Astorflex suede chukkas.

It was under special circumstances that I hopped on an unusual Thursday night plane ride out of NYC to head to Chicago — and no, I didn’t take a wrong turn after happy hour. I hit the road last weekend to head to Lollapalooza 2017 in the Windy City — a truly momentous weekend packed full of highlights, from great #menswear to an amazing Friday headlining set by The Killers (a band I’d seen back in June) and more excellent tunes than you could take in across just two days. It was my second festival in as many weekends after attending the Panorama music festival here in NYC — with Governors Ball 2017 also under my belt this summer, you night say I’ve got it down to a science when it comes to what to wear to a music festival. What exactly did I pack and who did I see? Join me on another men’s travel style post — it should come as no surprise it was an amazing weekend that seamlessly blended my two big passions! Put on your favorite Killers track, and let’s rock.

I packed up my Owen and Fred Voyager Waxed Weekender with trusty essentials, from my Astorflex suede chukka boots to my Huckberry Explorer’s Cap.

The adventure itself really began on Thursday night, as I packed up my stylish weekender bag — namely, the Owen and Fred Voyager Waxed Weekender — with menswear essentials galore. To head from a full day at the office to the airport, I dressed in a mixture of comfort and style, starting with a new pair of Abercrombie and Fitch denim from the brand’s recently revamped line. The mobility, tailored fit and pleasingly faded wash matched nicely with one of my favorite Taylor Stitch shirts, the Sashiko Shirt — the cool detailing and texture makes it a four-season essential, and it’s yet another example of what Taylor Stitch does well. The combo was finished off with even more comfort in the form of my travel-ready Astorflex suede chukkas. There might not be a more versatile pair of three-season shoes than these classic suede chukkas, which can go from the office to the plane easily.

A stylish casual watch from Nautica and my reliable Huckberry Explorer’s Cap rounded out my travel style essentials. And the next time you hit the road, don’t forget to pack men’s grooming essentials — a few pieces from the Oars + Alps Athlete’s Grooming Kit (as seen on this site’s Style Pick of the Week series) helped me keep my skin in top form. What’s more, I even managed to prep for the festival on the music front — I plugged in my surprisingly stylish LSTN Sound Co. headphones from the essential Bespoke Post Vibes Box, and I was ready to go. The bottom line is this: When dealing with a day at work and an evening of travel, dress for comfort, style and mobility (like I did!).

Easygoing essentials for a day of music and a day in the sun — particularly a fan of my classic SeaVees Army Issue Sneakers, and they teamed nicely with my tough, versatile Timex x Todd Snyder Military Watch.

My Thursday night arrival had me tired but wired (tired and wired?) going into an amazing, bright and sunny Friday full of live music. To take on Chicago’s heat, I kept things simple and stylish with a slim short-sleeve shirt from Old Navy, plus my laidback and comfortable Bridge and Burn Stringer Dune Shorts — two warm-weather style essentials fit for any trip.  And just as with Panorma, I found my SeaVees sneakers to be effective, comfortable and broken-in enough to fill that crucial music festival style void. And that blend of style comfort from my SeaVees sneakers proved quite effective for bouncing around Lollapalooza’s many, many stages. That meant staying on time was quite critical — as I’ve found on many a music-themed trip, my Timex x Todd Snyder Military Watch on a cotton NATO strap (similar style here) was a durable and stylish pick. I topped it all off with stylish men’s sunglasses — namely, a new favorite pair of sunglasses from Component out of Miami. And what exactly did the day have in store? Plenty — to say the least.

There aren’t many festivals where you’ve got the chance to see everyone from Brooklyn indie rockers Slothrust to classic modern indie pop duo Tegan and Sara to upstart British singer Bishop Briggs within a matter of hours, but Lollapalooza absolutely delivered in that regard — I  can’t say enough about the experience. A vibe-filled, sharp set from Phantogram paved the way for an exciting, anticipation-filled evening — a long-awaited show by The Killers tends to heighten the excitement of a music festival even moreso. Having just seen this remarkable band back in June, I thought I was ready — yet nothing can really compare to the power, energy and joy brought to the stage by Mr. Brandon Flowers and company. I’ve said it before and I’ll say it again: There’s really nothing that can measure up to seeing songs you’ve known for half your life being played out in person. When delivered by one of my heroes, Brandon Flowers, it was all the more special. (Editor’s note: Mr. Flowers inspired my love for denim jackets and black moto jackets, surely). 

From classic cuts like “Mr. Brightside,” “Read My Mind” and the roaring “For Reasons Unknown” to all-new cuts “The Man” and fan favorites like “When You Were Young,” this is a band that delivers on nearly everything that a fan could ask for. That included a soaring cover of fellow rockers Muse, plus a menacing (and yet wonderful) cover of the Joy Division classic “Shadowplay.” This is, simply put, an incredible band. I mean that sincerely, and it’s nothing short of an absolute joy to witness live. And as it were, I positively can’t wait for The Killers North American tour behind the band’s forthcoming new album, “Wonderful Wonderful” — what a run that should be. It was worth the trip in and of itself, and that’s no joke. Incredibly, I wasn’t quite fully tired out from Friday night — and Saturday promised even more tunes and even more #menswear.

Crisp and effective, rock-n-roll style featuring slim Abercrombie and Fitch Langdon denim and my classic Astorflex suede chukkas.

Although Saturday dawned hot and sunny once again, I went with sharp and simple style — perhaps inspired in part by the style of Brandon Flowers, who frequently favors all-black get-ups. For me, that meant injecting some color and texture on the footwear front with my Astorflex suede chukkas and topping it off with another pair of slim Abercrombie and Fitch Langdon denim in a slightly faded black wash. Perfect for a festival — particularly when teamed with my Knickerbocker Mfg. Co. Pocke Tube Tee. For taking on the day and seeing the vibe-filled, standout rock of The xx later, an all-black uniform certainly felt right — my trusty Timex for J. Crew field watch helped add some texture and visual interest to the look, too.  Once again, I just had to get ready for the day with the stylish and high-quality LSTN Sound Co. headphones from my Bespoke Post Vibes Box.

Saturday itself brought out a terrific mix of live acts, too. Canadian rockers Alvvays — a band that’s been on my list for more than two years now — brought a shimmery, sunny mix of indie rock to the Bud Light Stage in the afternoon. Later in the evening, personal favorites The Head and the Heart delivered just as rousing a performance as they did at Govenors Ball 2017 and on a winter road trip I took to Baltimore to see them play.  And throughout the day, Lollapalooza delivered just as solid of a mix of artists as one might expect — from L.A. rockers Warpaint to the joyous dance grooves of pop duo Sylvan Esso and the unique rhythm and quirky vibes of British rockers alt-J (another favorite of mine). The experience and atmosphere was truly jam-packed and lively — it was as busy a two days as I’ve had at a music festival, particularly navigating multiple stages and trying to stay on time. Again, dressing for a music festival in style proved absolutely critical, and I hope my gear was up to the test. As it were, my all-black get-up fit right in during a powerful, transcendent Saturday night headlining set by British rockers The xx —  another personal favorite and another band that made the entire trip worth it.

Travel-ready gear for the flight back — my Need Supply Co. denim jacket and my new Bridge and Burn Basic Tee got the job done on my top half, while my Kit Culture stretch twill pants were suitably travel-ready.

All too soon, it was time to hit the road back to Chicago — my schedule precluded me from staying another day to take in the powerful rock and spectacular live show that is Arcade Fire, but I left Chicago with nothing but happy memories from an incredible weekend of amazing music. And with a stylish weekender bag and men’s grooming essentials from Oars + Alps in tow, I made sure to dress for the road accordingly. I started out once again with my versatile Astorflex suede chukkas  — they’re as comfortable and sustainable a pair of classic chukka boots as you’ll find. They were a sharp complement to my Kit Culture stretch twill pants, a tailored set of chinos that feels like an easy-to-wear pair of sweatpants. When topped off with my Need Supply Co. Denim Jacket in 96 — a retro-inspired, versatile denim jacket — I was more than ready to deal with blasting airport air conditioning. Between the light wash and the quality construction, the denim jacket was a cool topper to a new Bridge and Burn Basic Tee — think an ultra-soft blended T-shirt built with made-in-America craftsmanship. The next time you hit the road, reach for breezy basics, a well-made denim jacket and go-anywhere pieces like suede chukkas. 

With all that travel in the books, I was glad to make it home last night — and it was all the better to get back to Brooklyn knowing I’d had such an amazing, fulfilling trip. Hopping on a flight to a music festival can feel like a long journey at times, but the trip was more than worth it — heck, seeing some of my heroes on the stage on Friday night made the trip in and of itself. I’m also lucky I was able to pack up just the right gear for the weekend — if I can continue to make the trip in years to come, I’ll be looking at a longer trek than just a subway ride … and I know it’ll certainly pay off.

Did you manage to make the trek to Lollapalooza? What did you bring along with you? 

Lastly — thanks for reading!

-Beau