Hanging out at TwentySix Cafe in versatile, rugged gear for exploring Portland. My Bridge & Burn Northfork Woodland Jacket, the Taylor Stitch Sashiko Shirt, All-American Washed Jeans from Flint and Tinder and my Grizzly Wheat President Boots from Thursday Boots worked out tremendously!

Before we kick things off in today’s latest travel style feature on The Style Guide, know that we’re not about to dive into a “Portlandia” parody (as outstanding as that show happens to be). No sir, this past weekend gave me the chance to head West — although I’d spent a weekend exploring Los Angeles and even made a trip out to Las Vegas for work last year, I’d never been to the City of Roses. I’ve been hearing great things about its balance of excellent #menswear, standout craft beer, a great culinary scene and of course, stellar live music — in my book, that’s more than enough reason to get out and adventure.

And the my long weekend brought with it the added value of an amazing concert — always a bonus! Yes indeed, seeing excellent synth pop band Future Islands play the renowned Crystal Ballroom was a heck of a treat on Friday night. Although it was quite the long trek to get out there following a long work week in New York, I did my best to pack in style (as you might have seen via my Instagram page). Come along for the journey!

Slim, faded denim, a durable Saddleback duffel bag, trusty James Dean Eyewear sunglasses … all that you need for a weekend out West.

Traveling in style and comfort can be a bit of a challenge — particularly on a long flight. That’s why I reached for my durable, pleasingly faded All-American Washed Jeans from Flint and Tinder. Made from premium cotton denim and finished with just a hint of stretch, my All-American Washed Jeans were a fine pair of denim to go from the airport to go to the hip, quiet and cozy TwentySix Cafe near my Irvington accommodations. And my uniquely detailed Taylor Stitch Sashiko Shirt worked just as well on the plane as it did trekking around Portland, particularly when teamed with the richly crafted Grizzly Wheat President Boot from Thursday Boots. To stay on time through it all, I reached for a brand-new, slim and refined Timex watch — the versatile leather strap proved easily wearable all day long. To shield my eyes from the sun in style, a new pair of James Dean Eyewear JDS100 Sunglasses looked great and proved up to the task. The next time your trip calls for exploring a new city on foot, reach for mobile denim, comfortable-yet-tough boots, a sharp watch and stylish, go-anywhere shirting. 

All the right details for exploring Portland, including a new Timex watch and my rugged Thursday Boots Grizzly Wheat President Boots.

And exploration was certainly the name of the game on Friday leading up to that night’s Future Islands show. Thankfully, my durable, rugged and extremely well-crafted Saddleback Rounded Leather Duffel Bag held up to the challenge of lugging around my favorite travel style essentials as I hopped from grabbing a crucial cold brew to the excellent Bunk Bar Wonder, one of a series of PDX locations offering gourmet sandwiches, excellent craft cocktails and a very solid beer selection. A hint — get the Molě Tator Tots, packed with delicious flavor. It was a great afternoon lead-in to a stop at the richly appointed Tanner Goods Flagship Store and the accompanying craft cocktail/beer bar & patio, The Wayback. This American-made brand has long been a favorite of mine for handsome leather goods, durable outerwear, stylish home decor and terrific attention to detail — it was a treat to finally stop by! So with coffee, menswear and craft beer on lock, that led to the night’s highlight: Future Islands bringing down a packed Crystal Ballroom with a stellar show! It helped that I dressed in comfort and style; I can simply never resist the chance to wear rugged leather boots to a concert, either.

The Baltimore-based synth pop band’s rise to fame has been a long one — they’ve played more than 1,000 shows across the country since 2006, often booking them on their own. And if you’re not familiar, I’d say you’ll recognize them from their 2014 appearance on Letterman playing hit single “Seasons (Waiting on You).” Believe me, frontman Sam Herring is every bit as energetic, passionate and enjoyable in person — I knew that from seeing the band play Panorama 2017 here in NYC! And their return to Portland was an anticipated one, coming as it did off the release of one of this year’s better albums, the emotionally packed “The Far Field.”

With an extensive discography spanning five albums and plenty of crowd favorites, a Future Islands show is full of highs and lows, joy and passion — it’s a sight to behold, from hits like 2017’s “Ran” and 2014’s “A Dream of You and Me” to fan favorites like “Seasons,” of course! And Crystal Ballroom, what with a historic interior and a tremendous craft beer selection — including choice selections brewed in Portland — is simply a quirky, cool, standout venue for a live show. Did it top my trip to Nashville to see Young the Giant and Cold War Kids? It’s tough to say – but Future Islands blew me away yet again. Even dealing with a bit of jet lag, it was still a heck of a way to cap off a big Portland day.

Durable Allen Edmonds boots, a finely crafted Abercrombie cotton shirt and a durable Timex x Red Wing watch — perfect Portland essentials.

So, with Friday night in the books, my Saturday kicked off in style — from the ground up, as it were. For getting around Portland with durability, rugged looks and sharp versatility in mind, my brand-new Allen Edmonds Caen Cap Toe Boots worked extremely well. Of course, I started my day right on time with my Timex x Red Wing Waterbury Watch, but stellar boots were just as critical. Coming from a brand mainly known for stylish men’s dress shoes, these rugged cap toe boots are a welcome addition to the Allen Edmonds line — and what’s more, they worked nicely in tandem with the crisp, easily wearable Flint and Tinder 365 Pants. Cut like a five-pocket pant and made from a blend of cotton and lyrca, my 365 Pants helped me grab a quick coffee at essential Portland stop Blue Star Donuts before kicking off afternoon shopping at Style Guide favorites Bridge & Burn. On the shirting front, I reached for a nice fall go-between — a new Abercrombie & Fitch Herringbone Shirt, courtesy of the brand. I can’t recommend the rugged versatility of Abercrombie & Fitch enough, and this soft-washed cotton shirt was able to withstand a full day out and about in Portland.

I packed a lot into an already busy day, including a stop at the excellent Kiriko Made shop — renowned for indigo textiles, excellent shirting and stunning attention to detail on items as small as pocket squares, Kiriko should certainly be on your shopping list if you get out to Portland.  And just as with my trip to Nashville, I had to hit up a renowned craft beer spot or two. The afternoon started with the Deschutes Brewery Portland location — a craft beer lover’s dream.  Lauded for rich, innovative and hard-to-find beers (at least back in NYC), I can’t recommend the nearly legendary Black Butte Porter or the Inversion IPA enough. It was a nice lead-in to another busy evening — centered, of course, around a trip to bustling sports bar The Independent to catch my beloved Michigan State Spartans take on the Notre Dame Fighting Irish! And for a postgame brew, I headed to 10Barrel Brewing, another Oregon favorite that’s always a treat to sip.

Heading back home in comfortable Standard Deviation denim, a classic Bridge and Burn tee and my trusty Huckberry Explorer’s Cap.

To kick off my last and final day in style — and with a jolt – I stopped by the Ace Hotel Portland, a hip boutique hotel that’s also a favorite spot in NYC for post-work drinks and small bites. Oh, and the coffee from Stumptown Coffee Roasters? It’s excellent, too. I also made my final day count in terms of #menswear, from my Astorflex Greenflex in Dark Khaki chukka boots to my slim, stylish and well-fitting Standard Deviation denim. Standard Deviation does it right when it comes to stylish denim — the brand’s Two-Part Solution allows you to try out two pairs for 15 days to nail down your perfect fit; when the time comes, you pay the discounted price of $78 per pair. Not bad, ehh? And certainly stylish for exploring Portland and heading to Ecliptic Brewing for a nice brew or two before a long flight back home.

I also dressed in laidback style with a new Bridge & Burn Basic Tee, a slim-fitting number made with a breezy cotton blend. The Heather Wine color  of the Basic Tee also played nicely off my Astorflex Greenflex in Dark Khaki chukka boots. Luckily, my essential Timex x Todd Snyder Military Watch ensured I stayed on time throughout the day.  For navigating a new city, reach for classic suede chukka boots and perhaps some favorite tunes, as I did when I plugged into stylish headphones from the Bespoke Post Vibes Box. With a busy, enjoyable and exciting weekend behind me, it was time all too soon to head hone. I appreciated Portland for its quiet atmosphere, its mix of amazing coffee, great menswear and live music, and the attention to detail in everything from food to craft beer. Is Portland “weird,” per se? It’s different than New York and Brooklyn, and that’s a great thing!

If you’ve got questions on the best things to do in Portland, drop me a note on Twitter. Follow along on Instagram for more men’s travel style tips, and check back tomorrow for a new #OOTD post.

Thanks for reading!

-Beau