From Squalor to Baller

Perhaps it’s because I just got back from a week in Montana, or possibly because I haven’t been getting dressed up much lately, but I’ve developed a hankering for denim and chambray shirts. Not the kind that you wear under a blazer – I’ve got those – but something deeply casual, well-worn, and with a bit of an “Old West” vibe. I am a Wild West kid, after all – my grandpa was a cowboy and my dad lived alone in the Oregon woods – so why not get in touch with my roots by spending too much money on a piece of clothing?

Maybe part of what is drawing me to Western shirts is how different they are from most of the causal shirts I own. Things like snap buttons, double flap pockets, and so forth never really make an appearance in my wardrobe, but they seem approachable enough for someone as mild-mannered as I am when it comes to clothing. I’d imagine that most authentic way to try this out would be to get a shirt in raw denim and and wear it until it breaks in beautifully, but I’m ok taking the shortcut here and going for something that already looks like it’s been beaten up for years.

My favorite western shirts are unsurprisingly from RRL, the grail brand for designer-level Americana and Western-inspired clothing. I will admit that I was probably 5+ years late for getting into RRL; I only came to appreciate the brand in the past couple of years when one of my coworkers familiar with the them turned me on to their products and showed me the depth to which the designers go to make the collections accurate and authentic-looking. RRL stuff has this way of looking like an amazing thrift store find and a designer piece at the same time, which is pretty amazing.

My current favorite is the Buffalo western chambray shirt (above left), and there’s also the classic Waverly chambray (which is a bit more toned down) and this paint-splattered option, which has its own thing going on. Any of those would be a fun addition to my shirt rotation, I imagine.

The issue with RRL, like with most high-end Ralph stuff, is the price. Their denim and chambray shirts tend to go from $200-300, which is a ton for an alpha-sized shirt that’s made in Asia. Be that as it may, they look great and it’s hard to ignore that.

Another great option comes from my good friends at Proper Cloth. I’m a well-documented superfan of the brand, and their recent dive into washed denim and chambray shirts definitely got my attention. I can’t think of any other company that offers made-to-measure washed shirts, especially given the great design details and solid prices that the company is known for. At first I wasn’t particularly interested since the design options were built around dress shirts, but earlier this year they released some more causal-oriented options – double flap pockets, snap buttons, and western front seams. These new additions make Proper Cloth a great option, in my mind. I don’t know if their shirts will ever have the level of character that the RRL ones do (out of the box, at least), but the value proposition just might be too strong to pass up. Proper Cloth just ended their most recent campaign on washed shirts, but I’d expect another one to go up in 3-4 months. Sign up to their email list to get notified (and be sure to use my referral code – $20 off  for new customers).

The wild card option comes from a brand that I’ve constantly complained about when it comes to shirts – J. Crew. My argument has always been that J. Crew’s shirt collars are too small to look good under a jacket, and I stand by that. With that said, a small collar feels right on a western shirt. A big 3.5″ Italian cutaway – or even a button-down with a nice roll – just doesn’t feel right on a shirt that already has so much going on. To me, a fairly subtle and soft point collar is the way to go. So in this instance – whether on purpose or not – it looks like J. Crew nailed it.

J. Crew recently released a surprisingly nice lineup of five shirts, that range from dark to light, and from all-out western to a bit more restrained options. Given that these range from $70-80 before the inevitable 30%+ off code, it may be hard to justify anything more expensive.

I’m not sure how well I’ll be able to pull off the shirts I mention here, but I’m starting to think that it’s worth a shot. Who knows – maybe next time I visit Montana I’ll be decked out in a western shirt, raw denim from LVC, and boots from Red Wing or some such place. I suppose that would make me both the most authentic and least authentic cowboy on the prairie, now wouldn’t it?