Real People: Learning To Dress Casually

December 28, 2015

Real People: Learning to Dress Casually

For a lot of guys, learning how to dress well begins with a coat and tie, then they move to casualwear. Part of that is because tailored clothing has clearer guidelines – you need a suit, a navy sport coat, and some grey wool trousers; pattern matching requires variation in scale; and clothes need to fit within certain parameters. Casualwear, on the other hand, can be a lot more interpretative, so the burden of figuring out what to wear is largely placed on you. 

Gerry in Melbourne picked up his interest in casualwear when he started realizing he needed a different wardrobe for weekends. “I was wearing a suit every day to work, so I learned the basics of fit and how things should be worn. Somewhere along the way, I realized I had a pretty good handle on what to wear most of the week, but no clue as to how I could carry that into the weekend without looking overdressed.” 

So, Gerry started paying attention to casually-dressed guys on Instagram (e.g. c_kimber, jcklh, urbancomposition, cotton_dockers, and alessandrosquarzi). Since then, he’s developed a kind of style that can be described as Japanese/ European workwear mixed with things Steve McQueen might have worn. In the above, he’s paired a Le Laboureur chore coat and an Engineered Garments field parka with flat-front chinos and moleskins. For a slightly more comfy look, he wears a chunky shawl collar cardigan with Orslow jeans, a plaid shirt, and some shell cordovan bluchers. The colors are all muted, but the subtle play on textures keeps things interesting. 

As a guy who still mostly wears suits and sport coats, Gerry is careful about choosing things that can work in a number of contexts. His country grain chukkas, for example, can be worn with anything from beat-up denim to dressier wool trousers. The navy parka above can also be swapped out for a sport coat if he needs to look more tailored. In this way, Gerry didn’t need to build his wardrobe from scratch – he just added a few key pieces here and there to give his wardrobe better flexibility. 

So, since he’s started dressing more casually, what kind of items does Gerry find most useful?

  • Dark Brown Suede Chukkas: “These go with anything from denim to chinos to odd trousers and I can dress them up or down as I like. I have two pairs – the dressier of the two is made by Carmina and I have a pair by Christian Kimber on a more casual last.”
  • Engineered Garments Field Parka: “It’s warm, looks great, and has a ton of pockets – some of which I’m still discovering. The pockets come in handy when I’m out shooting photography. I can pack a spare lens or compact camera in the parka, then carry my main camera on a shoulder strap. The alternative is my olive Engineered Garments mountain parka, which serves the same purpose during the warmer months.”
  • Chinos: “A staple that goes with most of my outerwear, whether it be a leather jacket, a nylon field jacket, or a linen shirt jacket. I have a pair from Boglioli in a lightweight cotton fabric and a heftier pair from a local store called Up There.”
  • Oxford Cloth Button Down Shirts: “Again, these go with everything – denim, chinos, and wool trousers, as well as any of my jackets. I have a couple of white OCBDs from Brooks Brothers and Engineered Garments, and then a blue one from Kamakura.”

Granted, everyone’s list of favorite casual items will be different (that’s what makes casualwear fun), but as Gerry has proven, you can learn a lot by first noticing what other well-dressed guys wear, then adding your own touches. 

To see more of Gerry, you can follow him on Instagram and Tumblr. He also has a blog for his photography