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Lookbook: Dressed Up Casual

February 26th, 2013

This is a great first “lookbook” post since it combines a few elements featured on the site yesterday—a gingham pattern, one of my favorite pocket squares, and a grey donegal tweed suit jacket. And it’s also a great starting point to showcase something I will definitely keep coming back to over and over again, one of my key style and menswear values: versatility. Each of this look’s main elements—the tweed suit jacket, gingham shirt, and raw denim jeans—are pieces that can be used in any number of combinations in any number of situations. All it takes is a little creativity, adventurousness, and a willingness and openness to mix pieces in different and/or unexpected ways.

Business Casual - He Spoke Style

Dressed up casual definitely sounds like an oxymoron. It’s sort of like trying to figure out the difference between partly cloudy versus mostly sunny. And in a way, it depends on how you look at it or what your frame of mind is when you’re making the determination. In terms of this look you could say I’m dressing up the denim or dressing down the suit jacket. Either observation would be correct. But mostly this look is a balancing act between the more dressed up elements—tweed suit jacket, tie, and black penny loafers—and the casual ones—denim and watch strap—with the gingham shirt acting as the glue that holds everything together. You could also call this look business casual.

Business Casual - He Spoke Style

Never underestimate a watch strap’s ability to completely transform a look. I had a black strap fastened from over the weekend but thought it would tip the look a little too much to the dressed up side for what I was feeling. The olive provides a subtle bit of contrast to the look’s prevalence of grey and blue, while the red stripe is a nice accent that picks up the color of the pocket square and socks while not being overbearing or overt.

Business Casual - He Spoke Style

Stylishly Yours,

He Spoke Style

This look: Grey donegal tweed jacket by Brooks Brothers (part of suit), black gingham shirt by Express, raw denim jeans by A.P.C. (New Standard), black belt by Perry Ellis, burgundy pocket square and wool striped tie by The Tie Bar, watch by Timex, olive and red NATO G10 watch strap by J Crew, burgundy socks by Polo Ralph Lauren, black penny loafers by Bass Weejuns.

Brian Sacawa

Brian Sacawa is the Founder of He Spoke Style and one of the original men’s style influencers. Since 2013, his goal has remained the same: to provide men the advice and inspiration they need to dress well, develop their personal style, and gain more confidence. Brian’s interest and passion for men’s style and luxury watches has led to his writing for The Robb Report, The Rake, and Sotheby’s and he has been quoted on menswear in publications such as The New York Times, The Wall Street Journal,, Brides Magazine, and the Huffington Post. He lives in the woods north of Baltimore with his wife, Robin, kitties Nick and Nora, and German Shepherd/Collie mix Charlie.

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Like the tie bar, the pocket square is a classic and timeless menswear detail that has made a comeback in a huge way. Thankfully, guys are discovering that they are allowed to rip out the stitching of their suit jacket's breast pocket and fill it with a small accessory that makes a big impact with a high style reward.

A pocket square improves a suit jacket or blazer's versatility, adds visual interest and depth to a look, and provides a subtle but powerful means of personal expression. There are many ways to fold a pocket square—some simple and some more complicated—but how you choose to rock it depends mostly on personal taste (and slightly on the degree of formality of the occasion). As with anything, practice makes perfect and a little time invested in the skill upfront will ensure you can wear the pocket square any way you want with ease and flair. Here are five of the folds I use most often and that are guaranteed to have you covered from casual to formal.