At a certain point, dressing with a fondness and knowledge of traditional men’s clothing can become staid. I have referred to this previously as the point at which style becomes costume. The instant you start wearing a bowtie with your tweed jacket and flannels. The moment when you add a tie pin to your three-piece, double-breasted suit. At this point you are merely aping the dress of a certain period, and dressing up for pantomime.

The traditional must be balanced with the quirky, the modern and, most importantly, the personal. Wear beaten-up converse under your flannels. Add a lurid handkerchief to your suit’s breast pocket. The true enthusiast of style is constantly striving to update these traditions and add a twist. This does not mean having a buttonhole stitched in a contrast colour, or going for a bright jacket lining, a la Paul Smith. It has to be your own. It has to be personal.

Here are a couple of recent inspirations of my own. They both balance ties, either necktie or bowtie, with more casual pieces of clothing. As the tie is towards the formal extreme of a formality spectrum, it should be balanced with something from towards the other end of the spectrum, the informal.

Two provisos. One, this assumes that the look you want is somewhere in between: a weekend or casual Friday look with a formal edge to it. Two, these suggestions are obviously not that personal, given that I am suggesting them to you. But they’re perhaps a good place to start.

My first combination comprises Oxford button-down shirt, bowtie, jeans and hooded sweatshirt. I have no opinion on the shoes – perhaps brogues or trainers, depending on your mood. In fact, the shoes are probably the tipping point of formality: formal with an informal twist, or the other way around. The bowtie at one end of the spectrum is balanced by the hoodie at the other end. The Oxford-weave shirt, similarly, makes an effective background to the bowtie.

The second combination is another version of the same idea. Necktie with Windsor-collar shirt, jeans and rugby shirt. In this instance, the necktie is balanced by the rugby shirt. The tie should be a casual fabric if possible – cotton, linen, wool. Something matte. The rugby shirt is something of a British institution but is also fairly widely available in the US. An equivalent is the long-sleeved version of the polo shirt.

Preppy combinations, perhaps. But pulling them off well, personally, is your job.

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Arctic Penguin

Simon,

As an American I sense a certain tragic disparity between your advice and the execution of said advice by persons to be found on the street, that is to say, persons found outside of photo shoots and magazine spreads. Nonetheless, I find it easy to believe that you could pull this off, but it seems to be an almost ineffable ability we Americans typically attribute to foreigners (especially Europeans.. sorry if you as a Briton bristle at being grouped in with the Continent) and models.. But more and more men, especially younger men, seem to be paying better attention to fit which is perhaps the one greatest point in style which separates those in the photo spreads from the rest of us. I think your blog is helping to bridge that gap.

Clinton

Simon,

I appreciate your suggestions. I’ve actually been kicking around the idea of bowties for a while now, but, because of my location, good ones are hard to find. When my sewing machine is put back together I’m going to rip apart some thrift-store ties and turn them into bowties.

Also, I just wanted to let you know that I appreciate your attempts to be a little more creative with your sense of style. I think too often men (even those interested in “style”) get caught up in the “rules” and “what goes with what.” I like to see people acknowledging but purposely flaunting those rules. As I see it, style and fashion are supposed to be fun and blue suit, light shirt, dark tie, brown shoes can only be fun so many times before it turns into just more of the same.

Carry on!

Clinton

Easy and Elegant Life

Rugby shirts under our blazers or tweed sportcoats were a winter staple at my secondary school. The shirt was always a button down with a bow or four-in-hand tie. It was a good look and one that works well for weekends, up to a certain age. On weekends at the football game, we would wear a (grey) hooded sweatshirt (no zipper) under the (brown herringbone) tweed jacket and jeans or khakis. LL Bean hinting shoes, no socks, rounded things out.

Anonymous

“Oxford button-down shirt, bowtie, jeans and hooded sweatshirt”

Oh wow, just imagining that makes me smile. It sounds fantastic but I would never have the balls to pull that off. That said, I am one of the younger men you often refer to who are just discovering an interest in style and feel fairly self-conscious just wearing something slightly different. I can’t wait for the days where this stuff becomes a part of me and I can wear it with nonchalance.

One problem I have is that casual wear is so much more open than formalwear. It’s easier, I think, to produce a smashing combination of suit/shirt/tie because you’re restricted. With casualwear, anything goes and I feel as though this makes it a bit intimidating to experiment as there is a much higher scope for error.