Menswear Style | The Rules of Engagement


One thing I think we can all agree upon– the hard & fast rules of menswear past have pretty much been shot to death.  Personal preference (with good & bad results) seems to dominate today, and the media darlings (celebrities, designers and God forbid– celebrity designers) have done everything in their power to erase what was good and leave their own mark on fashion & style.  The funny thing is– there’s still very little individuality worth noting.  And the real irony– conformity is still largely present, it’s just that there are more uniforms to choose from, which sometimes requires a little more effort to pinpoint the reference– but in large part it’s still a game of follow the leader.  We can all name and probably fall into some of the new categories– the “heritage brand hipsters”, the “denim fetishists”, “the skinny jean rocker”, “the Kanye”,  and the list goes goes on and on and on.

Esquire did a list last year on the new laws of casual style.  With things moving at light speed today, it would be interesting to see which, if any, still hold up?

And we’re talking style, not fashion.  The top picture of plaid man represents fashion– the image below of Kirk Douglas is pure style.  The skinny belt is back, btw.


sartorialist plaid man menswear

Kirk Douglas.  Pattern mixing was big for Fall, with guys everywhere layering tartans and buffalo checks-- but beyond the "in your face" look is the subtle art of the gentleman who can do it with a much more subtle and dapper affect.

Pattern mixing was big for Fall, with guys everywhere layering tartans, buffalo checks, etc. But beyond the “in your face” look is the subtle art of the knowing gentleman who can pull it off with a much more subtle and dapper effect by choosing patterns that complement, not compete– but you have to know the rules. The Glen plaid acting very much like a solid in terms of scale and color, adds interest and texture where it would have been just as easy to pair the bold plaid with a solid grey flannel trouser and call it a day.



1. When in doubt: a white oxford shirt.

No argument there.  Heck, even The Sartorialist agrees– it must be so.  If that’s not good enough for ya, how about preppy icon JFK? 

the-satorialist-gap-scott-schumanJFK white oxford shirt menswear

7. A rugby shirt is the most masculine thing a man can wear.

Hmmm.  The Rugby shirt, which I love, seems to be something you either get or you don’t.  Masculine, sporty and steeped in heritage.  It can also look good dressed up– yep, there’s a rugby under there.  He reminds me the group of guys below– spectators at an Oxford rugby match, c. 1939.

Antonio RugbyOxford rugby match

8. The 1950s and 60s were the high points of casual. Everything before and after was hit-or-miss.

Well, I know what you’re saying.  There was a coolness and an almost naivete that is very appealing.  We’re talking early 60s though, right?  Because it started to get hit-or-miss in the 60s too.

bermuda shorts menswear 50s fashionhippie menswear fashion 

14. Justin Timberlake doesn’t look quite as good as he thinks he does.

Amen to that.

Justin Timberlake GQJustin Timberlake GQ


22. Always tuck: polo and dress shirts that hang below your hip. Never tuck: sweaters and turtlenecks. Everything else is negotiable.

Some style icons past (Clark Gable) and present would disagree.  I’m a big fan of the tuck.

Clark Gable


69. There’s not a whole lot of room for irony or imitation in style. The best-dressed men always dress like themselves.

A pretty good rule to end on, and very good advice indeed.  Fashion is imitation, style is essence.

6 thoughts on “Menswear Style | The Rules of Engagement

  1. You hit the nail on the head with my two “go to” items. The White Oxford shirt (wearing one today) and a Rugby shirt (probably wearing one tomorrow). These speak style and ease… To many people try to get “tricky”. What about good old American (or English) classics? Dress them up, dress them down. Thanks for the post.

  2. My God, How boring and predictable, a white shirt? Please.

    Why say there are no rules then underline the most obvious basic rules that have been shoved down mens throats for years? Things in your opinion may have become hit or miss after the 60’s but that is when people also stopped becoming cardboard cut-outs of each other!

    The whole point of personal style and expression IS that not everyone will like it. These rules you have again spelt out, aren’t for men who are interested in fashion, this I agree, but they are also not for anyone interested in style.

    These rules are for men who don’t have a clue and just want to leave their house half decent without embarrassing themselves. This I don’t have a problem with, when it’s for convenience, comfort or not having to THINK at all about what to wear, but don’t confuse it with style.

    Enough of Polo shirts, Oxford shirts and boring chinos. All of these English styles “borrowed” from the British heritage and have been flogged to death. Seriously can people not think of anything new to wear? Even the renownedly stylish English don’t wear them any more. Is this all there is to American Style??

    To be truly stylish is to show flair and personality not to look like you just fell out of a Gap, Ralph Lauren, J Crew, Tommy Hilfiger, Brooks Brothers etc etc ALL selling exactly the same thing, and have been for years, year in year out!! Men in their 20’s dressing exactly the same as men in their 50’s?? What’s that about?? So in the end you’ve gotten your wish, card board cut-out from the 60’s are alive and well and walking among us all.

  3. Petzi-

    Ease up on the espresso, buddy. That’s an awfully strong reaction.

    I was just simply underlining a few obvious points that the Esquire article made- not extolling the virtues of their high style. You are correct- there is a lot more to American style, obviously this was just a primer. I get the flair thing, thanks.

    All that aside, I do appreciate your feedback.

  4. What can I say, I’m passionate about fashion and design and in particular fashion that is designed rather than garments just repeated to death under the heading of classics. It’s too easy now days to label something classic and just repeat the same style for the 100th season without considering the cut, cloth or bespoke details to give it it’s worth to the customer, just because they think the average customer is too stupid or doesn’t care or notice.

    It even goes back to an article you wrote previously about merchandisers becoming designers and in particular Michael Bastian, yet another person flogging the same thing that I spoke about, that we are meant to believe is different just because he has a different stylist.

    Or even celebrities who become so called designers and have their own line and we are meant to believe they actually wear the clothes, like Sarah Jessica Parker doing a line with Steve and Barry “every item under $20” when she wears couture and designer labels constantly or people like Puff Daddy who at least pretends to have a higher line but is in the front row of other designer shows wearing their clothes! Where has the integrity gone? Do all these people really believe that the customer is that stupid or are they just milking their stardom for all they can get? MMnnn I wonder.

    I am just dismayed at the state of the fashion industry at the moment. Those who are truly creative and are striving to create something new and original for today, to mark the new century with it’s own distinctive style (like the designers in their era did for the 60’s) are being swallowed up or over shadowed by the big companies who produce the same thing year in and year out or celebrity lines milking their fans until they get bored and walk away leaving the real designers who designed the clothes out of work.

    It is the new creative designers that should be championed, and challenge those who have been dressing the same for so long to think differently and point out the greed and callousness and how they’ve been manipulated. Let’s look to the future rather than the past to see what we will be wearing.

    Oh and I don’t drink coffee…. but I’ll have a cup of tea though ; )


Comments are closed.