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Imagine my surprise, when I was scrolling through FT today. I recognized a name from this place, mentioned not only for his position in the Trump administration but also on the subject of menswear forums.

Can a Trump insider teach us anything about style?

https://www.ft.com/content/6cf18bda-326a-11e8-b5bf-23cb17fd1498

EDIT: I've copied the text of the article below, once I realized it was hidden behind a paywall

For connoisseurs of human oddness, the Trump administration has served a feast so sumptuous that some worthy dishes have received less attention than they deserve. Consider Michael Anton, former speech writer and spokesman to Rudy Giuliani, the second Bush administration and Rupert Murdoch. He wrote a much-read pro-Trump article, "The Flight 93 Election" - using a nom de plume borrowed from a Roman consul who sacrificed his life to ensure a great victory. The piece draped the standard case for Trump (boo free trade, boo immigrants, boo foreign entanglements) in a purple toga of muscular rhetoric. After the election, he landed a job as a face of Trump's National Security Council.

What gives Anton's case savour is his other life, outside of politics, as a dispenser of advice on style. On the menswear site Styleforum, where he writes as Manton, he has posted his thoughts 42,000 times, and gained a devoted following. Of course the correlation between a man's position on the political spectrum and his taste in clothes is tenuous, if it exists at all. Still, it is hard not to enjoy the image of some innocent, in search of advice about matching shoes to a suit, ending up in the sway of a nationalist PR man with intellectual pretensions.

I must admit I am touched by the thought of Anton, who cares deeply about clothes but is nonetheless willing to work for the worst-dressed rich man on the planet. He is a sort of minor political saint, submitting to humiliating association with the president's grotesquely ill-fitting suits and crass ties in order to serve his own notion of the common good.

I was so struck by Anton that, for the first time, I dove into the internet style forums he frequents. They have some unsurprising aspects. Men who are interested in clothes are also capable of rattling on to no end about steaks, high-end booze and cigars - the corny trinity of the masculine good life, as conceived by men of modest imagination. Other features were pleasantly surprising. There was less trolling than an earnest desire for answers and a genuine effort to provide them. Does this suit fit? No, the chest is shapeless and the legs need a taper, but a good tailor can fix it. Styleforum's tone is predominantly decent. That is more than I can say for the comments under FT articles, for example.

That said, the very idea of style advice is problematic. There is nothing wrong with the sort of nuts- and-bolts advice that style sites are full of (do not iron corduroy directly, even inside-out; put a cloth over it first or it gets shiny or misshapen). Nor is there anything wrong with anyone offering their basic rules of getting dressed (it looks silly if your pocket square sticks out too much, says Anton), or a discussion of whether one can get away with a brown suit at work (get a different job if you cannot, I say). All of this is good fun, useful, or both.

The problematic idea is that one person can teach another to be stylish: if this were so, there would be a lot more well-dressed people walking around. This is to be distinguished from one person being dressed by another. An excellent recent piece in the New Yorker tells of a man who makes a good living dressing Hollywood agents and the like (his advice seems to boil down to three points: wear clothes that fit; not everything has to be blue or grey; buy very expensive sweaters). He cannot make his clients stylish, however. Instead, he provides the service - one not to be denigrated in an industry of appearances - of putting them into stylish clothes.

Allow me to indulge in some intellectual pretence of my own. Socrates, in the Meno, pointed out that if virtue could be taught, there would be proven teachers of it, and every virtuous man would pass the secret on to his son. But there are not, and they do not. So it is, alas, with style. Definitions and rules fall short; put two people in a similar outfit, one looks perfect, the other foolish. Follow every rule, and you will be faulted for not breaking any. Break the wrong one, and the result is a disaster.

Is style innate, then? Not quite. Instead, acquiring style in dress is similar to developing style in prose. The steps are imitation, failure, revision. We admire someone - not on the internet or in a magazine, but up close and in real life - and we try and dress like them. The effort fails. We make a change, fiddle around, make another change, and maybe get somewhere. Advice is mostly futile. The best one can hope for is that the process itself does not destroy the confidence that is necessary to keep going.

 

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And I believe that last phrase is the critical one. One must have self-confidence to keep going and that simply cannot be taught. Style is something that radiates, whether we like it or not, from the inside out.
 

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^^+1. My friend you have hit the nail directly on the head and you did so with far fewer words than did the author of the article quoted in the OP. It all boils down to the personal presence one is able to project. Now if y'all will excuse me, I think I'll take a stroll in a pair of my western boots....who doesn't love a cowboy? ;)
 

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Interesting post and a concise reply by Sarg.

One's personal style develops over time based on influences, as for myself it lies in detail. I like knowing that the only people who may notice the attention to detail are the like minded,....
 

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A lot of people here have given advice.
Manton has written extensively here in the past. He has done tremendous amount of reading on the subject. History has presented a lot to think about. Some people have lots of talent with styles, and then there are people on the other end. Most people fall somewhere in between. Pretty much for all there is a learning curve. Although, for some it is helpless. Rules are guides that help. Being able to write well about it doesn't mean they're good at their own styles. Knowledge is knowledge. Putting the knowledge to work is something else. Manton certainly pushes drape. But, that's not all he knows.

Why would the writer of the article think Monton wouldn't have a number of interest? It looks like another democrats attack on republicans.
 
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