Thread by @dieworkwear

I agree. I mostly think the difference is generational. Although I wasn't alive in the 1950s, I admit that my taste runs "old." 🧵

When I was on a menswear forum, I once debated the same four guys for like eight months straight, arguing every day online, about how oxfords should be worn. In the end, one conceded that the only people he sees doing what I recommend are old guys at his church.

I hold that there was something special about the way tailored clothing was worn prior to the 1980s. First, the quality of the tailoring was higher; second, things were put together more tastefully (to my eye). This was true across racial and social classes

The book Black Ivy: A Revolt in Style by Jason Jules is about how Black men during this time wore things such as three-roll-two suits, rep stripe ties, and oxford button-down collars to both fit into and challenge the status quo. Think: jazz musicians, MLK Jr, Sidney Poitier, etc

In fact, Miles Davis was a famous patron of The Andover Shop, a menswear institution that sold Brooks Bros styled clothes to Harvard students. They also dressed famous Black figures such as Ralph Ellison, Albert Murray, and Bobby Short.

To me, this form of dress is quite beautiful. Here's Ralph Ellison. Notice that when he wears a jacket without the matching pants, it's a sport coat (e.g., tweed, blazer) and not a suit jacket. He pairs them with tasteful rep striped ties and a splaying Johnny collar.

Here's Richard Wright. Men today insist on wearing clothes so shrunken, they look like they're about to burst from their jacket. But Wright shows how elegant you can look in more comfortable cuts. The small details, such as the bow tie and reversed watch, are pretty great.

Many will feel these outfits are too conservative or "establishment." So how about James Baldwin? Even when he wears tailoring in a subversive way—such as a silk scarf jauntily tied around his neck—he still knows the difference between a suit jacket and sport coat.

Or Andre Leon Talley, who absolutely would have known that the jacket in the third slide has to be worn with the matching trousers, where as the jacket in the second slide can be worn with pants cut from a different cloth. Doesn't he look great?

Today, men across social classes wear tailoring in more "modern" ways. Some of these ways can be quite cool. Many of the ways look very ugly to me.

For years, people said that I simply don't "get" Daniel Craig's modern outfits and I was too old fashioned. Personally, I think he looks better now in a cut that's more classic. Jacket would be even better in a slightly mottled wool-silk-linen blend.

Same with Lebron. Twenty years ago, outfits like the one on the left were considered "modern." Now we look back and laugh. I suspect the outfit on the right will be considered cool for decades.

I also suspect most people will like this photo of Arthur Ashe taken ~50 years ago. Why? Because it follows some basic principles: shape and drape; sport coat (not suit jacket) worn with velvet pants; use of texture and pattern.

Unsurprisingly, this photo of Colman Domingo went viral some years ago. And look, it exhibits the same principles as Ashe's outfit. Silky, smooth fabric designates this as a suit, so jacket and pants are worn together. Shape and drape; use of texture in the overcoat.

I think it's a fair criticism to say that my taste in tailoring runs "old." So perhaps you will look like an "old man" following my advice. Personally, I don't understand why "old" is a pejorative, as many older men look great to me. IMO, this is very high level of taste:

I see younger men of all backgrounds wearing clothes using these same principles, and they always look great to me.

IMO, successful experimentation requires knowing a bit about the "rules." Notice here: none of these are just swapping out suit jackets for different suit pants. It's someone who's deeply familiar with the language of classic tailoring and can play with it in sophisticated ways.

Black velvet blazer teamed with a blue turtleneck and grey houndstooth trousers? Fantastic. Your blue suit jacket paired with your black suit pants and a white shirt with no tie? One wonders if you have a light in your bedroom.

Anyway, I agree that this is a generational thing. If you think there was something special about the way Cary Grant (and people of that generation) dressed, then I think the same principles can be used today to create classic and modern outfits in a way that's appealing

Please don't attack the OP, as my intent is not to create stress for anyone. But I thought their tweet was a good prompt to talk about how I think there was something special about an older way of dressing, and it hold some lessons that can be used today.