Sneakers With Tailoring: Yes, No, Maybe?

[Waldo Jeffers]

I can’t believe that you literally operate with zero rules on how to dress. You just are unaware or unwilling to admit it. Do you just randomly pick items from your wardrobe to wear on a given day? If you are interviewing for a job, do you really not think at all about what to wear and why? Can’t take you seriously at all.

so dramatic!

I have my own ideas. I try to find what works for me. I don’t claim that what works for me are rules for humankind like some mystical clothes guru

 

[dieworkwear]

so dramatic!

I have my own ideas. I try to find what works for me. I don’t claim that what works for me are rules for humankind like some mystical clothes guru

But this is not true, as you just gave a rule. People who are not rockstars should not wear yellow suits. This is now a rule. You didn't say, "I don't like yellow suits on me but can't say for other people." You created a rule by qualifying the people (non-rockstars) and the action (don't wear yellow suits).

I think the point is that even people who say they're not for rules have their own rules.

 

[breakaway01]

so dramatic!

I have my own ideas. I try to find what works for me. I don’t claim that what works for me are rules for humankind like some mystical clothes guru

Okay so you do have your own “ideas”. I think these are normative rules. “This looks better than that”. I can understand that your “ideas” might not match mine. I just think that to become a better dresser, one should understand one’s own internal ideas/rules/whatever and be willing to question them. If you can’t articulate what they are, it’ll be hard to improve. And if you don’t want to improve, then again I kinda question why you’re here.

totally honest, although some of this debate is a little painful I have to thank you and @dieworkwear for making me examine my own ideas about dressing in a more intentional way.

 

[Waldo Jeffers]

But this is not true, as you just gave a rule. People who are not rockstars should not wear yellow suits. This is now a rule.

I think the point this that even people who say they're not for rules have their own rules.

You can of course decide the appropriateness of a yellow suit for your personality. I’m not making a rule, judge for yourself. However, if the only examples you can show of men looking good in this are rock stars, then you are showing the limited range of this outfit

 

[dieworkwear]

You can of course decide the appropriateness of a yellow suit for your personality. I’m not making a rule, judge for yourself. However, if the only examples you can show of men looking good in this are rock stars, then you are showing the limited range of this outfit

This is also a rule! You are saying that yellow suits have qualifications in order to be worn well. So then we can ask what are those qualifications? Seemingly, "be a rockstar."

It's not a random aesthetic judgment, right? You can kind of guess whether someone will look good in a yellow suit. And thus, that's the rule.

 

[Waldo Jeffers]

Okay so you do have your own “ideas”. I think these are normative rules. “This looks better than that”. I can understand that your “ideas” might not match mine exactly. I just think that to become a better dresser, one must understand one’s own internal ideas/rules/whatever and be willing to question them. If you can’t articulate what they are, it’ll be hard to improve. And if you don’t want to improve, then again I kinda question why you’re here.

To analogies to music, if it sounds good, it is good. The audience does not give a sh-t what theory is underlying the sound. You can have some elaborate theoretical justification for why your music is great, but if the audience doesn’t like it, it is irrelevant

again, I’m here to see people ideas. I do learn from people here, but not from these attempts at theory. The theory does not matter

 

[dieworkwear]

To analogies to music, if it sounds good, it is good. The audience does not give a sh-t what theory is underlying the sound. You can have some elaborate theoretical justification for why your music is great, but if the audience doesn’t like it, it is irrelevant

again, I’m here to see people ideas. I do learn from people here, but not from these attempts at theory. The theory does not matter

I don't think you operate like this, however.

If I said, hey Waldo, I'm going to a dinner and thinking about wearing a chicken suit. You wouldn't say "well, I have to see the chicken suit on you first before making an aesthetic judgment." You would say, "that's a bad idea" even without seeing me in this chicken suit first.

We can reel it back. I can say "I'm thinking about wearing a purple suit." Or "I'm thinking about wearing a suit jacket with swim trunks." You would never say, "I can't make a judgment because I can only judge once I've seen something on you." You have in your mind what's a good style. And that's governed by ideas or rules about dress.

 

[Waldo Jeffers]

This is also a rule! You are saying that yellow suits have qualifications in order to be worn well. So then we can ask what are those qualifications? Seemingly, "be a rockstar."

It's not a random aesthetic judgment, right? You can kind of guess whether someone will look good in a yellow suit. And thus, that's the rule.

it’s a rule in the sense that it’s driven by the personality of the wearer, which is what I’m saying is the only actual rule

 

[Waldo Jeffers]

I don't think you operate like this, however.

If I said, hey Waldo, I'm going to a dinner and thinking about wearing a chicken suit. You wouldn't say "well, I have to see the chicken suit on you first before making an aesthetic judgment." You would say, "that's a bad idea" even without seeing me in this chicken suit first.

We can reel it back. I can say "I'm thinking about wearing a purple suit." Or "I'm thinking about wearing a suit jacket with swim trunks." You would never say, "I can't make a judgment because I can only judge once I've seen something on you." You have in your mind what's a good style. And that's governed by ideas or rules about dress.

It’s really governed by my idea about who you are personally

Ashton Kutcher could probably wear something absurd to any party and women would love it

normal people have to be more careful

is this a rule— I guess. But it is really driven by who you are, which is very hard to generalize as a rule about these abstract items go with these other abstract items

this obviously greatly complicates the issue and I understand many would like there to be easy answers you could regurgitate for some imaginary exam

 

[breakaway01]

To analogies to music, if it sounds good, it is good. The audience does not give a sh-t what theory is underlying the sound. You can have some elaborate theoretical justification for why your music is great, but if the audience doesn’t like it, it is irrelevant

I love that you picked a music analogy because I think it has some great parallels with dressing well.

Do you play any music? It is clear you do not. Doesn’t matter the genre, if you do not have a sound understanding of the underlying theory you won’t sound good. It’s not elaborate, but actual musicians do know and apply music theory. Do you think a jazz improvisation or a rock guitar solo is played without an underlying rhythm and chord structure (chord progression)? Or maybe you really just have no idea.
Now, based on the rules, you can personalize your music and be different. But it does start with understanding some (actually many) normative rules about music.
So yes, the audience might not understand or care, but if you play music with no rules you will very likely sound terrible. If you apply the rules, you still might not sound amazing but you probably won’t sound terrible. If you apply the rules and are talented, you might sound great.
Even cool musicians like Mick Jagger follow these rules, believe it or not.

 

[dieworkwear]

It’s really governed by my idea about who you are personally

Ashton Kutcher could probably wear something absurd to any party and women would love it

normal people have to be more careful

is this a rule— I guess. But it is really driven by who you are, which is very hard to generalize as a rule about these abstract items go with these other abstract items

this obviously greatly complicates the issue and I understand many would like there to be easy answers you could regurgitate for some imaginary exam

How can you make aesthetic judgments online? None of us know each other in any meaningful sense. Even beyond the small circle that's discussing things in this thread, how can you look at random photos of people online and make judgments about their dress since you know nothing about their lifestyle, social circle, and personality?

And even when the outfit accords with the person's personality, can we not say that an outfit is ugly? Roger Stone dresses in a way that's perfectly "Roger Stone." Do we then say "his style is good because it's a reflection of him?" Or do we say, "yes, his outfits reflect him, but he has terrible taste?"

 

[mjs]

I like to look at different ideas

I’m not really interested in claims about rules. I don’t really think they exist in real life. I think the people who insist they do exist generally look forced.

I think the only reality is what looks good. And realistically, what looks good is primarily determined by the person wearing it, not the clothes themselves

so I think the key if you are not extremely good looking, is really to figure out what is congruent with who you really are

not to try to wear some costume based on abstract fake rules

you can look at other people who maybe look like you and say, is that me too?

that is not theorizing. That is about seeing examples of real life execution

I'm not sure you really believe this, you just think you do.

Say you are in a business meeting and you notice one of the new junior hires in accounting seems to be dressed oddly. You wonder what looks off about his clothes and realize it’s because they are two different colors and patterns, split down the middle. One leg of his trousers is pinstriped gray flannel, the other leg is navy blue.

One side of his shirt is sky blue gingham, the other side is light pink. One of his shoes is black, the other is burgundy.

One side of his jacket is pinstriped gray and the other side is navy blue, but it’s opposite to the pants.

He has two neckties on one over the other, with one tucked under one arm and the other going under the other. One is paisley and the other is polka dotted.

Half his head is shaved and tattooed with a pattern that looks like a chessboard, and you can’t see the other side of his head because he's got a baseball cap on, but half of it is cut out so you can see his checkerboard tattoo.

You look at his chair and see that he's draped a cape over it. One half of the cape is embroidered with lions and the other half with what looks like the planet Saturn and stars, and rocket ships.

He’s also propped two umbrellas against his chair. One has a handle shaped like a rocket ship, the other like a lion.

How do you think he looks?

 

[Waldo Jeffers]

I love that you picked a music analogy because I think it has some great parallels with dressing well.

Do you play any music? It is clear you do not. Doesn’t matter the genre, if you do not have a sound understanding of the underlying theory you won’t sound good. It’s not elaborate, but actual musicians do know and apply music theory. Do you think a jazz improvisation or a rock guitar solo is played without an underlying rhythm and chord structure (chord progression)? Or maybe you really just have no idea.
Now, based on the rules, you can personalize your music and be different. But it does start with understanding some (actually many) normative rules about music.
Even cool musicians like Mick Jagger follow these rules, believe it or not.

oh I’ve been called out

i play guitar pretty decently. I understand chord progressions

I also understand that a lot of the most influential music has been made by people who have zero abstract knowledge of theory

did they apply it without knowing it— sure. But in many cases their lack of knowledge caused them to violate purported rules which made their music interesting and unique

so maybe don’t get so hung up on the abstract stuff. It is not the most important part thing

 

[Waldo Jeffers]

I'm not sure you really believe this, you just think you do.

Say you are in a business meeting and you notice one of the new junior hires in accounting seems to be dressed oddly. You wonder what looks off about his clothes and realize it’s because they are two different colors and patterns, split down the middle. One leg of his trousers is pinstriped gray flannel, the other leg is navy blue.

One side of his shirt is sky blue gingham, the other side is light pink. One of his shoes is black, the other is burgundy.

One side of his jacket is pinstriped gray and the other side is navy blue, but it’s opposite to the pants.

He has two neckties on one over the other, with one tucked under one arm and the other going under the other. One is paisley and the other is polka dotted.

Half his head is shaved and tattooed with a pattern that looks like a chessboard, and you can’t see the other side of his head because he's got a baseball cap on, but half of it is cut out so you can see his checkerboard tattoo.

You look at his chair and see that he's draped a cape over it. One half of the cape is embroidered with lions and the other half with what looks like the planet Saturn and stars, and rocket ships.

He’s also propped two umbrellas against his chair. One has a handle shaped like a rocket ship, the other like a lion.

How do you think he looks?

this isn’t a real life example obviously

There seems to be some claim here that ordinary people have zero idea how to dress. They are like savages and the CM theorizers have to convert them to the Rulez

most people dress ok for the lives they lead. They don’t try to dress like rock stars or 1930s City of London financiers because they understand their actual reality

could they benefit from a little inspiration- probably

but the fundamental assumption here that they are clueless is pretty ironic

 

[TheShetlandSweater]

Not gonna lie, I understand now why DWW is so adamant about this topic. The people on the positive side have just no eye for what looks good. All the photos were just absolutelly terrible, expecially the oxfords with jeans. Oxfords, under no circumstance or form can be worn well with any kind of jeans. There's too much discordance between the formality of even the most casual oxford and any kind of jean.

When this whole debacle started I was against his "rule", but when I think abouth oxfords worn casually I'm thinking about this kind of oxfords worn like this. View attachment 1682282 View attachment 1682283

And no, swapping the flannel trousers for jeans would ruin the whole damn thing.

Simon's choice of shoes here is bad, IMO.

Oxfords do well with a sleeker silhouette and long lines. That's a big part of why they work well with suit and tie. Slightly less well with suit and no tie. Sport coat + trousers = less sleek and shorter lines, and that's why oxfords don't do as well here. Oxfords in the right shape, material and color could work with the trousers and a shirt (because the silhouette is sleeker without the jacket). but you have to get the details just right.

I have a pair of mid-brown suede oxfords from Lof and Tung. They don't have a ton of shape (which is part of why this would work). Have a round toe. Heel is relatively low. I think they would work well with dark grey high rise trousers in a slimmer cut and a university stripe OCBD. Maybe a summer look. But if I were to throw a shetland on top, that would bulk it up and make it not work.