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How to stop overdressing

jko

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Not sure I completely agree. I do dress for myself. It's a form of self-expression. However, I choose to include the constraints of the "Overton window" in my dress. IOW, I care about context when I dress. I enjoy the challenge of solving the multi-constrained problem. BTW, my solutions aren't always on the mark. 😆
I should've clarified, people who say they dress for themselves only. You need a bit of both.
 

imatlas

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I've had a lot of thoughts about why some people are so happy to get out of the "boring" suit, and I have a couple of thoughts:

1. To a lot of people, the suit was forced upon them. "Nice" clothes in general is something many young men are taught to fear: you are forced to wear them for events that you are forced to go to, where you're suppose to sit still and be good. You may have to eat food you really hate, and pretend to be happy to see people you can't even remember. You might get your cheeks pinched by your aunt.

At work, it doesn't get any better. To most people, the suit was something you were forced to wear 5 days a week. Just like many #menswear guys chafe at the idea of having to wear slim fit, poly blend polos to fit in, many men chafed at having to put on a suit they hated.

2. Suits are extremely uncomfortable if they don't fit, and most people don't know the first thing about fit. This goes for people selling clothes as well as people buying them.

In our little bubble of guides and googling, it's sometimes hard to forget how much of this knowledge of cut, fit and make is esoteric knowledge. Just like not everyone knows how to compile their own UNIX kernel (disclaimer: I have no idea what a UNIX kernel is, or if one in fact does have to compile ones own - it just sounds like a suitably arcane technical thing), not everyone knows where to shop for a good suit, and what to ask for to get one. Many people still believe that if you go to a fancy store and ask the beautiful people who work there what to get, the expensive rags they sell you will be as good as it gets. And if you just paid 3 000 for a fused, slim fit poly blend suit, you're unlikely to feel very excited about tailoring either.

Putting these two together, I can see why Daniel Craig might enjoy getting out of the suits: he's been forced to wear too-slim, too-short suits for work for years. Tom Ford has a lot to answer for!

@ppk Yeah, I'm a consultant too. It definitely makes it easier when you're already outside of the normal power structure, and not expected to be part of an established team.
Solid analysis.
I've never seen a suit when conducting an interview myself either.

Literally never? That's bizarre. I've worked in Silly Valley for decades and have always worn a suit to be interviewed, or at least a jacket and wool trousers, and I expect to at least see a sportcoat and collared shirt when I'm interviewing someone. I wouldn't make a hiring decision based on their attire, but if someone shows up looking like a slob I will definitely consider it a sign that they can't be bothered, and I'd wonder what else they can't be bothered with.
 
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Summed that up perfectly.

The bit about NOT potentially hiring you for wearing a suit is somewhat eye raising - were these managers ahem 'socially maladjusted' ... unless you are going for a trades related position you should ALWAYS wear a suit ... otherwise you are basically showing disrespect to the interviewer/panel/firm from your slovenly attitude.
From the interviewer side of the equation - not at least wearing shirt/tie/shoes you were already in the unlikely pile in my view.
At an interview you are showing at the basic level the ability to impress - I'm sure you can borrow the attire if you don't own it. Not hard.
Both of those managers had the gift of maintaining a permanent state of being of "the barista screwed up my esoteric coffee order" and took out everything on everyone around them. I'm glad I didn't work with either of them for very long.

If people ask me about my choice of clothes, I just tell them "I like suits". If they're actually curious, I'll also share the story of the difficulty of finding clothes that fit off the rack, and the difference in comfort between slim jeans (terrible) and bespoke trousers in soft flannel (amazing). "Some people buy season tickets, some people have a Tesla, I have a nice wardrobe."

It helps to start at day 1: if you show up wearing tailoring and just keep doing it, people get accustomed to it pretty quickly. If you start doing it after a while, people seem to respond worse. I've never received any criticism at work, but one of my best friends from university shakes his head every time he sees me and says I've sold out (I quite wish it was a case of SELLING out - I'm doing the buying here!) If people get to know you as the "suit guy" from the start, it's much easier to get away with it. Wearing tailoring might get you looked at a bit differently, but I don't think that has to be a bad thing.
I definitely experienced this. Doing it after I had established a different look from when I started drew a lot of attention.

2. Suits are extremely uncomfortable if they don't fit, and most people don't know the first thing about fit. This goes for people selling clothes as well as people buying them.

In our little bubble of guides and googling, it's sometimes hard to forget how much of this knowledge of cut, fit and make is esoteric knowledge. Just like not everyone knows how to compile their own UNIX kernel (disclaimer: I have no idea what a UNIX kernel is, or if one in fact does have to compile ones own - it just sounds like a suitably arcane technical thing), not everyone knows where to shop for a good suit, and what to ask for to get one. Many people still believe that if you go to a fancy store and ask the beautiful people who work there what to get, the expensive rags they sell you will be as good as it gets. And if you just paid 3 000 for a fused, slim fit poly blend suit, you're unlikely to feel very excited about tailoring either.

This is very true and something I was a victim of for far too long. Once I learned about proper fit and started buying things that were both well made and well tailored, a suit became my favorite garment to wear. Just the high armholes alone were life changing.

Like you said, there's a lot to learn about this space and while it makes a big difference to your wardrobe when you have that knowledge, it's hard to expect most people to make the investment.

So:

The point of this insight to me is that if there's enough demand for your skills, it doesn't matter how you dress (whether over or under).

There's a kind of an Overton window of dress, and one should understand what levels of dress are radical and what are acceptable at a given situation. That's why I believe people who say they "dress for themselves" are either socially maladjusted, or antisocial, or both.
I would counter that a bit with just how toxic the "brogrammer" type is, though they may be unique to my industry. Even if you like a company it's hard to avoid a few of those types getting hired, and annoyingly they will put petty nonsense like this ahead of skills.
 

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