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Totally relative to income and spending habits. A $100 suit might be really expensive for someone who has to work days for that $100. A person with high income but hates spending money might see a $500 suit as expensive even though they can easily afford it. A billionaire might see a $3K suit as budget if the suits they usually buy cost $5K.
 
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I’m not sure I understand the question. What kind of clothing are you talking about? Casual, formal?

Cost and one’s definition of “expensive” is all relative. For example can spend $10 on a shirt, or $50, or $150, or $500+.
 
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I'm short and not remotely slim and, in recent years, I have worked in positions where well-cut, sober garments best met my professional needs.

These days, I get my jackets, suits and trousers made to measure, in other words, I mostly wear bespoke tailoring.

Now, I will admit that I have always liked good tailoring, and, even in my teaching days, I wore well cut tweed and wool garments, good commercial brands, such as the German company, Gardeur. So, even twenty years ago, my suits cost a few hundred pounds, euros, as did my jackets, and trousers.

But, they drape properly on me, and fit well.

My shoes are almost all by Church's, and I get them made to measure, and then resoled as needed.

I will add that the tyranny of fashion (this size zero nonsense) plus the current preferences for fitted garments, means that it is difficult for someone such as myself, who insists on good quality natural fibres, to find something comfortable, (not tight), that fits and sits right on my build.
 
Wearing expensive brands does not necessarily make one a stylish person. Style is about finding what works for you and your own particular point of view.

I do like nice clothes that are well-tailored, and I always somewhat overdressed for working in creative / tech industries, but in the wake of the pandemic and the rise of remote work, there's just no reason for me to invest in dress shoes or nice slacks or whatever.

Four years on, and looser clothing has come back in style again. I bought some "standard cut" jeans recently and they feel positively billowy compared to my regular slim fits, but I'll probably get used to it. With menswear, at least what's fashionable doesn't change so rapidly.
 
Wearing expensive brands does not necessarily make one a stylish person. Style is about finding what works for you and your own particular point of view.
The older I get the more I dress and look like a homeless person :)

I recall going to a wedding recently, and my wife was a mad at me, because I was wearing sneakers with my suit. I told her at my age, the comfort of my feet trumps any sort of social convention of what footwear is appropriate.

Edit: So it seems someone here cares about how I dress :p
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Since I was a kid my mother purchased high end second hand clothes from a longtime local shop. I too acquired many fine jackets, suits, shirts, pants, etc. from there over the years (even a tuxedo that I still wear to black tie occasions). Don't put them on as often these days as work went casual a decade ago.

I've purchased new and second hand shoes that are 20+ years old now (Clark's and Mephisto's) that are still going strong after a couple of factory resole "tours".
 
The older I get the more I dress and look like a homeless person :)
This is me. I started WFH as soon as California closed down (March 18, 2020). Started out normal: wake up, shower, dress then into my home office (in my garage) for 12 hours of work. It actually took me a few months to realize I now could wear shorts for work in summer (or any other time I want, other than going out of the house for whatever, I now almost never wear pants).

Fast forward a couple of years and I wear very comfortable clothes, shoes and even wear my robe if chilly in the morning.

I also last had my hair cut sometime last year when things started to open up, but now have fallen back on my 60's-70's childhood and have a ponytail. I haven't had long hair since high school.

Last item, we are on a 4-year-old thread, I hope he figured out his fashion issues.
 
Fast forward a couple of years and I wear very comfortable clothes, shoes and even wear my robe if chilly in the morning.
Exactly, If I'm working from home, going out food shopping, or just doing errands, I want to be comfortable, and just do my own thing. I'm not hurting anyone and life is too short to be doing something just to fit in to some sort of artificial construct of what to wear :)
 
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The trick is to find a style that works well for you, and is comfortable, and - if necessary, or, if this is what you want - also stylish.

Find what looks well and works well on you, rather than succumbing to the ephemeral whims of what is considered to be fashionable.
 
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