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I dont own or have the desire to own any name brand clothes. My work clothes are definitely my most expensive, as I like to buy from bonobos (only on sale of course). For day to day, I pretty much just wear the same black pants and black tshirt, combined maybe $120. 

Ill be honest, i have never once noticed or been impressed by what someone is wearing.  

But to answer your question, a $550 suit for weddings. 

 

I have a relatively inexpensive wardrobe but I actually am impressed by people with good / expensive clothing. Provided it’s not tacky, I think it’s cool to be really well dressed.

 
ihatethefed

If shoes count, ~$400 - 450 (was a while ago so can remember exact amount) on a pair of Golden Gooses. Zero regrets - one of the best casual sneakers IMO. 

u mean golden geese?

 

I think my ski coat retails for like $750. I paid like $400 though. All of my work shirts I bought in bulk for cheap.

 

I’m kind of surprised by the comments. I’ve spent $400 on a watch (which is a lot for what is basically a piece of jewelry, but not much for a watch); $450 on an overcoat for the winter (similar amount on a parka); $850 on a suit. 
 

Those are the most expensive articles of clothing I own, but that doesn’t really strike me as crazy wasteful or anything. I don’t buy for logos, only really care about quality for the price. 

 

My wedding was a huge deal and to be honest I didn’t have to personally pay for most of it (although it still dropped six figures on it). And I felt kind of pressured / was caught up in the moment when I made the purchase.

Of course it was bespoke man, it was 10 g’s.

What made it cost so much was that it was just some high end places that claimed the material was rare and from Italy or some crap. The funny thing is that there are no logos on suits, so I can’t even show off when I wear it.

 
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My wedding was a huge deal

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"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 
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When you enter the world of luxury, I’ve found that at a certain point you just over pay for stuff.

Like wine or paintings, it’s just whatever price the market will bear.

I don’t think it was worth it, but like I said my wedding was close to 7 figures, so towards the end I was just like oh what’s another few grand. I feel like it’s the mindset of people who take out college loans, towards the end they are like oh what’s a few more grand, sure sign me up for the expensive meal plan.

Nothing about that weekend was “worth it”, but it was a fun time and a great memory.

And like I said, I only paid for about 15% myself, so who was I to tell another man how to spend his money.

The best things to spend your money on are things that provide enjoyment, but also could provide some real return - like real estate or buying a company.

Things I have wasted money on that I regret are watches, cars, clothes, super high end dinners and gambling. Things I don’t regret spending on are stocks, apartments and education.

 

I don't think any $1,000 winter coat is "worth it" on a purely functional basis but it's good quality / Goretex, I like the understated look, and I live in Toronto where it gets solid use for more than a couple of months of the year and is pretty solid down to ~ - 20C / -5F.

Array
 

~$800 on a hypebeast-type jacket (no regrets, I love wearing it and it gets compliments), 350 on common projects. Also dropped ~$1.1k on a bunch of bonobos items but none of those individually were over $100

 

I spent $800 on a Brooks Brothers suit and it fell apart. I didn't even ever get it fixed, it is in a closet somewhere. This was years ago, so probably $1000+ in today's dollars.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 
egy3gan

Wdym fell apart? What went wrong with it? just curious

The stitching on the sleeves and pants unraveled within the first month of wearing it.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

Do deal finds count? I vehnomently despise paying full price for anything, and am more than happy to wait days, weeks, or months for sale(s) on clothes, depending on selection or the in-seasonness of them. Think my best pickup was a Loro Piana Roadster Mezzocollo - retail is around $1200 AFAIK but I ended up paying a little under a third of that due to a hefty discount code, out-of-season sale, and a CC statement bonus that I used at the time. It's a great piece - wear it to work probably once a week over a button-down. I also like the sublety of it, the ordinary person would never look at it and think I'm rocking a four-figure q-zip!

 

Yeah that counts. I also look for deals, sales, etc. You can reliably get Loro Piana, Cucinelli, Tom Ford etc. at less than half of the retail price if you look hard enough (I guess it can still be expensive after discounts given the retail price can be outrageous) 

I agree on your last point although I do think people who have an eye for luxury can tell you are wearing a high quality piece of clothing.

 

Low 6 figures on a couple of watches.  

Low 4 figures on a few pairs of shoes.

Low 4 figures on a few suits.

The thing is, the 1st category doesn't really count as a "purchase" because they have only gained value since.  

 
PEarbitrage

Low 6 figures on a couple of watches.  

Low 4 figures on a few pairs of shoes.

Low 4 figures on a few suits.

The thing is, the 1st category doesn't really count as a "purchase" because they have only gained value since.  

You can certainly purchase an appreciating asset. I think you're confusing the word "purchase" with "expense." Nice purchases though. Sounds classy.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

The I have are worth it, but that has more to do with the fact that they were entirely bespoke.  I don't wear suits near as much anymore but still get use out of them.  The thing is for me bespoke is one of the only ways to get a suit that fits properly.  So that biases me in that context. 

 
egy3gan

Blizzard Rustler 9s Skis ($750)

ooo skis are clothing now? 

In that case, I have a $2000 snowboard that I got for $1000. It is a Palmer Platinum LE, a limited edition snowboard handcrafted in Switzerland by Hansjurg Kessler. I bought it to compete in Boardercross events and competed at Nationals on it at Copper Mountain, CO. Most boardercross competitors ride on Kessler designed boards. But, not all are handmade by Hansjurg Kessler. 

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

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