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How to cope with losing money with constant style mistakes when learning?

bjornb17

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I've been on this sartorial journey for about 14 years now. They say it is about the journey, not the destination, and that is so true since my style and knowledge is ever-evolving. I figured by now I would have things more or less dialed in, but it is a constant process. When I look at my sense of style now versus even just a few years ago, I'm surprised by how far I've come - despite my style more or less being the same or similar, the fit, details, and ability to pull off an outfit confidently has gotten way better. But, it all comes at a cost as I buy stuff, try it, find out what works and doesn't work, and then sell a good portion of it at a loss.

One example is my shoe game. I've worn Allen Edmonds for a number of years and they were satisfactory, but, there was always something missing in my eyes. They styles were a little too conservative, the detailing was a little too sloppy, none of the lasts or sizes ever seem to fit me quite right, etc. Enter Carmina and their custom shoe configuration. For $685 you can get exactly the shoe you want! For about double or triple the price of what you would normally pay for Allen Edmonds. I visit several menswear outfitters and get a second and third opinion on my shoe size and do meticulous research here and elsewhere on how to expect the new shoes to fit. I order two pairs for nearly $1400 and wait 2 months. I get them and they are gorgeous, but oops! I really should have ordered a half size larger. I re-order the two pairs again for $1400 and then sell my two pairs of shoes in the wrong size for approximately $900. I lost $500 in the process but now my shoe game is significantly elevated and I love my new Carmina shoes way more than any AE I've ever laid eyes on. Lesson learned and for future orders I now have my size and last dialed in perfectly. I'm always excited to wear my Carminas and couldn't be happier.

Next example - custom shirts. I'm currently trying to elevate my shirt game. After all these years I finally have my shirt measurements dialed in just the way I like it, but I'm feeling experimental. I order a handful of shirts with details I've always sought after like extreme cutaway collars, mitered french cuffs, etc. A few weeks later I get my new shirts that I spent a lot of money on. They are gorgeous. Except one thing, that collar and cuff combo just looks a little bit too over the top on me and doesn't flatter my physique as much. I reorder a few shirts this time with a medium spread collar and square french cuffs, in the same patterns, and they look 100% better on me. They are a bit more understated but look really sharp. I sell the first batch of shirts on ebay for about 50% of what I paid for them. The buyers are happy and I'm happy to get them out of my closet, but I lost some money in the process. However, again, I learned a few things and my shirt game has been elevated a bit from where it was and now I'm happy with the knowledge of what looks good on me and what doesn't.

Same example goes for suits or any other menswear topic you can think of.

In the end I learned a lot, mostly had fun, look better, but I lost a moderate chunk of money in the the process. I earn enough money that this does not adversely impact be financially, but I can't help but feel slightly guilty at the thought of being financially inefficient, but I'm also pleased with the evolution of my style and what I've learned along the way. Am I actually being stupid with how I'm approaching this, or is that just the cost of learning something?
 

breakaway01

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No -- you are certainly not alone in this.
A good thread to peruse
 

bjornb17

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No -- you are certainly not alone in this.
A good thread to peruse

Thanks for the link that was a great read! Not only am I not alone, I think I've probably lost less money paying dues than most of the commenters (so far, at least haha).
 

wolfdale

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I am only at the start of my sartorial journey but reading this post has been very reassuring. Thank you for taking the time to write!
 

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