The School Fees We Pay - Mistakes We Make Finding Our Taste

[Sam Hober]

First off, one thing that has saved me over the past few years is that if there is any doubt in whether I really like something, then I return it. I have to actually find myself already anxiously plotting for the first chance I will have to wear this new item. If it is “okay” or “should work” then I send it back.

Here are a few “school fees” from my journey over the past few years:

Socks
This was a quick and easy lesson. I no longer own any cotton socks or any white socks. Aside from a few over the calf dress socks, all of my socks now are Darn Tough merino socks. That is way better for moisture and smell. Thick boot socks make my boots just about as comfortable as sneakers.

Sweaters/knitwear
I started off with basic Barbour knitwear, and then wanted to upgrade quality and fit. Naadam “affordable cashmere” seemed like a great idea. I liked it out of the box, but it pilled quickly and was loose. Then, I got a Johnston’s of Elgin cashmere that wears fantastically. Also, I tried Unbound merino that wears pretty well. Ultimately however, what I found is that lambswool doesn’t both my skin and is sturdier. So guess what? I took my Barbour crewnecks to the tailor and now have that perfect fit without investing in more expensive brands or fabrics.

Shoes
These fees are unavoidable. Like many, I started out with a few pairs of Allen Edmonds to get a sense of the styles I was looking for. On fit I got the 65 last in a standard 10D, as I was fitted in the store. Likely I was more of a 10E due to the narrow last.

Upon ordering Crockett & Jones, my first pair of boots was a bit loose, but I didn’t want send back due to international shipping cost. In the course of that, I acquired various sets of insoles that I experimented with, socks of different thickness, and even methods for lacing shoes. Now, I have a toolkit of different insoles and socks of different thickness where I can dial in an excellent fit on shoes up to a half size too big.

With my Crockett & Jones sizes dialed in now, it is easier to order. However, after the boots noted above, I did actually send back my next shoe order before dialing in on the perfect sizing. It was worth this cost.

Also on shoes, I bought a pair of Allen Edmonds light suede crepe sole chukkas on sale. These were probably $150 but a great bang for the buck on school fees. I learned that I can’t stand crepe soles (pick up dirt and look terrible almost immediately), don’t like chukkas (prefer either higher boots or shoes), and that the light suede color was tough to wear with anything in my wardrobe.

Buying Multiple Colors
Everyone probably does this at some point, but a few times I got a shirt in a color I liked. So then I bought a lot of colors, figuring I would wear them too. I didn’t.

Fabric Quality
These fees have been pretty unavoidable for me, but I make sure to get one item from a new brand to see how it wears and washes before buying more. Untuckit shirts are one example that did not hold up, but now I can also get a sense even on expensive brands if a fabric is not going to wear well.

Belts Don’t have to Match Shoes Exactly
In the course of ramping up my shoe collection, I gave up on this exact match concept. It is not a problem at all. Specifically, I have no desire anymore to wear a suede belt just because I have suede shoes.

Tailoring
If it is worth buying, then it is worth getting tailored to fit just right.

Also, I do not get alterations at the department store, even though they are free. One, generally I want to wash something to see if it shrinks before getting it tailored. I have tailored prematurely and ended up with something too small after a wash (tough to undo). Secondly, my tailor knows me better, and I don’t want to risk the fit with a department store tailor.

Invest in Clothing Storage
Similar to tailoring, I don’t want to invest in clothes, shoes, etc. if I will not invest in storage. Wooden hangers for shirts, butler luxury hangers for suits and jackets, rod hangers for pants, and shoulder covers for suits and jackets. Trees for shoes and boots.

If this seems expensive, I would implore you to purge your wardrobe first of the things you no longer wear.

Side note: When I have gone through and identified items to get rid of after not wearing in a year, I always try on first and think through if they go with something else. A couple of times instead of going to the donation pile, they have gone right back into my regular rotation.

Learn Your Style
Early on I got a few items that I would consider more of a preppy style. It turns out, that as I found my style those items don’t really fit right now (sorry, navy Harrington). Fortunately I did not go all in on that style, but definitely I had to pay some “school fees” to learn that about myself.

Summary Learnings
- Go slowly at first, in terms of pace of spend and cost of items. Almost all of my “first wave” items from a few years ago have left my closet. Along my style journey I realized that they either weren’t my style or fit and I got rid of them, or that they were and I have upgraded to better quality items. However, they were invaluable school fees.
- Once you start getting a sense of your style, purge liberally the stuff you won’t wear.
- Don’t keep any purchases you don’t love and can’t wait to wear. This includes fit issues.
- Invest in tailoring, storage, and maintenance.
- Find the brands that work for you.
- Figure out socks. Quality socks are a significant, but often overlooked, piece of both style and comfort.

Great post, very practical! I also have some wool socks which are comfortable but still like cotton.

 

[Bayou Tiger]

Great post, very practical! I also have some wool socks which are comfortable but still like cotton.

Thanks! How flattering to have a response from Sam Hober.

It is worth noting that I love Grenadine ties and have replaced all of my ties (excepting one sentimental tie) with Sam Hober. They are classic, stylish, and fit my overall style and persona.

 

[The Dirty Pigeon]

Some commonly shared advice in the menswear world is to "trust the tailor" when it comes to fit. While I don't disagree with this advice, completely, I have burned a lot of money over the last ten years on alterations that weren't exactly well advised. Many experienced tailors that I've visited have insisted on alterations that resulted in jackets that were too tight around the chest/waist, collar gap, trousers too slim in the legs, etc. It seems like a lot of tailors in my area are into the skinny fit style. I have been able to undo some of the bad alterations of the past and salvage some items but I've donated and started from scratch with many as well. I still occasionally have to push back on recommendations from tailors who want to make things tighter and shorter than James Bond circa 2015. Additionally, I have been surprised when tailors/suitmakers seem completely fine with fit issues that seem obvious to me. In fact, I commissioned a suit from a tailor who is highly and often recommended on this forum. Later, I posted photos to get fit feedback and there were glaring issues that users pointed out. When I went back to said tailor, he didn't seem to think that there were any problems and, dare I say, sort-of suggested that I was being a little nit-picky. Or, at least, that's how I felt. Thankfully, I didn't have to pay for that one. Anyway, I guess my point is that fully trusting your tailor and not listening to your own instincts and taste can sometimes result in exorbitant school fees.

 

[mensimageconsultant]

Some commonly shared advice in the menswear world is to "trust the tailor" when it comes to fit. While I don't disagree with this advice, completely, I have burned a lot of money over the last ten years on alterations that weren't exactly well advised. Many experienced tailors that I've visited have insisted on alterations that resulted in jackets that were too tight around the chest/waist, collar gap, trousers too slim in the legs, etc. It seems like a lot of tailors in my area are into the skinny fit style. I have been able to undo some of the bad alterations of the past and salvage some items but I've donated and started from scratch with many as well. I still occasionally have to push back on recommendations from tailors who want to make things tighter and shorter than James Bond circa 2015. Additionally, I have been surprised when tailors/suitmakers seem completely fine with fit issues that seem obvious to me. In fact, I commissioned a suit from a tailor who is highly and often recommended on this forum. Later, I posted photos to get fit feedback and there were glaring issues that users pointed out. When I went back to said tailor, he didn't seem to think that there were any problems and, dare I say, sort-of suggested that I was being a little nit-picky. Or, at least, that's how I felt. Thankfully, I didn't have to pay for that one. Anyway, I guess my point is that fully trusting your tailor and not listening to your own instincts and taste can sometimes result in exorbitant school fees.

Tailors have to make a living, and some tailors are much more technicians than artists, sometimes without a good aesthetic sense or flexibility in technique. There's an article on the site about choosing a tailor, and it probably should be expanded to address what you've noted.

 

[curtismith]

First off, one thing that has saved me over the past few years is that if there is any doubt in whether I really like something, then I return it. I have to actually find myself already anxiously plotting for the first chance I will have to wear this new item. If it is “okay” or “should work” then I send it back.

Here are a few “school fees” from my journey over the past few years:

Socks
This was a quick and easy lesson. I no longer own any cotton socks or any white socks. Aside from a few over the calf dress socks, all of my socks now are Darn Tough merino socks. That is way better for moisture and smell. Thick boot socks make my boots just about as comfortable as sneakers.

Sweaters/knitwear
I started off with basic Barbour knitwear, and then wanted to upgrade quality and fit. Naadam “affordable cashmere” seemed like a great idea. I liked it out of the box, but it pilled quickly and was loose. Then, I got a Johnston’s of Elgin cashmere that wears fantastically. Also, I tried Unbound merino that wears pretty well. Ultimately however, what I found is that lambswool doesn’t bother my skin and is sturdier. So guess what? I took my Barbour crewnecks to the tailor and now have that perfect fit without investing in more expensive brands or fabrics.

Shoes
These fees are unavoidable. Like many, I started out with a few pairs of Allen Edmonds to get a sense of the styles I was looking for. On fit I got the 65 last in a standard 10D, as I was fitted in the store. Likely I was more of a 10E due to the narrow last.

Upon ordering Crockett & Jones, my first pair of boots was a bit loose, but I didn’t want send back due to international shipping cost. In the course of that, I acquired various sets of insoles that I experimented with, socks of different thickness, and even methods for lacing shoes. Now, I have a toolkit of different insoles and socks of different thickness where I can dial in an excellent fit on shoes up to a half size too big.

With my Crockett & Jones sizes dialed in now, it is easier to order. However, after the boots noted above, I did actually send back my next shoe order before dialing in on the perfect sizing. It was worth this cost.

Also on shoes, I bought a pair of Allen Edmonds light suede crepe sole chukkas on sale. These were probably $150 but a great bang for the buck on school fees. I learned that I can’t stand crepe soles (pick up dirt and look terrible almost immediately), don’t like chukkas (prefer either higher boots or shoes), and that the light suede color was tough to wear with anything in my wardrobe.

Buying Multiple Colors
Everyone probably does this at some point, but a few times I got a shirt in a color I liked. So then I bought a lot of colors, figuring I would wear them too. I didn’t.

Fabric Quality
These fees have been pretty unavoidable for me, but I make sure to get one item from a new brand to see how it wears and washes before buying more. Untuckit shirts are one example that did not hold up, but now I can also get a sense even on expensive brands if a fabric is not going to wear well.

Belts Don’t have to Match Shoes Exactly
In the course of ramping up my shoe collection, I gave up on this exact match concept. It is not a problem at all. Specifically, I have no desire anymore to wear a suede belt just because I have suede shoes.

Tailoring
If it is worth buying, then it is worth getting tailored to fit just right.

Also, I do not get alterations at the department store, even though they are free. One, generally I want to wash something to see if it shrinks before getting it tailored. I have tailored prematurely and ended up with something too small after a wash (tough to undo). Secondly, my tailor knows me better, and I don’t want to risk the fit with a department store tailor.

Invest in Clothing Storage
Similar to tailoring, I don’t want to invest in clothes, shoes, etc. if I will not invest in storage. Wooden hangers for shirts, butler luxury hangers for suits and jackets, rod hangers for pants, and shoulder covers for suits and jackets. Trees for shoes and boots.

If this seems expensive, I would implore you to purge your wardrobe first of the things you no longer wear.

Side note: When I have gone through and identified items to get rid of after not wearing in a year, I always try on first and think through if they go with something else. A couple of times instead of going to the donation pile, they have gone right back into my regular rotation.

Learn Your Style
Early on I got a few items that I would consider more of a preppy style. It turns out, that as I found my style those items don’t really fit right now (sorry, navy Harrington). Fortunately I did not go all in on that style, but definitely I had to pay some “school fees” to learn that about myself.

Summary Learnings
- Go slowly at first, in terms of pace of spend and cost of items. Almost all of my “first wave” items from a few years ago have left my closet. Along my style journey I realized that they either weren’t my style or fit and I got rid of them, or that they were and I have upgraded to better quality items. However, they were invaluable school fees.
- Once you start getting a sense of your style, purge liberally the stuff you won’t wear.
- Don’t keep any purchases you don’t love and can’t wait to wear. This includes fit issues.
- Invest in tailoring, storage, and maintenance.
- Find the brands that work for you.
- Figure out socks. Quality socks are a significant, but often overlooked, piece of both style and comfort.

I believe in making deliberate and considered choices when it comes to shopping, rather than relying solely on the option to return items with any hint of doubt.

 

[Bayou Tiger]

I believe in making deliberate and considered choices when it comes to shopping, rather than relying solely on the option to return items with any hint of doubt.

I agree and do both. Sometimes I will narrow an entire category down to a few items to order and try. Keep rate is still less than 50%.

Fit is not 100% from online measurements and is not always correctable by a tailor.

 

[curtismith]

First off, one thing that has saved me over the past few years is that if there is any doubt in whether I really like something, then I return it. I have to actually find myself already anxiously plotting for the first chance I will have to wear this new item. If it is “okay” or “should work” then I send it back.

Here are a few “school fees” from my journey over the past few years:

Socks
This was a quick and easy lesson. I no longer own any cotton socks or any white socks. Aside from a few over the calf dress socks, all of my socks now are Darn Tough merino socks. That is way better for moisture and smell. Thick boot socks make my boots just about as comfortable as sneakers.

Sweaters/knitwear
I started off with basic Barbour knitwear, and then wanted to upgrade quality and fit. Naadam “affordable cashmere” seemed like a great idea. I liked it out of the box, but it pilled quickly and was loose. Then, I got a Johnston’s of Elgin cashmere that wears fantastically. Also, I tried Unbound merino that wears pretty well. Ultimately however, what I found is that lambswool doesn’t bother my skin and is sturdier. So guess what? I took my Barbour crewnecks to the tailor and now have that perfect fit without investing in more expensive brands or fabrics.

Shoes
These fees are unavoidable. Like many, I started out with a few pairs of Allen Edmonds to get a sense of the styles I was looking for. On fit I got the 65 last in a standard 10D, as I was fitted in the store. Likely I was more of a 10E due to the narrow last.

Upon ordering Crockett & Jones, my first pair of boots was a bit loose, but I didn’t want send back due to international shipping cost. In the course of that, I acquired various sets of insoles that I experimented with, socks of different thickness, and even methods for lacing shoes. Now, I have a toolkit of different insoles and socks of different thickness where I can dial in an excellent fit on shoes up to a half size too big.

With my Crockett & Jones sizes dialed in now, it is easier to order. However, after the boots noted above, I did actually send back my next shoe order before dialing in on the perfect sizing. It was worth this cost.

Also on shoes, I bought a pair of Allen Edmonds light suede crepe sole chukkas on sale. These were probably $150 but a great bang for the buck on school fees. Besides this I have not long ago done a writing for college referring to black lives matter with the help of here, I must say that this source really helped me a lot and I am very happy for this, moreover, I think this is a very big problem and we should attract the authorities to solve it as soon as possible. I learned that I can’t stand crepe soles (pick up dirt and look terrible almost immediately), don’t like chukkas (prefer either higher boots or shoes), and that the light suede color was tough to wear with anything in my wardrobe.

Buying Multiple Colors
Everyone probably does this at some point, but a few times I got a shirt in a color I liked. So then I bought a lot of colors, figuring I would wear them too. I didn’t.

Fabric Quality
These fees have been pretty unavoidable for me, but I make sure to get one item from a new brand to see how it wears and washes before buying more. Untuckit shirts are one example that did not hold up, but now I can also get a sense even on expensive brands if a fabric is not going to wear well.

Belts Don’t have to Match Shoes Exactly
In the course of ramping up my shoe collection, I gave up on this exact match concept. It is not a problem at all. Specifically, I have no desire anymore to wear a suede belt just because I have suede shoes.

Tailoring
If it is worth buying, then it is worth getting tailored to fit just right.

Also, I do not get alterations at the department store, even though they are free. One, generally I want to wash something to see if it shrinks before getting it tailored. I have tailored prematurely and ended up with something too small after a wash (tough to undo). Secondly, my tailor knows me better, and I don’t want to risk the fit with a department store tailor.

Invest in Clothing Storage
Similar to tailoring, I don’t want to invest in clothes, shoes, etc. if I will not invest in storage. Wooden hangers for shirts, butler luxury hangers for suits and jackets, rod hangers for pants, and shoulder covers for suits and jackets. Trees for shoes and boots.

If this seems expensive, I would implore you to purge your wardrobe first of the things you no longer wear.

Side note: When I have gone through and identified items to get rid of after not wearing in a year, I always try on first and think through if they go with something else. A couple of times instead of going to the donation pile, they have gone right back into my regular rotation.

Learn Your Style
Early on I got a few items that I would consider more of a preppy style. It turns out, that as I found my style those items don’t really fit right now (sorry, navy Harrington). Fortunately I did not go all in on that style, but definitely I had to pay some “school fees” to learn that about myself.

Summary Learnings
- Go slowly at first, in terms of pace of spend and cost of items. Almost all of my “first wave” items from a few years ago have left my closet. Along my style journey I realized that they either weren’t my style or fit and I got rid of them, or that they were and I have upgraded to better quality items. However, they were invaluable school fees.
- Once you start getting a sense of your style, purge liberally the stuff you won’t wear.
- Don’t keep any purchases you don’t love and can’t wait to wear. This includes fit issues.
- Invest in tailoring, storage, and maintenance.
- Find the brands that work for you.
- Figure out socks. Quality socks are a significant, but often overlooked, piece of both style and comfort.

I agree and do both. Sometimes I will narrow an entire category down to a few items to order and try. Keep rate is still less than 50%.

Fit is not 100% from online measurements and is not always correctable by a tailor.

That's fine, but about 50% is strange

 

[DapperPhilly]

That's fine, but about 50% is strange

Not strange at all

 

[William Kazak]

Very interesting comments here. I have made my share of paying school fees. Ferragamo shoes. I gave away that pair to a Greek friend. Cowboy boots. That heel was ridiculous to walk on. RL Olympics blazer online at eBay. Too tight. After all, it is made for an athlete! Shirts without exact sleeve lengths. 17 1/2 34. Not 34/35. White bucks a half size too tight. Thinking of keeping but I already have Church's white bucks wingtips. I finally realized that light pink shirts as found in men's dress shirts are too pale for my blonde complexion. I need colors that are rich. Studied Seasonal Color Analysis books and realized finally what colors work for me (spring). Not summer which is very light pastels. Those bottomless blue/black looking blazers are too dark for me. But, I still keep two around. One has the brass nautical buttons. The other has double vents in the rear. Found them at Goodwill. They were custom made who is probable gone by now. Too tight Lora Piana Camelhair topcoat at Goodwill. Gave it to a friend and bought myself a BB version that fits with a sweater. I realized that I like lambswool crew necks for winter and Shetland crews. I live in Illinois and it gets cold. I do not wear shirts under a crew neck I wear long sleeved t - shirts. I love LR pleated and cuffed trousers. Thank you LE. I just ordered an Orvis Urinate Kakis from eBay to see if I like the brand since I just found out LE is not stocking my chinos now. Some wasted spending. Still kicking!

 

[Mirage-]

Some commonly shared advice in the menswear world is to "trust the tailor" when it comes to fit. While I don't disagree with this advice, completely, I have burned a lot of money over the last ten years on alterations that weren't exactly well advised. Many experienced tailors that I've visited have insisted on alterations that resulted in jackets that were too tight around the chest/waist, collar gap, trousers too slim in the legs, etc. It seems like a lot of tailors in my area are into the skinny fit style. I have been able to undo some of the bad alterations of the past and salvage some items but I've donated and started from scratch with many as well. I still occasionally have to push back on recommendations from tailors who want to make things tighter and shorter than James Bond circa 2015. Additionally, I have been surprised when tailors/suitmakers seem completely fine with fit issues that seem obvious to me. In fact, I commissioned a suit from a tailor who is highly and often recommended on this forum. Later, I posted photos to get fit feedback and there were glaring issues that users pointed out. When I went back to said tailor, he didn't seem to think that there were any problems and, dare I say, sort-of suggested that I was being a little nit-picky. Or, at least, that's how I felt. Thankfully, I didn't have to pay for that one. Anyway, I guess my point is that fully trusting your tailor and not listening to your own instincts and taste can sometimes result in exorbitant school fees.

Ironically my experience with local alteration tailors is that they generally want to hem my trousers way too long (half or even full break, with cuffed trousers, while I ask for quarter break), with a cuff that is too short (often 3cm, I insist for 4 - I know 5 is standard here but I'm short), and yet suggest a leg that is too trim (very tapered like nearly all Italian trousers, rather than straight).
This boggles my mind: the trimmer they are, the shorter they have to be in order not to puddle on your shoes. Which is another reason (beyond keeping proportion with jackets) why I really want straight trousers, since I don't want to have to wear them at half ankle like the stereotypical SS model in order to get a clear uninterrupted leg line.
Even assuming they had their own aesthetic in mind, which I unfortunately don't think they do, how do they not get that they are trying to push me in conflicting directions?

 

[William Kazak]

Very interesting comments here. I have made my share of paying school fees. Ferragamo shoes. I gave away that pair to a Greek friend. Cowboy boots. That heel was ridiculous to walk on. RL Olympics blazer online at eBay. Too tight. After all, it is made for an athlete! Shirts without exact sleeve lengths. 17 1/2 34. Not 34/35. White bucks a half size too tight. Thinking of keeping but I already have Church's white bucks wingtips. I finally realized that light pink shirts as found in men's dress shirts are too pale for my blonde complexion. I need colors that are rich. Studied Seasonal Color Analysis books and realized finally what colors work for me (spring). Not summer which is very light pastels. Those bottomless blue/black looking blazers are too dark for me. But, I still keep two around. One has the brass nautical buttons. The other has double vents in the rear. Found them at Goodwill. They were custom made who is probable gone by now. Too tight Lora Piana Camelhair topcoat at Goodwill. Gave it to a friend and bought myself a BB version that fits with a sweater. I realized that I like lambswool crew necks for winter and Shetland crews. I live in Illinois and it gets cold. I do not wear shirts under a crew neck I wear long sleeved t - shirts. I love LR pleated and cuffed trousers. Thank you LE. I just ordered an Orvis Urinate Kakis from eBay to see if I like the brand since I just found out LE is not stocking my chinos now. Some wasted spending. Still kicking!

Orvis Ultimate Kakis, that I am waiting for.

 

[NadalRG]

This is probably where I paid my heaviest fees. In the beginning I spent quite a bit of money on CM, grey trousers and blue blazers and navy suits and black oxfords (granted most of these were on sale or thrift finds). I ended up spending a large amount of time trying to find places I could wear my clothes and not look so out of place. No one wears grey trousers and a blue blazer where I live.

Tell me about it. I live in Miami and people dress like absolute bums here, plus the weather does not help being very hot and humid almost all year round.

 

[Testudo_Aubreii]

Never visited Miami, but for tropical beach weather, I do MTM guayaberas and linen trousers. I like the Yucatan-style ones with the rib pleats (alforzas). But only in 100% linen. The Cuban four-pocket ones also work well, if you can get the shape right (they can easily look quite boxy). Those are basically the same as a safari shirt.

Tell me about it. I live in Miami and people dress like absolute bums here, plus the weather does not help being very hot and humid almost all year round.

 

[FlyingMonkey]

Most of the mistakes I've made were secondhand purchases so I didn't lose much by them, and even had a bit of a laugh. I don't regret my foray into bespoke because I kept and still wear everything I commissioned once in a while, but generally speaking I just wear what I find interesting these days. Most of it is not what this side of the forum would see as being well-dressed, although I have a very carefully selected wardrobe that allows me to dress appropriately for virtually any occasion I'm likely to encounter. I know what I am doing, and I'm happy.

 

[bjornb17]

This thread is sort of like AA but for clothing enthusiasts. So with that said, hello, I am bjornb17.

I was referred to this thread based on my comment on another thread. Below is my comment but expanded upon for this thread:

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. And I wonder how it will be in 5 years looking back to this day. 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. I feel like I am sort of a filter, buying a lot of things that I think I like, keeping the things I love, and pretty quickly selling off the things that aren't quite working for me. My current wardrobe is like the all star game of my favorite things over the years and now I'm super excited to wear everything I have.

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, and best of all they fit amazing in the larger size. I made the right call in reordering. 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 and I feel a lot more confident in them. They are totally "me" whereas the first iterations were for somebody I was pretending to be, if that makes sense. 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. Also since my new batch of shirts are so perfect for me, I sell most of my older inventory since they don't live up to my current evolved standard.

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. Buying stuff, receiving it, trying it, and then sometimes having to get rid of it is kind of fun in its own way.

Initially I felt kind of stupid for the money wasted, but after reading through this thread I understand it is a common and probably important part of the process. The biggest lesson I learned is to be a bit less impulsive and more selective when buying new things, but it is okay to try things, make mistakes and learn from them.