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

[JohnMRobie]

Recently Derek Guy posted a series of articles on how to go about developing good taste featuring a few guys I have on my short list that I follow and think are exceptionally well dressed but also very knowledgeable.

In Mark Cho’s essay one of the things mentioned was the concept of paying school fees on our path to developing our taste and sense of style - The purchases that don’t work out for any number of reasons whether it’s fit, a piece of clothing that ends up being dated from the peak #menswear era, or just changing preferences. It seems like we don’t discuss these things on here often. The mistakes get glossed over in exchange for opportunities to flex with our new jawnz.

While we can certainly develop good taste as DWW’s essay posits, I think it’s equally important to find our voice and it’s hard to do these things without making purchases and making mistakes. I’ve often bemoaned the fact that I made mistakes and if I could have just started where I am now I would have saved an awful lot of money but the reality is I would have still made mistakes, they just would have been more expensive mistakes.

I have no idea if this will interest anyone else but here it is. A thread for our mistakes and for our reality checks. A place we can all realize we are human, not every fit is a winner and the new guy can find out he’s not the first one to throw together an outfit that just didn’t work. That sometimes we buy things that don’t fit well and maybe even age worse.

 

[FlyingHorker]

Spoiler: Slim overcoats/topcoats

Buying a trim topcoat/overcoat. I know many here still dig this look, but I outgrew this thing in 3 years, and the back sucked from the get-go.

For now (now meaning who knows how my taste will change again), I've moved onto enormous coats that are 1-2 sizes too large for me, and I prefer the comfort and look. I can actually layer, and I notice I'm much warmer with lighter weight fabrics. Now I get what people meant by having an actual layer of insulation between you and your coats.

I'm sure I look like a kid wearing his dad's clothes to many people, but I dig it.

Spoiler: Emerald green trousers in worsted wool

I had these made by my tailor so I could wear them with just a shirt during summer time. I can't do tailoring from June-August, so I wanted pants that could do more "lifting" without a jacket. The end result was something that works with nothing. I kept them for future fittings with my tailor, and that one is to be continued with my latest project. So not a total waste.

CM's central look is a tailored jacket. When that can't be worn, move onto a different look IMO.

Lately I've chosen baggy camp collar printed shirts paired with baggy fatigue pants. It's overall a wider look, is comfortable, and has airflow. It's completely shapeless, but I'm ok with that

 

[Sreezy36]

Mistake Number 1 on my journey
raw Demim. I have spent thousands of dollars and tried numerous brands. I still haven’t found the right fit. I’ve come to the conclusion that they aren’t for me.

 

[JohnMRobie]

After about a decade and a half of being a CM guy lord knows I’ve made my fair share of trips to Goodwill to offload that purchase that I thought was going to be sweet.

There are the obvious ones the Gucci, Ferragamo and Santoni shoe purchases - Especially those beautiful walnut orange corrected grain shade double monks in 2009 or so. The mid-blue suit with the narrow lapels and cigarette leg trousers. The cropped jackets. The MTM experiment where the advisor insisted on the contrast button holes.

But I think more informative and more interesting are the things that should have worked and should have been timeless and would likely be defined as being in good taste from an aesthetic standpoint. A lot of these purchases I frankly think were informed by lists. There’s a value to some of those, the 5 suits you need, 5 pairs of shoes, etc. but by sticking to the lists I paid a lot of school fees. Others have written here before about how lists can push us to buy things we don’t need. Looking back I believe this to be the case for myself.

Things that come to mind are split toe derby’s that ended up never feeling quite right to wear with my taste and choices as they settled into where they were going even though I fully understand the versatility argument but they just rarely got worn. I tried to force it. That first pair didn’t work? I better try [insert upgraded brand.] Maybe a different color. Turns out they just never spoke to me and never felt right. The same goes for various color combinations and learning what I felt most comfortable in and what got worn most often.

I have to say I’ve had more fun in this hobby purging things and saying lists be damned, this is what I wear and I wear it often and actually enjoying my clothes. The refining. Getting rid of the clutter. The things that checked a box and collected dust. I still have more things than I know what to do with but they get used. Everything has its role and has its place. Nobody in their right mind would have recommended that I build my wardrobe with what I ended up with. It would be viewed as duplicative, missing key elements, etc. but after paying all those school fees I feel like I’ve found what works for me (until that inevitably changes and I get to redo this process again)

 

[JFWR]

This is an interesting thread. Sadly, I don't have a lot of these stories as I tried to pick decent clothing right from the get go, and as a result except for the things I had to retire due to wear and tear, I don't really think I have any clothes that I just don't wear. I might not wear them in the same combinations, as I have certainly tried to do some stuff that just didn't work, but I mean the clothes I have are generally clothes I still wear. I'm satisfied with how I look.

In contrast, I used to wear some absolutely crap shoes. Not only were they crappily made and look crappy, but they felt crappy. I just didn't realize that going for quality mattered for comfort as well as style.

Before these shoes became my official "go to the garbage bin out back" shoes, I used to wear these (polished up with laces, mind you) to work and out and such. I am embarrassed to post these, but check 'em out:



Worse, I actually had three pairs of these. Two in black, one in brown. I wore these shoes almost exclusively for like, 2-3 years, too. I want to punch myself in the face for this fashion AND comfort choice.

 

[JohnMRobie]

I’ll try to clarify my thoughts here - Certainly quality can be a part of it and upgrading to better things. Some mistakes can be avoided by purchasing decent quality things. But the more interesting part is developing your style, your taste.

An excerpt from Mark’s essay here (edited for length. Read the full version at DWW’s site)

Beyond simply looking at things, I believe it is even more important to fully experience them. When it comes to clothes (and even watches), this entails trying them on and, ideally, owning them for a while…. If the purchase works out, that’s fantastic; if it doesn’t, don’t let it bother you. There’s a Chinese phrase for when you lose money on something that translates to “paying school fees.” I’ve paid a lot of school fees, and I don’t consider any of it wasted money. Even through the mistakes, I’ve learned a lot. It’s nearly impossible to know if you will like something until you own it. Accept that your preferences will shift. Nothing is eternal. That Royal Oak that everyone seems to want will most likely not hold their interest ten years from now. Today’s perfect navy blazer may require an update later. It’s OK! Accept your changes and use them to broaden and develop your palate. If you’ve been paying attention from the beginning, you’ll make even better decisions in the future.

I think the above brings up an interesting sort of dilemma. Is it truly possible to develop your taste and learn what works for you without making mistakes? I’d argue it is not but instead of sweeping the mistakes under the rug or suppressing the memories I’m curious how they impacted the choices we make.

 

[JFWR]

I’ll try to clarify my thoughts here - Certainly quality can be a part of it and upgrading to better things. Some mistakes can be avoided by purchasing decent quality things. But the more interesting part is developing your style, your taste.

An excerpt from Mark’s essay here (edited for length. Read the full version at DWW’s site)



I think the above brings up an interesting sort of dilemma. Is it truly possible to develop your taste and learn what works for you without making mistakes? I’d argue it is not but instead of sweeping the mistakes under the rug or suppressing the memories I’m curious how they impacted the choices we make.

I imagine some people do luck into taste by just having an innate sense of style and the like right from the get go.

Most of us, though, I imagine are firmly in the boat of having made a number of mistakes, or at least, having walked something of a road to get there. There's definitely been a "style journey" for myself, but it is more like refining what I already enjoyed or adding in new bits that were wanting.

The one thing I can say for myself, though, is I just never made extravagant purchases that I just came to later despise. Or if I did, I despised them quick enough to return them. They were tried on, found wanting, and shipped back. Conversely, if they were thrifted, I probably don't even remember giving them back to charity. They were never in my life for long enough for me to really consider them "mine".

I suppose having a more limited budget than some men here has saved me from falling victim to various traps.

I actually worry as I grow in my career and disposable income that I will fall victim to such mistakes more often. One thing I am on the look out is "don't buy beautiful things you can't possibly have a reason to wear or use".

 

[GaiusM]

I jumped into an MTM jacket way too soon, before I had enough experience wearing jackets to know what I wanted and the subtle differences in fit and feel. I was not able to communicate clearly enough with the tailor to really nail the fit and chose him rather hastily to start with. The end result wasn't terrible but was a disappointing and expensive experience, especially when I found an RTW jacket in the same fabric just a few months later for a fraction of the price that fit better.

Learning to truly understand proper fit has also led to dues paid. I can't recall how many pairs of trousers, chinos and other bottoms I've had to get rid of due to the Athlete's Curse of big thighs and butt. Add in the extra costs of taking in waists that are 1 or 2 sizes too big but finally fit in the legs as well.

To go with the above stylistically what looks great on the 183cm 74kg model swimming in size M looks awful on me at 180cm 90kg stuffed into size XL. It took a while, and a lot of erroneous purchases, to begin to figure out what works with my body composition and frame (special thanks to pleats).

 

[bicycleradical]

I became interested in CM styles about a decade ago, when approaching middle age and coming to terms with the idea that I had to present myself to the world better than I was doing. In my haste, I got pretty excited and bought far too many oxfords. In retrospect, it would have been better to buy more derbies and loafers to have some variety with my shoes however I still wear them and enjoy them.

 

[7_rocket]

Biggest mistake I made was buying things with no context. I read way too much into CM section of this forum. Instead of buying clothing/footwear based on what I did for a living, my lifestyle and places, I frequented.

I bought into the "essentials" "wardrobe basics" etc. Tried to convince myself that I "needed" oxford shoes or 3 different shades of grey pants.

You live and you learn

 

[Blastwice]

I spent on brands and RTW only to discover a tailor, a shoemaker, and small ateliers are the way to go if you want to truly feel like all the pieces fit together.

Once you work with people who know what they are doing and have access to the right raw materials, the sky is truly the limit and fashion becomes a game you cannot lose.

 

[JohnMRobie]

I imagine some people do luck into taste by just having an innate sense of style and the like right from the get go.

Most of us, though, I imagine are firmly in the boat of having made a number of mistakes, or at least, having walked something of a road to get there. There's definitely been a "style journey" for myself, but it is more like refining what I already enjoyed or adding in new bits that were wanting.

The one thing I can say for myself, though, is I just never made extravagant purchases that I just came to later despise. Or if I did, I despised them quick enough to return them. They were tried on, found wanting, and shipped back. Conversely, if they were thrifted, I probably don't even remember giving them back to charity. They were never in my life for long enough for me to really consider them "mine".

I suppose having a more limited budget than some men here has saved me from falling victim to various traps.

I actually worry as I grow in my career and disposable income that I will fall victim to such mistakes more often. One thing I am on the look out is "don't buy beautiful things you can't possibly have a reason to wear or use".

You hit on a few things that I think provide an interesting lens. Caveat here: None of what I am trying to say is that you must be a bespoke customer to dress well or dress in good taste but I’m going to use some examples to visualize it. Thankfully there are plentiful options that have emerged recently to make these things more accessible.

I believe there is a distinction between dressing well in things that fit and finding your style. I also don’t think any of these things are mutually exclusive. It’s possible to dress well without finding your own style - A good tailor or shoemaker, knowledgeable sales associate or guide can help with this by purely sticking to rules.

It’s also possible to dress poorly while finding your style and being honest to your voice. It’s possible to do both without wearing what would be considered SF CM approved “good taste” but that’s a different debate for a different day.

To your post the first thing you hit on is resources. It can absolutely be more difficult to determine some of the details and learn how they look on you and how you like them. Particularly those details which are not readily available as RTW (though this has gotten better.) This is certainly relatable.

When I first started I was limited by what was around me. Off the rack tailoring. And if we are being honest, mid-late 00’s tailoring from

Spoiler: Canali

and

Spoiler: Zegna

were fairly uninspired and generic. A couple examples I still have in my closet so not school fees per se. RTW also tends to focus on softer, light weight cloths.

There was little to no learning about how different silhouettes and details fit and look with your body when wearing generic RTW tailoring in that era even though they generally fit ok and wouldn’t be considered bad taste IMO. Same goes with cloth that is light and doesn’t drape particularly well.

The other is a related but different. It’s simply the level which any of us care about any of these things but to do so, school fees must be paid. Finding out if an extended shoulder is a better choice for you. Should you go for a Scholte Drape? Is lean and clean more to your preference? Con rollino? Spalla camicia? A more closed or open quarters? Does the rounded softness of a Florentine jacket work on your frame or does it just make you look like a bowling ball? What about built up shoulders and a house with a more military inspired style?

If you’ve spent some time on Simon’s site he has tried tailors from around the world. From

Spoiler: Chittleborough and Morgan

to

Spoiler: Panico

Each looks slightly different. Note the shoulders in particular. Are they each in good taste? Certainly. Do they all fit? Most of them. But the silhouette and details are slightly different on each. They accentuate certain features of his. I haven’t any clue which he thinks is most his style. Perhaps for him his authentic voice is “guy who samples bespoke tailors.”

Is it possible to look put together without going through that process? Certainly. Is it possible to find what works best for you or find your style and voice? I think less so. To develop one’s own taste and style I think a certain level of experimentation, risk and investment must be made to answer the above. We just don’t know what we don’t know and until we try it, wear it and live in it can we know?

 

[comrade]

I have been very lucky in being much older than most of the posters.
I was always interested in clothes beginning with cowboy and/or soldier
costumes when I was about 4. I came of age during the Ivy heyday so
there was a style that was prevalent among East Coast upper middle
class elite college-bound snobs like myself that I could adapt. Naturally,
I wound up at an Ivy League college which further reenforced my style
choices. And perhaps most importantly, my Dad dressed in an understated
tweedy "trad" style in contrast with most of his friends and other adult family
members. After college my personal taste evolved to favoring more shaped
jackets, often with side vents in imitation of British style, but always with
natural shoulders. This style, looks better on my build, than the sack suits
I used to wear. In the 80s and 90s I wore mostly a Chipp model that was more
shaped along with Norman Hilton and PaulStuart. More recently, it has been
Belvest, Isaia, Partenopea, H Freeman and Rubinacci. None are short or
slim fitted. I live in the SF Bay Area where the selection for clothes in my
taste is abysmal, so I take my chances with the internet. Since I have little
need for tailored clothing, I buy it as more of a hobby and cannot justify the
expense and long process of visiting tailor Bespoke.

 

[JFWR]

You hit on a few things that I think provide an interesting lens. Caveat here: None of what I am trying to say is that you must be a bespoke customer to dress well or dress in good taste but I’m going to use some examples to visualize it. Thankfully there are plentiful options that have emerged recently to make these things more accessible.

I believe there is a distinction between dressing well in things that fit and finding your style. I also don’t think any of these things are mutually exclusive. It’s possible to dress well without finding your own style - A good tailor or shoemaker, knowledgeable sales associate or guide can help with this by purely sticking to rules.

Good point. It is possible to dress well just by sort of fitting into the groove of an established style and having knowledgeable enough people to point out when something just doesn't fit.. Although I think the fear here is that you can end up just utterly indistinguishable from everyone else if you fall into that niche uncritically, and therefore risk mediocrity. How many lawyers, bankers, etc, are dressed well, but look completely drone-ish, for instance? They lack style, even if they are well put together.

It’s also possible to dress poorly while finding your style and being honest to your voice. It’s possible to do both without wearing what would be considered SF CM approved “good taste” but that’s a different debate for a different day.

To your post the first thing you hit on is resources. It can absolutely be more difficult to determine some of the details and learn how they look on you and how you like them. Particularly those details which are not readily available as RTW (though this has gotten better.) This is certainly relatable.

When I first started I was limited by what was around me. Off the rack tailoring. And if we are being honest, mid-late 00’s tailoring from

Spoiler: Canali

View attachment 1845805

and

Spoiler: Zegna

View attachment 1845804

were fairly uninspired and generic. A couple examples I still have in my closet so not school fees per se. RTW also tends to focus on softer, light weight cloths.

There was little to no learning about how different silhouettes and details fit and look with your body when wearing generic RTW tailoring in that era even though they generally fit ok and wouldn’t be considered bad taste IMO. Same goes with cloth that is light and doesn’t drape particularly well.

The other is a related but different. It’s simply the level which any of us care about any of these things but to do so, school fees must be paid. Finding out if an extended shoulder is a better choice for you. Should you go for a Scholte Drape? Is lean and clean more to your preference? Con rollino? Spalla camicia? A more closed or open quarters? Does the rounded softness of a Florentine jacket work on your frame or does it just make you look like a bowling ball? What about built up shoulders and a house with a more military inspired style?

If you’ve spent some time on Simon’s site he has tried tailors from around the world. From

Spoiler: Chittleborough and Morgan

View attachment 1845810

to

Spoiler: Panico

View attachment 1845812

Each looks slightly different. Note the shoulders in particular. Are they each in good taste? Certainly. Do they all fit? Most of them. But the silhouette and details are slightly different on each. They accentuate certain features of his. I haven’t any clue which he thinks is most his style. Perhaps for him his authentic voice is “guy who samples bespoke tailors.”

Is it possible to look put together without going through that process? Certainly. Is it possible to find what works best for you or find your style and voice? I think less so. To develop one’s own taste and style I think a certain level of experimentation, risk and investment must be made to answer the above. We just don’t know what we don’t know and until we try it, wear it and live in it can we know?

I think you are right that the extent of finding what works requires failures on that road.

Or rather, let's say this: It is possible to be locked into a look that you like, that fits, etc, but never having adventured beyond that point and as a result, you might not have expanded your options as fully as you might have.

I think your examples from Simon is a good example.

Suppose a man were to have just stuck with picture #1. He'd be well dressed and it would fit well, but he never would have also experienced the other side of things which are equally well put together, but a different look.

Reflecting on my style journey, I imagine that I just haven't expanded all my options yet. I frankly don't have the resources to sample multiple different bespoke tailors, so doing something like Simon does is just something I can't manage to do right now.

 

[comrade]

You hit on a few things that I think provide an interesting lens. Caveat here: None of what I am trying to say is that you must be a bespoke customer to dress well or dress in good taste but I’m going to use some examples to visualize it. Thankfully there are plentiful options that have emerged recently to make these things more accessible.

I believe there is a distinction between dressing well in things that fit and finding your style. I also don’t think any of these things are mutually exclusive. It’s possible to dress well without finding your own style - A good tailor or shoemaker, knowledgeable sales associate or guide can help with this by purely sticking to rules.

It’s also possible to dress poorly while finding your style and being honest to your voice. It’s possible to do both without wearing what would be considered SF CM approved “good taste” but that’s a different debate for a different day.

To your post the first thing you hit on is resources. It can absolutely be more difficult to determine some of the details and learn how they look on you and how you like them. Particularly those details which are not readily available as RTW (though this has gotten better.) This is certainly relatable.

When I first started I was limited by what was around me. Off the rack tailoring. And if we are being honest, mid-late 00’s tailoring from

Spoiler: Canali

View attachment 1845805

and

Spoiler: Zegna

View attachment 1845804

were fairly uninspired and generic. A couple examples I still have in my closet so not school fees per se. RTW also tends to focus on softer, light weight cloths.

There was little to no learning about how different silhouettes and details fit and look with your body when wearing generic RTW tailoring in that era even though they generally fit ok and wouldn’t be considered bad taste IMO. Same goes with cloth that is light and doesn’t drape particularly well.

The other is a related but different. It’s simply the level which any of us care about any of these things but to do so, school fees must be paid. Finding out if an extended shoulder is a better choice for you. Should you go for a Scholte Drape? Is lean and clean more to your preference? Con rollino? Spalla camicia? A more closed or open quarters? Does the rounded softness of a Florentine jacket work on your frame or does it just make you look like a bowling ball? What about built up shoulders and a house with a more military inspired style?

If you’ve spent some time on Simon’s site he has tried tailors from around the world. From

Spoiler: Chittleborough and Morgan

View attachment 1845810

to

Spoiler: Panico

View attachment 1845812

Each looks slightly different. Note the shoulders in particular. Are they each in good taste? Certainly. Do they all fit? Most of them. But the silhouette and details are slightly different on each. They accentuate certain features of his. I haven’t any clue which he thinks is most his style. Perhaps for him his authentic voice is “guy who samples bespoke tailors.”

You hit on a few things that I think provide an interesting lens. Caveat here: None of what I am trying to say is that you must be a bespoke customer to dress well or dress in good taste but I’m going to use some examples to visualize it. Thankfully there are plentiful options that have emerged recently to make these things more accessible.

I believe there is a distinction between dressing well in things that fit and finding your style. I also don’t think any of these things are mutually exclusive. It’s possible to dress well without finding your own style - A good tailor or shoemaker, knowledgeable sales associate or guide can help with this by purely sticking to rules.

It’s also possible to dress poorly while finding your style and being honest to your voice. It’s possible to do both without wearing what would be considered SF CM approved “good taste” but that’s a different debate for a different day.

To your post the first thing you hit on is resources. It can absolutely be more difficult to determine some of the details and learn how they look on you and how you like them. Particularly those details which are not readily available as RTW (though this has gotten better.) This is certainly relatable.

When I first started I was limited by what was around me. Off the rack tailoring. And if we are being honest, mid-late 00’s tailoring from

Spoiler: Canali

View attachment 1845805

and

Spoiler: Zegna

View attachment 1845804

were fairly uninspired and generic. A couple examples I still have in my closet so not school fees per se. RTW also tends to focus on softer, light weight cloths.

There was little to no learning about how different silhouettes and details fit and look with your body when wearing generic RTW tailoring in that era even though they generally fit ok and wouldn’t be considered bad taste IMO. Same goes with cloth that is light and doesn’t drape particularly well.

The other is a related but different. It’s simply the level which any of us care about any of these things but to do so, school fees must be paid. Finding out if an extended shoulder is a better choice for you. Should you go for a Scholte Drape? Is lean and clean more to your preference? Con rollino? Spalla camicia? A more closed or open quarters? Does the rounded softness of a Florentine jacket work on your frame or does it just make you look like a bowling ball? What about built up shoulders and a house with a more military inspired style?

If you’ve spent some time on Simon’s site he has tried tailors from around the world. From

Spoiler: Chittleborough and Morgan

View attachment 1845810

to

Spoiler: Panico

View attachment 1845812

Each looks slightly different. Note the shoulders in particular.

Simon has very sloped shoulders, which if I recall correctly,
he has noted himself. He is also tall and lean, which is ideal for fit.
That affects the appearance of the various bespoke jackets he
shows in his blog. Personally, I have high square broad shoulders
and am thickly built. My guess is that the house style of only a
portion of the tailors Simon works with would look good on me