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

[beanmachine314]

I'm surprised that you generally found high-rise trousers to look less flattering for your gut instead of better - that seems against conventional StyleForum wisdom. Did you try any that also had pleats?

Agreed, high rise and pleats make the bit of extra I have around the middle seemingly disappear. High rise with no pleats always looked a bit odd though.

 

[jdgershbein]

I see a correlation between paying school dues and the views expressed in another post I am following here in SF on mental health and clothing.

My style journey began in my early 20s and has taken me through many twists and turns. I’m still trying to find my pure, unadulterated taste, although I am closer than ever. For many years, I was a CM disciple and populated my closet with clothing in hues that conformed to the accepted business palette. I was an old-school, professional speaker who believed in “situational dressing” and respecting my audience with my apparel choices. Through the years, I have spent—A LOT—on clothes, an expensive process of discovery that has been both enjoyable and agonizing. If something didn’t work, I wrote it off as a cost of doing business.

I show up differently these days. Whereas I still believe in dressing for the situation, the pandemic bestowed me with a certain autonomy and relaxed my norms. As the necessity to wear a suit and tie diminished, my right brain took over, and my school dues mounted. I have again reshaped my perceptual framework to see what would work and what would not.

Yes, I have succumbed to the lure of athleisure and comfy, stretchy fabrics for working more from home. My penchant for fine knitwear and outerwear has displaced more sartorial choices, damping the urgency to acquire another charcoal gray, tan, or navy blue suit. I favor the sports jacket and the upscaled chino as my business armor. As for footwear, I’ve traded the whole cut for double monk straps and, on my more rebellious days, the Chelsea boot or dress sneaker.

Since gravitating away from a CM-heavy wardrobe, I approach my exact taste asymptotically, hovering over it and hoping to land. On this leg of the journey, I am trying to minimize, if not neutralize, purchase remorse. I’ve paid a fortune in school dues getting to this point, and I am still trying to figure out who this person is underneath all the impulse buys.

Style is an exercise in trial and error, and I love a good experiment.

 

[Son Of Saphir]

So, I'm not nearly as experienced or deep into my journey as most of you are, but I've already noticed some marked style preferences that I've developed and realized the many "school fees" I've payed. These are, I would suppose, part of a curve in learning that might seem usual for many, but that I only understood after experiencing it for a while.

For example footwear: I used to love, aesthetically, very chiseled, narrow and sleek lasts in oxfords and even loafers. I also privileged smooth leathers to grain or suede. This was before I understood the big difference in elegance vs casualness that these styles of shoe make, and also the fact that, since changing jobs, I don't wear proper suits that often, even if I try to wear jackets and trousers as often as I can. But after gathering a collection of this style of shoe, now I've realized that buying more rounded lasts and textured leathers is much more versatile, not only for denim, but also for chinos or odd trousers with jackets. So now aesthetically I really appreciate rounder, not so elongated lasts and my chiseled sleek lasts get little wear. The other significant discovery I made concerns the shape of my feet, and the kinds of last that fit it. I have stopped choosing lasts that only look good, and now I first of all try the lasts for fit. For instance, I have discovered I have narrow heels, so now I know that only lasts that are very well shaped in the heel, that preferably have leather board or full leather counters are significantly better for my physical AND mental health.

The other is, as can be expected, tailoring fit: when I was working as a lawyer, and I had to wear suits everyday, I used to buy those horrible poly suits two sizes too big. I then changed jobs, and stopped wearing suits for a while. Then I got back into tailored clothing. But at the beginning, I felt I needed to correct years of aesthetic horror with super slim silhouettes. And then I realized that this look is not only a little weird, but super uncomfortable. Also, I discovered that it is dangerous to rely on tailors who themselves do not wear a lot of tailored clothing, since all they care about is getting rid of extra fabric in the static pose you stand on when they're pinning you, especially on the back. BUT, the beautiful thing about high quality fabrics, light or heavy, is how it flows. For that, I discovered, some drape is needed. Movement is what gives tailoring its grace, as opposed to the stiffness of more casual clothes like denim or thick cotton, I've come to understand. And for that, one needs some ease or a bit of extra fabric. But, I then discovered, this is only on key places, and not everywhere (i.e. not on the shoulders, or the waist). So now I prefer a little drape on the chest and skirt, but with well waisted and soft, perfect fitting shoulders. I do have some regularly squared shoulders, and am tall and lean, so I understand that this might not work for everyone. But I've come to aesthetically prefer, and find a lot more flattering and less pretentious, less constricting clothes which give me comfort in movement, and that flow beautifully with the wind. Since what's the purpose of obsessing about full canvas and hand padded lapels if they fit skin tight and don't move, or if they're burdened by a lot of structure and foam?

I know that not everybody feels the same, but the point I'm trying to make is that I appreciate this thread as a way to reflect on an ongoing journey, and also to share the satisfaction of getting rid of all those costly mistakes, whether on eBay or good will, or even, since I'm in the city (NY), by making many migrants sent over by Abbott happy with well cared for clothes that can make them look presentable in their immigration processes and requests.

All my experience.
Avoiding the stunning elongated shoes with slim fiddleback waists,
avoiding the higher pitched heel.
Find shoes that work for the body and clothing instead.

Most important,
understanding fit and having clothes made that allow for movement and comfort while being clean fitting.
Not all perfect fits here work for everyone.
Understanding the tradeoffs with clothes.
Clothes cut for the body,
knowing what works for you.
No forum can teach you that.
No forum can teach style.
Style is acquired over time by realising what works for you.

French cuff shirts,
sound good but urk.
Many recommendations on forums don't work for me.
Learning what works for you is when clothes become really enjoyable.
Learning that brown shoes can complete an outfit in a way no other colour can is a great moment of realization.
Realizing how a shirt should fit is a great realization.
You finally become at peace with your wardrobe because you have finally worked it out.
You know the fits and the colours and the types of shoes needed.

 

[Son Of Saphir]

how many of those perfect fits you see lack room to move in the clothes.
my tailor tells me many compromise comfort for fit.

 

[beanmachine314]

I see a correlation between paying school dues and the views expressed in another post I am following here in SF on mental health and clothing.

My style journey began in my early 20s and has taken me through many twists and turns. I’m still trying to find my pure, unadulterated taste, although I am closer than ever. For many years, I was a CM disciple and populated my closet with clothing in hues that conformed to the accepted business palette. I was an old-school, professional speaker who believed in “situational dressing” and respecting my audience with my apparel choices. Through the years, I have spent—A LOT—on clothes, an expensive process of discovery that has been both enjoyable and agonizing. If something didn’t work, I wrote it off as a cost of doing business.

I show up differently these days. Whereas I still believe in dressing for the situation, the pandemic bestowed me with a certain autonomy and relaxed my norms. As the necessity to wear a suit and tie diminished, my right brain took over, and my school dues mounted. I have again reshaped my perceptual framework to see what would work and what would not.

Yes, I have succumbed to the lure of athleisure and comfy, stretchy fabrics for working more from home. My penchant for fine knitwear and outerwear has displaced more sartorial choices, damping the urgency to acquire another charcoal gray, tan, or navy blue suit. I favor the sports jacket and the upscaled chino as my business armor. As for footwear, I’ve traded the whole cut for double monk straps and, on my more rebellious days, the Chelsea boot or dress sneaker.

Since gravitating away from a CM-heavy wardrobe, I approach my exact taste asymptotically, hovering over it and hoping to land. On this leg of the journey, I am trying to minimize, if not neutralize, purchase remorse. I’ve paid a fortune in school dues getting to this point, and I am still trying to figure out who this person is underneath all the impulse buys.

Style is an exercise in trial and error, and I love a good experiment.

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.

 

[Son Of Saphir]

Heavy school fees:

1). buying 100 pairs of socks from non traditional sock makers who are new to the industry like Viccel.
Most wool/silk combos have developed holes in all types of places after some wear.
Waste of money and too many dogs to count.
Best to pay proper money and buy from sock makers who make more consistent quality.

2). Buying super elegant bespoke shoes from Cleverley.
They fit good and look great,
but they make my feet look tiny.
Some men look good with elegant shoes,
but some men look terrible.
Me look terrible.
Me too embarrassed to wear Cleverley and G&G now.

3). Buying Hermes made in Scotland cashmere scarves that are too short.

 

[sam67]

I did a lot of thrifting so had time to figure out shirt and pants fit, then lost 20 lbs. and started over. My biggest error was Ace Mark shoes. I should have saved the money and bought a vintage USA make and resoled it. I did keep them though and dyed them green.

 

[Proleet]

-Shoes on sale that end up being too tight
-too many shoes for niche outfits
-velvet blazer I never wore
-some sweaters that were too tight or just not really my style

 

[jdgershbein]

Purchases that seemed a good idea at the time, anticipated as valuable acquisitions to the wardrobe, but are now deemed remorseful acts, call for more acute 20/20 hindsight.

You know, it takes maturity to realize you paid school dues.

 

[asubtleeffort]

• Slim-straight jeans and five-pockets that are snug in the seat and thigh but too large in the waist. Have to be cinched tight with a belt and I'm constantly pulling them up off my hips.
• Been through a couple of slim suits and sport coats with skinny lapels like everyone else
• Several oxford shirts with fused collar and cuffs and sleeves too short to wear with a sport coat - these were cheap so it's a good thing I figured this out early.
• Several dress shirts in the wrong neck size (1/2 size too small). The chest and shoulder fit perfectly but I feel like I'm being slowly choked.
• Several white oxford shirts that I collectively wear twice per year.
• Buying three billowy BB oxford shirts without checking the fit because there was a deal.
• Getting fitted into oxford shoes a half size too small by a salesman.
• Grey trousers in smooth super 120s wool. Now that I have a pair of flannel trousers and a pair of cotton-linen trousers, these look like the orphaned bottom half of a suit.
• Expensive alligator belt and engine-turned buckle - I am moving towards side tabs on my trousers, so these probably won't see much use unless I'm wearing a suit.
• Letting a great BB tweed sport coat go because it didn't fit the slim-skinny mold of the 00s and seemed "too large" (I previously had it altered to take in the waist and was talked into adding shoulder padding...)
• A waxed jacket that's too tight in the sleeve to comfortably layer over a sweater (maybe it's good to have for the "transitional" season?)
• Iron Rangers collecting dust in my closet - maybe I'll use them for yard work?

 

[gimpwiz]

I've been thinking about this thread, as I've discovered a little too much attraction to ebay.

So far, I've got three categories of purchases:

1) Really excellent stuff, at a fine price. (Way less than original sale price, but not diamonds-in-turd-bowls prices.)

2) Pretty decent stuff, at a very good - to - excellent price.

3) Misses, at really really low prices. These were priced low for a reason...

Maybe some day I'll get ambitious and take some photos, of the stuff that worked great, the stuff that worked fine, and especially the real misses that'll have to be passed onto someone else. "Ugh," you'll say, "what was he thinking? He looks absurd." Yep. True.

Anyone here have some good stories of absolute whiffs? Stuff you were excited for, bought for very little, and then realized it's just not going to work out at all? Especially stuff that cannot be returned, because it was on close-out sale / thrifted / etc. Or stuff that's too inexpensive to bother, even if the seller didn't measure something correctly.

 

[jdgershbein]

Typically, when exploring new brands on eBay, I'll research before pulling the trigger. I have learned that, even with due diligence, bad decisions lurk around every corner of the site.

My biggest swing-and-miss was on a denim cotton overshirt from Engineered Garments. It looked so cool in the photos -- the seller published shots from many angles on the listing -- and the measurements were spot-on.

It was pricey, and the seller did not offer returns, but I bit.

It took a few weeks for the garment to arrive from the UK. My expectations were high. I tried it on and could not have been more disappointed. It was about as unflattering a drape as could exist. And it telegraphed cheap.

I studied myself in the mirror and tried (really, I did) to make it work. I thought, 'Should I take it to my tailor?' and spend another $40-50? The revelation was that the piece was just too off-style for me.

I paid the school dues and donated the item.

Never again. Until the next time.

 

[beanmachine314]

I've been thinking about this thread, as I've discovered a little too much attraction to ebay.

So far, I've got three categories of purchases:

1) Really excellent stuff, at a fine price. (Way less than original sale price, but not diamonds-in-turd-bowls prices.)

2) Pretty decent stuff, at a very good - to - excellent price.

3) Misses, at really really low prices. These were priced low for a reason...

Maybe some day I'll get ambitious and take some photos, of the stuff that worked great, the stuff that worked fine, and especially the real misses that'll have to be passed onto someone else. "Ugh," you'll say, "what was he thinking? He looks absurd." Yep. True.

Anyone here have some good stories of absolute whiffs? Stuff you were excited for, bought for very little, and then realized it's just not going to work out at all? Especially stuff that cannot be returned, because it was on close-out sale / thrifted / etc. Or stuff that's too inexpensive to bother, even if the seller didn't measure something correctly.

This thread has also been in my head lately as I get rid of even more past purchases as we're significantly downsizing our housing situation soon. I tossed (donated) 4 pairs of Brooks Brothers trousers that I got on sale several years ago. Originally around $200 I paid $30 something for each. I understand why they were on clearance though, because they were such odd colors that I couldn't really match with much of anything. 2 grey pair and 2 blue pair (oh, how I hate blue trousers now), that I could never really wear. The grey pairs were dark enough that I looked like a waiter if I didn't wear a jacket but looked way to dressed up if I did wear a jacket. The blue pairs I just never had any other clothing that coordinated well (all my jackets are blue or green). Those pants, along with:

6 pair of brown trousers in different fabrics (including a beloved pair of almost new Bill's Khaki's that I thrifted for $5, but were always just a little too tight)

3 pair of grey wool trousers

4 pair of green trousers

7 different shirts of varying patterns (I've realized I'm not a pattern person)

3 pair of shoes

and 2 jackets were all boxed up and given to Goodwill after Christmas, and when I'm back home I have plans to do another cleanout. The last trip probably accounted for around $1,000 of 'school fees', mainly because I used to thrift a lot of my clothing. At least I've learned what I don't like now.

 

[A12321]

I can relate to this topic. This has been a very expensive journey over the last several months and the costs are still piling up. I thought I knew everything until I found out I knew nothing. The best part of it honestly is getting rid of the stuff that you realize was so wrong once you're 'enlightened'.

New mantra is quality over quantity, and at the proper expense. Costs continue to accrue but am at least enjoying it.

 

[Bayou Tiger]

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.

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.