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