How Not to Dress Well: Learning From my Past Style Mistakes

As much as I love learning, discussing, writing, and obsessing about the quality and craftsmanship of the clothing that I wear, the whole point is to wear it, right? While many of us Amekaji weirdos do care a lot about the quality of our clothing and how it ages, we also care about how our clothes make us look as well… or at least I hope we do. I know that I certainly care just as much about wearing outfits that look good as I do about wearing individual garments of high quality.

I feel like it is time for me to post more articles and photos about style on this website in addition to my editorials and product review and I figured the best place to start is with pointing out my own mistakes that I have made in the past and learned from. In truth, I did write a few articles about style in the past and I used to do my Icons of Style series, but I think I have a much better understanding of style now and also want to focus more on my own style. Additionally, it has been a while since I wrote anything like that so I do feel that this will be a pretty new thing on this site. Hopefully, I can help prevent others from making the same mistakes that I have made in future articles, I can provide some level of insight into what makes outfits look good..

Here are the major mistakes that I used to make:

1.Wearing my favorite pieces instead of the best outfit
2.Buying clothes that do not fit me properly
3.Wearing way too many accessories

I am sure there are many other mistakes that I have made, but these are the three that I will be focusing on today.

1. Wearing my favorite pieces instead of the best outfit

This is actually a mistake that I do not think that I have made too many times, but I definitely have made it more than once and I always feel bad looking back at the photos when I do actually do this. Honestly, this is a mistake that people across all subcultures of style make so this is definitely something that is worth talking about. Worst of all for me, this is a mistake that I made just over a year ago in a very bad way so this will be the example that I will focus on for this article.

In December of 2019, my favorite bootmaker, Show Goto of White Kloud Boots was going to be coming to California to visit as well as do fittings and taking orders for a lucky few people. Obviously, I was going to be wearing my White Kloud boots every time I saw him that week, but I also like wearing leather jackets and there was a big problem with that. This issue was that the two leather jackets that I owned at the time that would look good with my White Kloud boots were on the other side of the country having their sleeves shortened so they would look better on me. This meant that the only two leather jackets that I still had were my black and brown Freewheelers Mulholland jackets.

Obviously, wearing black with brown is illegal so I couldn’t do that. This meant that I decided to wear the brown one. The only issue with this is that this particular leather jacket is a pretty dark brown color and my White Klouds are a much lighter, golden-orange color. The two colors really do not look good together at all. In fact, they go about as well together as black and brown do. On top of this, I wanted to show support to Railcar Fine Goods who were hosting the fitting session by wearing my Railcar Fine Goods trousers which were olive green. These trousers look great with either the boots or the jacket, but with the two leather colors combined, the green color just added another distracting tone. As a result, this outfit looked absolutely atrocious. I should have just swallowed my pride and not worn the leather jacket, opting for a denim jacket instead.

This outfit was a perfect example of wanting to wear favorite items instead of wearing an outfit that looks good. Can you sometimes incorporate a couple of specific items together into an outfit successfully? Yes, but not always. These boots and this jacket just did not look good together at all and the trousers just made it even worse. I only wore the leather jacket when I was at the fitting event. I knew that it was not actually a good look and on the other days that I saw Goto-San, I wore a denim jacket instead which looked a bit better. That’s the issue- even when I was wearing the outfit, I knew that it was not good. I wore it because I felt (and still feel like) I am known for my leather jackets and I wanted to wear a leather jacket when seeing a group of fellow boot enthusiasts. This is not a huge deal of course, but I do regret wearing the dark brown Mulholland that day.

2. Buying clothing that does not fit me properly

The previous mistake is one that I definitely made, but not all that often. For the most part, I did know to avoid that issue from fairly early on. However, this next mistake is one that I made quite often. For quite a few years, I simply did not buy clothing that fit me properly. One of the issues was that I thought slim jeans and trousers looked good on me. Obviously, I now believe that they don’t actually look good on anyone except for extremely skinny rockstars who can get away with wearing whatever weird getup they want on stage. Even without that being my belief however, my jeans did not fit me well at all in the past.

Part of the issue was that I only looked at the waist measurements of jeans and did not pay attention to equally if not more important measurements such as the rise and thigh. For some reason, I thought that wearing the slimmest jeans possible would make me look slimmer… which I now know is about as correct as thinking that cheeseburgers are healthy. To top this off, I would buy shirts that were also too small for me and wore them untucked. As a result, I looked sloppy and I simply revealed my weight more than I needed to. Funnily enough, now that I have lost weight, all those too small shirts fit me really well now, but the point is that at the time, they did not fit me.

In fairness to me, one of the major issues that I was facing was the fact that I was short and overweight at the same time. Buying items that actually fit my chest, waist, and hips meant buying something that was massively too long in both the body and the sleeves and usually ended up looking sloppy on me. In some ways, I couldn’t win. However, I was able to find shirts that did actually fit me fairly well and I should have just bought more of those instead of trying to buy shirts that I thought looked cool that did not actually fit me.

My jeans and trousers situation was worse, however. I have quite a lot of pictures of me wearing trousers that simply did not fit me well and it is very obvious from the pictures that this is the case. This isn’t even just a weight thing. If I was skinnier at the time, I still probably would have undersized everything and it still would have been uncomfortable and everything would have looked too small on me. Having been a short overweight guy and now a short guy in pretty good shape with a chest that is still very large (42” at 5’7”) I can say that while it is easier for me to get items that fit me well, it is still not a cake walk. I am sure that people of most body types experience this issue.

At the end of the day, everyone has to look at their measurements and the measurements of the item they are buying or try on the item and see if it really does fit well and fit comfortably. In my opinion, the coolest and most mature thing you can do in terms of style is accept that a certain item just will not fit you and walk away from it, no matter how cool looking it is. I have finally been able to do this with leather jackets recently, realizing that no matter how much I want a Freewheelers La Brea and Real McCoys J24, they probably will not fit me and until I can try them both on at my current weight, I cannot buy them. A few years ago, I would have just bought them both anyway and had them look terrible on me.

3. Wearing too many accessories

This is the most embarrassing of all the style mistakes I have made. One of the things that Youtube style channels all preach is that accessories are the way that you show your personality and really make the outfit yours. What a load of garbage. Sure, you can have certain accessories that become signature pieces for you, but you should not rely on them to actually make you look stylish. Plus, you show your personality and personal style just as much if not more with the actual clothing that you wear.

Having a certain accessory that you wear constantly won’t actually be called your “signature item” if you aren’t otherwise well dressed. Accessories don’t raise the level of a mediocre outfit up to great or even good. In fact, they just make you look even more try hard and lame. Let’s take a look at Fred Astaire as an example. He was well known for using silk neckties as belts. This worked for him because he was already a well dressed individual who was known for his sense of style. As a result, the use of neckties as belts was seen as a unique signature flair for him, but if he was poorly dressed and did this, people would just think he had absolutely no idea what he was doing.

I am the perfect case in point for being the opposite of Fred Astaire. After I was wearing jeans and shirts that were too small for me, I moved into wearing far too many accessories. I looked like a plastic Christmas tree. In a single outfit, I would wear 2 or 3 rings, about 5-7 bracelets, sometimes a watch, a wallet rope or chain, about 15 pieces of junk on my keychain, and then a deathly hallows pendant on a separate key chain. Yeah… I was a complete idiot. Actually, I am quite disappointed that so few people called me out for how stupid this looked. I’m sure people did behind my back and rightly so, but I am annoyed that nobody had the good sense to say it to my face. I only remember one person suggesting that I wore a lot of accessories on The Fedora Lounge, but even they didn’t actually tell me to stop. What made things worse was that I was always wearing sunglasses and hats which apparently are considered “accessories” by people today.

Depending on your definition of what an accessory is, I suppose you could call both of these accessories. I personally see hats as just another item of clothing and sunglasses to me are an absolute necessity, but I will admit that with the other stuff I had on me, these items only further enhanced the size of the junk pile. The sunglasses are a big sticking point for me. I don’t have anything medically diagnosed, but I simply do not step outside without a pair of sunglasses unless the sun is fully set. I despise bright light and maybe I do have some sort of sensitivity to it. Even in overcast weather, I still feel like outside is too bright for my taste.

This is also why I don’t think that wearing a hat and sunglasses is overkill. On seriously sunny days, having both a pair of sunglasses and a hat is extremely helpful. For me, a hat is never enough to shield my eyes from the deadly lazer known as the sun. Even with sunglasses, the brightness of that evil life giving death ball is too much and having a hat is helpful on top of a pair of sunglasses. Of course, there are many times that I am wearing a hat just for style and for the past year, I have worn hats more than ever because I haven’t been able to get proper hair cuts (thanks COVID), but I do think there are actual practical reasons to wear both and either way, I don’t think they look weird together at all.

With that minor detour aside, I still have to condemn my younger self for trying to look like Steven Tyler sans scarves. Since these dark days, I have shed the wallet chains, the deathly hallows pendant (I still love Harry Potter though), bracelets, watch, and 90% of what was on my keychain. Now, I just have the sunglasses during the day, hats sometimes, two rings, and a rather light set of keys and as I said before, sunglasses are an essential for me so I don’t personally count them. Today, my outfits simply speak for themselves. Not everyone may like them, but I am putting all of my confidence in the actual outfit and not the accessories because the actual clothes you wear are what people notice more than your watch, rings, or other accessories. You can add some of these if you want, but just remember that your outfit is essentially the same level of quality with or without them.

To be clear, me writing this article does not mean that I think that I suddenly have everything together and that I am the epitome of style now. There are things that I am doing now that I am sure that I will look back on as mistakes and there are even some things that I know that I need to correct even right now. For example, I am terrible at getting the cuffs right on all of my trousers. My friend John has suggested that I really need to stop cuffing my chinos and just get them hemmed to the proper length and he is right. My chinos look sloppy with some of the cuffs that I do and have done in the recent past. COVID has kept me from getting these hems done, but I will be able to get this done soon. Some people may still say that my wearing of sunglasses with hats is tacky, but I have already addressed why I do this and why I would disagree with this.

Either way, I do at least know some of the mistakes that I made and I hope that you can learn from them as I now have. Part of the reason that I am writing this article is because I wanted people to know that I do not see myself as a perfect arbiter of style. I will be writing some more articles on style and sharing my outfits more often on this website so I wanted to serve myself a slice of humble pie before I get on my high horse and start preaching about how to dress well. The reviews and editorials will continue as well of course, but I wanted to add more style elements to this almost vintage website. I hope you enjoy that.