We independently evaluate all recommended products and services. Any products or services put forward appear in no particular order. if you click on links we provide, we may receive compensation.
Let’s Get Real About Some Regrettable Purchases
What do the most iconic boots of all time have in common with the trendiest shoes of all time? They’re both things that I think I regret buying, so let’s dissect.
Hey everyone, it’s me. Today, we’re going to look at clothing I regret buying. Oh, you just want me to get nasty, don’t you? I should say, though, all of these brands are of fantastic quality.
There’s nothing actually wrong with the garments; it’s just me personally. I don’t like them for whatever reason I shall outline in a second, but I would recommend them to you if you like them, and I’ll tell you what I don’t like about them.
Overview of the Clothing I Regret Buying
| Product | Key Features | Pros | Cons | Usage Notes |
|---|---|---|---|---|
| 3sixteen Mechanical Wool Jacket | Japanese wool, lined, slim fit | High-quality fabric, stylish | Slim fit limits layering, long wool fibers resemble pet hair |
Best for light layering in colder weather |
| New Balance 550 Sneakers | Trendy design, comfortable | Great for casual wear, durable | Trend dependency, feels dated when out of style |
Ideal for short-term trendy looks |
| Samuel Zelig Knitwear | Heavy knit, intricate design | Unique style, standout brand | Uncomfortable weight, fit issues |
Consider sizing down; better for lounging |
| Filson Rain Jacket | Water-resistant, durable | Stylish and practical | Wets out quickly, retains heat |
Use in cooler rain conditions |
| Red Wing Moc Toe Boots | Goodyear welt, crepe wedge sole | Legacy brand, durable | Chunky silhouette, high toe box |
Pair with heavy-duty outfits |
That 3sixteen Mechanical Wool Jacket Situation
I was going to start this article off with my most controversial opinion because it has to do with Red Wing and their most famous Heritage boot, the moc toe boot. But I can’t gather everything I need to say it. I keep getting nervous and doubting myself, so I’m gonna put that at the end. We’ll talk about that at the end, but the first thing I’m talking about is the 3sixteen Harry mechanical wool jacket.
It’s fantastic quality, fantastic jacket, but there are a few things that make me just not particular- well, just really, I guess one thing. It’s because a few years ago before I moved to New York, I applied for a job at 3sixteen to be a manager of their New York flagship store, and according to Andrew Chen, I don’t have any managerial experience and have never worked in retail, so if another job opened up they would let me know immediately. Just kidding, 3sixteen! That was a performance. I was just acting.
But either way, this jacket is absolutely fantastic. It is Japanese wool with very, very long hairs that you can pull out, and it looks like dog hair. Initially, I kind of didn’t like that about the jacket because I thought everybody would think I was covered in dog hair.
That’s not an issue, but what always happens with me in 3sixteen, their jacket fits specifically, is it’s always way slimmer than I’d expect, and I’m a very slim, small person. So with something very slim on me, it’s usually very, very tight, and 3sixteen updated their fits over time. Obviously, they open things up. Things got looser, but still, on this mechanic jacket, I probably should have sized up even more because while I really like the jacket, and it’s fantastic, and I’m super glad that it’s lined, it’s a little too tight for me to wear a lot under it, which I like to layer a lot in the winter. So, I guess I could layer over it, but I would wish I could layer under it. But either way, I may keep it because it’s very cool. Say it on three, one, two.
(After reviewing that jacket, me and Michael both think that the old version of Michael looked fantastic in it and that he was totally wrong at the time, so it is definitely a keeper.)
The Whole Thing About Trendy Sneakers
Number two, you probably won’t be surprised, but the reason is not just because they’re New Balance 550s. Those are great shoes; they’re very comfortable, and everything is like that. I can’t recommend them enough, but I bought them when they were very on-trend. I bought them to do a review and figured I would wear them anyway, but I don’t usually try to dress very trendy because when you subscribe to trends, you then have to keep up with trends.
And there’s this like rush of like, “Oh well, all of a sudden these 550s aren’t cool, so if I’m wearing them, people are going to see them and think, well those are out of trend, they’re not cool anymore.” There’s all this head game stuff that you have to think about what’s in and what’s out, and I hate that because if I buy something, I want to wear it for as long as I possibly can. And not that I can’t wear these shoes, but there’s an added layer of “Am I not cool for wearing something that I like, personally?” I’ll probably always obviously get something trendy every once in a while, but it does create a rat race that I don’t- I’m not a big fan of.
The Samuel Zelig Knitwear Dilemma
Number three may surprise you because it’s my favorite knitwear brand of all time. The stuff that they make is absolutely incredible; it’s Samuel Zelig. Their stuff is beyond expensive, but with every single piece I see, I’m like, “Wow, that is an absolute grail piece. How can I live without that $500 sweater?” But there are two things that I regret. Number one, I think I found out about them kind of early, or they were low in stock or low in pieces or something like that – they didn’t have as vast of a collection as they do now, so I bought the piece that I really like then, but now seeing all the stuff that they have, it would probably be my least favorite piece.
Two, the fit on me is just wrong. Maybe I should size down a little bit, but the fit is just that I never feel like I’m wearing a flattering piece of clothing when I’m wearing that hoodie. Also, surprisingly, something that I never really thought I would say is that the weight of the knit is just incredibly heavy to the point where it’s a bit inconveniently heavy. It’s not that comfortable to lay down in, which is what I’m usually doing when I’m wearing a sweatshirt or something like that. I wish it was a lighter knit, and I wish it fit me a little bit better, but I’m going to keep trying because, like I said, that stuff is so cool that I just think about it all the time.
Let’s Talk About My Beef with Linen (Yeah, Really)
This may be the dumbest take of the entire article on clothing I regret buying because it’s not about a piece of clothing, it’s not about a brand, it’s about a fabric. As much as I try to love this effing fabric and heavy weights and light weights and mid weights, really washed, not really washed, in a raw state, I just can’t. But it’s a bast fiber, it dries fast, it’s great in the summer, and it’s called linen.
All right, the wrinkles drive me insane, and my girlfriend Taylor wears linen all the time, and she’s like, “Dude, you gotta embrace the wrinkles,” and I can’t. I hate that it wrinkles. I love how it looks when it’s crisp, I love the shine that it gives, and it does a lot of things that cotton can’t, but the wrinkles make me want to climb up a tree and then chop it down. The feeling of a wrinkly, springy piece of cloth on my body- I could have a hernia right now.
White Sneakers: My Fall from Grace
This one is definitely the stupidest take of the entire article. It’s just because when I first got into fashion, this was all I would wear. I think I just wore it out to death a little bit, and I’ll get back into these things, in general, a little bit later, but white sneakers – I have Stan Smiths, I have the New Balance 550s. I always try to get a different white sneaker when I wear mine out, but just lately, I see white sneakers on my shelf, and I’m like, “Yuck, I’m not wearing you today.” White sneakers are kind of off the fritz, guys, so watch out, fashion alert!
Real Talk About Sizing (Because We All Do This)
This is actually something I recently realized that I do, and I feel like 99.9% of people do this all the time, too, and I noticed it with this vintage pair of Levi’s jeans. These are cut wrong, so they should be a size 27 when they’re labeled as a size 29, but really, I should probably wear a size 30 and, in some brands, a 31. And I should have always, but when I do and what I’m going to try and stop doing is buying the size that I think I should be instead of checking measurements and saying like, “Okay, I’m not a small on this brand, I’m a medium.”
I feel like it’s very easy to be like, “No, I’m a size small,” and if I’m not a size small, it’s because I gained weight when, in reality, different brands have different cuts that flatter you in different ways. So you should always check your measurements and maybe you did gain weight, and even if you did gain weight, that doesn’t mean you should still buy a small and try to fit into it – you should then get a medium or a large or something like that.
Some Thoughts on Fashion “Rules” and Fabric Weights
This last one has to do with the rules of fashion. Obviously, there are no rules for fashion, but I think there are some very, very strong guidelines. As I’m trying to make more clothes for the Iron Snail, I realize it would be weird if this jacket was made of wool and not denim – something about it would feel off, and it would look off. This fabric does not complement this silhouette, and I believe the same thing applies to weights of fabrics. What I mean by that is that different silhouettes and different pieces of clothing have designated weights. A t-shirt is like four to eight ounces on average; a chore coat you wouldn’t want a five-ounce chambray – that would feel like a very big weird shirt.
And there are two things in that similar vein on this Corridor piece. This is an overshirt, so it is supposed to be an overshirt, but we’ll talk about the second thing later. The fabric is a beautiful open weave Dusty Rose. It’s fantastic, but for me, the lightweight and breathingness of that fabric combined with the very heavy Corozo nut buttons makes it feel like the garment is being pulled down right away, as if it’s drooping.
The other thing is that it is constructed – while it is an overshirt, it looks more like a chore coat, and I would like a chore coat to have a beefier feeling fabric. And this kind of rides the line between an oversized shirt and a jacket, which is very popular for people that are not in an area that gets very cold, but for me, where I generally get cold enough where I can wear big heavy jackets. And personally, it doesn’t totally blend with my rules of fashion where something on the outside should be heavier, should be a little beefier and stiffer.
The Big One: My Complicated Relationship with Red Wing Boots
And now we talk about Red Wings. Arguably, Red Wings is the most important Goodyear welted boot brand of all time. I know that’s a very American thing to say but bear with me here. I would also say the Red Wing moc toe silhouette, in general, is what brought Goodyear welted boots back into the forefront of the hipster-dome of fashionista people in the 2010s, maybe the early 2000s – I forget the era specifically. But you can’t be where we are now in Goodyear welted boots with all these new brands and all this new stuff happening without Red Wings, and they were really the rebirth of it all.
But the moc toe boots are kind of like white shoes but are more of a legacy version of that. So, let me outline exactly what I’m trying to talk about. It’s a very silly thing to say in general – I don’t know if I like these boots because of the fashion of them when they were born to be work boots, and they’re used by ironworkers and all that, and I’m like “Well, I think the toe box is a little large, don’t you?” It doesn’t make the most sense, and I’m aware that they’re not really boots for me. I just wear them for fun.
But really, after investigating all of these other boot brands and seeing what I like and seeing what I don’t like, I’ve kind of narrowed down why the most important moc toe is not my favorite, even though it’s a fantastic boot. Starting off with my second biggest gripe, we’ll go into the second one in a second – obviously, you probably could have guessed this – it’s the toe box and the tone wall. Part of the reason moc toes exist is so you can build up a very high toe wall to protect your feet and to keep them comfy in there all day, but it is such a high boot that I would prefer something that just has a little bit more dress factor, and the toe is pointed up a tiny bit, and I prefer boots that are pointed down.
Really, I’m just saying I like dressier boots, which is fine, but that’s one of the reasons I’m not a huge fan of wearing them right now. The other reason, though – having a crepe wedge sole under it makes that block even bigger, and that’s the silhouette that I don’t think I like because I was looking up what Red Wing moc toes look like with just a heavy lug sole, and I like those infinitely better. I think that’s a great look. So, I think it’s a combination of a very blocky toe wall and a very blocky outsole, which doesn’t really jive for me perfectly.
Plot Twist: Maybe I Was Wrong About Everything
I would just like to announce that I completely take it back. I love these boots, and I think they’re the most beautiful boots that I’ve ever seen in my entire life. I don’t know what I was thinking three seconds ago. I have no idea what my opinion is on these boots, you know, whatever.
Watch This Review
Wrapping This Up
Anyways, that’s it on clothing I regret buying, mostly. I’ll see you all very, very soon. Goodbye!
This article was adapted from Michael Kristy’s video on The Iron Snail, with edits from FashionBeans, and was reviewed by Michael to ensure the integrity of his original content. Watch the full video here.
The Iron Snail is a men’s fashion vlog (and now article series!) starring a young man named Michael and featuring a snail no bigger than a quarter. The two are set on taking over the world of fashion by creating a clothing line to end all clothing lines. Until then, we’re here to tell you EVERYTHING you need to know about the best clothing out there, from the highest quality raw denim jeans to the warmest jackets to the sturdiest boots…the Iron Snail has got you covered.
