If you’ve been following my ongoing clothing saga — the chore coat search, the Red Wing chronicles, the light duty boot quest — you might have noticed that I have opinions. Strong ones. Possibly unreasonably strong ones for someone who spends a meaningful portion of his life mowing a lawn and cutting firewood. But here we are.
Before I get into the actual makeover update — what Jennifer finally convinced me to replace, and where I landed — I thought it made sense to lay out the underlying logic. These are the principles I apply to basically every clothing purchase, whether I’m buying a chore coat for splitting wood or sneakers for walking 20,000 steps around a European city. Consider this the operating manual.
On Fibers
My strong preference is 100% natural fiber, wherever and whenever possible. Cotton, wool, linen, canvas, duck — yes. Polyester — generally no, with some reluctant exceptions I’ll get to. This wasn’t always a hard line to hold. Back in the 80s and 90s it was genuinely difficult to find natural fiber clothing, and then the pendulum swung back, and then honestly it seems like it might be swinging away again. I’m watching it nervously.
Wool is obviously not without its issues. It pills. But so does polyester, so I don’t count that against it. For outerwear, wool and duck canvas are my personal gold standard — they’re tough, they’re beautiful, and they age in a way that actually improves them. The problem, as anyone who’s tried to pack a proper wool coat into a carry-on knows, is that they’re heavy and they don’t compress. Which is why the travel wardrobe requires some compromises, and why I have a whole separate post about that.
On Colors
I gravitate toward dark, neutral, and natural tones. Blues, greens, browns, bluish greys, charcoal. I avoid black in most clothing, not for any ideological reason but just because it reads flat to me — though I make an exception for outerwear. White I basically never wear, except for undershirts under button-downs, because I am a grown man who goes outdoors and exists in the world, and white just doesn’t survive that.
The general logic is that I go darker on bottoms than on tops. Darker trousers, slightly lighter shirts and sweaters. It just tends to look more intentional, and it hides the reality of my life, which involves dirt, grass stains, and the occasional motor oil situation.
On Pants
I prefer chinos over jeans, mostly because everyone wears jeans and I’ve found I just prefer to not look like everyone else. When I do wear jeans, they need to be a dark wash — I don’t really want to discuss light-wash jeans. I feel about them the way I feel about pleated pants, which is another thing I’d rather not discuss. Flat front, straight fit, not too baggy, not skinny. There’s a narrow Goldilocks zone in there and it’s genuinely harder to find than it should be.
And then there’s the inseam situation, which is its own special frustration. I’m a 31 inseam, which sounds reasonable until you realize that most pants come in 30 and 32, which means I’m perpetually choosing between slightly-too-short and slightly-too-long. I care about this more than most people probably should. I was teased for wearing floods as a kid and apparently that left a mark, because I’d rather deal with the alterations than accept the flood look.
On Shirts
My go-to is a collared prima cotton t-shirt — not a polo exactly, but elevated enough that it’s not just a t-shirt. It’s versatile, comfortable, and works across a wide range of settings. Pair it with a sweater and you can take it almost anywhere. For button-downs, I prefer light blue in 100% cotton non-iron with button-down collars. I also have a soft spot for plaid button-downs, though they tend to run warm, and I find wrinkles less offensive on plaid, which is a nice bonus.
I wear white undershirts under button-downs. That’s really the only white in my wardrobe.
On Footwear
Look, I’ve written at length about this. The Red Wing situation. The light duty boot odyssey. The chore coat hunt. The elastic laces revelation. If you want the full story, I’d point you to those posts. But the short version of my footwear philosophy is: waterproof wherever possible, slip-on wherever possible, moc toe whenever I can get it, and no thin soles. I’m on the shorter side — well, technically I’m average height for an American man, which apparently means shorter than most of the people around me — and thin soles on shoes just don’t look right to me. More practically, shoes exist to protect your feet, and the sole is doing that job, so I want more of it.
I’ve converted essentially every tie shoe I own to elastic laces at this point. The goal is to be able to slip them on and off without touching them, because when you live in a house where you’re going in and out all day, lacing up is not a thing you want to be doing repeatedly. I have accepted that this makes me look like a toddler in my shoe-management process, and I’ve made peace with it.
On Outerwear
Natural fibers again: wool and duck canvas for around the house and town. I have a great vintage black wool coat with a zipper that I’d love to get repaired — the elastic cuffs are shot — and an English wool blazer I don’t get to wear as much as I’d like anymore but that still works beautifully layered over a lightweight puffer in cooler dry weather. I also love waxed canvas, with the understanding that it’s water-resistant rather than truly waterproof — it’ll handle a brief shower but extended wet conditions will find the seams eventually.
For travel, I need something that compresses, layers, and looks like I put some thought into it rather than like I’m heading to a trailhead. Which brings me to the actual makeover.
Continued in: My Makeover Is Just About Complete
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