A common complaint I hear from blue-collar men is how dressing up is so antithetical to what they have to wear all day long. Nothing is more form over function than what a welder or construction worker wears to work. And since these men wear the same thing day in and day out, it becomes a part of them and is truly comfortable. I’ve seen men with more swagger in a greasy mechanic’s outfit than some kid dressed to the nines in his new suit.
My suggestion is, rather than abandoning the ethos of what you do all day, you should embrace it. If you’re going out for a weekend or are in any social situation, take the time to dress a little better but still acknowledge what kind of man you are and what you do.
If you work in the outdoors, keep the Ranger-issued aviators, wide-brimmed hat and work boots like the man above.
If you work in a shop, keep your greasy sneakers on to contrast with the dark jeans and blazer you’re wearing.
I’ve seen farm hands who use their work gloves when they’re on a motorcycle instead of having bike-specific gloves.
Just make sure you don’t overstep it. I don’t recommend wearing a tool belt or a hard hat on your off time. You don’t want to look like a crappy attempt at “channeling the masculine” on some designer’s runway.