I'm mostly repeating what others are saying but, as a lesbian, who has been somewhat butch at times, I feel like I can contribute to this.
As a kid, I was a tomboy. I typically wore jeans or shorts because I was climbing trees or playing sports. The only exception to that was while cheerleading, which I did for 8 years. We wore bloomers under our skirts. Aside from football season, while in uniform, I was not comfortable wearing skirts or dresses. Part of that may have been from being corrected if I did anything that could potentially show my underwear; cartwheels, hanging upside down from things, sitting with legs uncrossed, etc.
As I got older, I wore what was comfortable. Jeans, t-shirts, hoodies, sneakers. I wasn't particularly interested in doing my hair or wearing makeup, it wasn't something my mom did, and it was never incorporated into my getting ready routine. I experimented some as a teenager (mohawk, dyeing my hair, goth makeup for a brief period). I wasn't interested in the makeup everyday thing.
When I turned 18, I decided to cut my hair short because it was more convenient. I looked boyish or androgynous but it wasn't a fashion statement, I was just comfortable. Throughout my early adulthood, I grew my hair out some, had a faux hawk, cut it short, had it completely shaved (buzzed down to a 1 or 2 guard) for a few years, and eventually let it grow out.
I never considered myself to be butch or tried to look like a man or look like anything for anyone. I've always done whatever was convenient or comfortable at the time.
In my twenties, I started bartending at a gay nightclub. I realized that I could maximize my tips by reading more ambiguously. So, I let my hair grow to around chin length, put on a bit of makeup, and went to work. In my experience there, gay guys appreciate it when someone puts effort into their appearance, straight guys couldn't tell if I was a lesbian or not, I was androgynous enough that femme lesbians were into me, straight girls couldn't read me and didn't think I was competition, femme enough that butch girls were into me. So, my bartending warpaint worked out perfectly. I briefly bartended at a strip club, but the outfit required made me feel ookey. Cleavage and booty shorts are for displaying your shit, not your ability to pour a bomb ass drink. Because of this, I did not work there for long.
Since then, I learned the value of "the mask." I have no problem with throwing on some simple makeup, sometimes it makes it easier to face the world when you feel like you're in disguise. I was in a relationship at one point where, for reasons based on who she was, I typically regularly wore makeup and put a little bit more effort into my appearance (nicer t-shirts and jeans with clean sneakers) while in public with my girlfriend.
My hair is now almost down to my butt. I still just wear jeans, t-shirts, and hoodies. Apparently, while I thought I had some degree of straight passing privilege, people can clock me as a lesbian from 20 feet away. I've been told I walk with purpose and make direct eye contact. Didn't realize that was a lesbian thing but I don't question the science of gaydar.
I don't think I was ever as butch as you're referring to, but back to your question. I wasn't dressing like or trying to look like a man. I was dressing comfortably. Anything related to men or looking like a man or being attractive to a man never crossed my mind. I hoped to be attractive to women, depending on whether or not I was their type, but I didn't change to conform to any of those types. I'm just me. Not that it matters, but I've had many relationships and dated plenty so, whatever I've been doing while just being me, it must work. (: