Oh you could totally pull off a button-up shirt!
Sizing for men’s stuff is way simpler than women’s, it’s either in inches or s/m/l. If you want a polo try medium and large, see which fits better. For pants, look up a conversion or run a string around your waist (masculine waist, not feminine waist, so around your actual hip bones) and measure how long that string is- boom, men’s waist size. (Might be an inch or two off, but that’s it.) Then run a string from your ankle to your waist, measure it- boom, mens pant length. Sizing will be something like 38-40, with 38 being the waist inches and 40 being the length inches.
For button-up shirts, you can try m/l, and try a couple different “fits,” relaxed fit being the squarest and slim fit being a tiny bit tapered. Nicer dress shirts will be in inches, same thing measure and boom. I’d start with a gray or black shirt, since those are kinda more masculine colors and won’t be seethrough like white.
You won’t have a choice for pants color that isn’t masculine, so just match it to the shirt.
I’d go with work-look boots as well, can be men’s or just look like men’s, but this sort of look;
(There are cheaper options, I just couldn’t copy the picture sorry)
The blocky tread will help look rugged, and the leather keeps it classy. The wider toe box makes it distinctly masculine, and also more comfortable. There are women’s-to-men’s shoe size conversions if you google it.
For hair, maybe a half-down kinda man bun? Just a minimal effort bun, and leave a fringe down behind it?
Kinda like that?
