I got my hair cut Friday  night. I asked for a pixie cut and showed her a picture, and she dutifully cut and styled it that way. Saturday, I washed all the gunk out, and styled it in a nice masculine side part, and trimmed the "sideburns" to be closer to level instead of pointy Then I shaved my facial hair.

Today, I donned sports bra, t-shirt, jeans, and the most male looking shoes I own and went shopping. I put stuff in my pockets instead of carrying a purse. I'm sure I didn't "pass," but some people looked confused. I got jeans, khaki pants, and black pants, a couple of short sleeved Henley t-shirts, a pair of sneakers, and a double sided belt, ALL MEN'S! When I got home, I put everything on again in front of the mirror and was positively giddy to have clothes that fit and were comfortable! I still need to find some collared shirts I can wear to the office, but at least now I have stuff I can wear out that doesn't scream "GIRL!"

Question: The only passable men's shoes I have that are appropriate for the office are brown. Can one wear brown shoes and belt with black pants? I looked at men's black shoes but they all seemed "clunky" so I didn't get any. The men's size 7 sneakers I got fit my feet perfectly - love!

Quote from: JayDawg on March 23, 2014, 07:54:01 PM
I got my hair cut Friday  night. I asked for a pixie cut and showed her a picture, and she dutifully cut and styled it that way. Saturday, I washed all the gunk out, and styled it in a nice masculine side part, and trimmed the "sideburns" to be closer to level instead of pointy Then I shaved my facial hair.

Today, I donned sports bra, t-shirt, jeans, and the most male looking shoes I own and went shopping. I put stuff in my pockets instead of carrying a purse. I'm sure I didn't "pass," but some people looked confused. I got jeans, khaki pants, and black pants, a couple of short sleeved Henley t-shirts, a pair of sneakers, and a double sided belt, ALL MEN'S! When I got home, I put everything on again in front of the mirror and was positively giddy to have clothes that fit and were comfortable! I still need to find some collared shirts I can wear to the office, but at least now I have stuff I can wear out that doesn't scream "GIRL!"

Question: The only passable men's shoes I have that are appropriate for the office are brown. Can one wear brown shoes and belt with black pants? I looked at men's black shoes but they all seemed "clunky" so I didn't get any. The men's size 7 sneakers I got fit my feet perfectly - love!

No you definitely can't wear black pants and brown shoes.  Glad you are feeling good with your purchases, though. 

I just went shopping for men's clothes last week. It's great isn't it. I've been having so much fun wearing them.

I can't answer your question about the shoes. Apparently I'm clueless in both genders.

Well you can wear a brown belt with any colour pants as long as it matches your shoes.

Congrats! It's wonderful to start seeing the real you emerging. 

As for shoes... if you can't find appropriate shoes in the men's section, have you considered trying the boys' section? I've found some great formal shoes and loafers there that look perfect for the office, and they don't look as 'clunky' as some of the ones in the men's section.

I've always believed that you can't wear brown shoes with black trousers but more and more people seem to be doing it. They're going for the highly polished pointed kind of shoe and although I can't quite bring myself to do it some of them look ok

I usually wear a mens' 7.5 but I had a lot of luck finding really simple basic black formal shoes at Target in the boys section. For some reason I wear a 7.5-8 in most tennis shoes but I wear a boys' 5.5-6 in formal shoes. They look good enough, plus they were only about $20 since they were kids instead of mens. They're not high quality or anything, but if you need black shoes, it's a good inexpensive option.

I don't know if you have a Target where you live, but if you do, I'd definitely recommend looking there.

Brown shoes, brown belt, and a neutral colored collared shirt will work with black pants.

- fashion nazi

Thanks, everyone!

I'm not terribly fashion conscious regardless of my gender, so I won't even try to pull off black pants and brown shoes

I figured out why men's shoes look clunky; it's because the sole and stitching is visible around the body of the shoe. Women's shoes come together even with the sole, so you don't see soles and stitching when you look down. This just bugs me.