Anonymous
Post 01/07/2026 22:27     Subject: Middle-aged tomboys
50 year old tomboy and can relate to many of you. I definitely feel like a woman and am happy to be one. I also have a math degree and am pretty handy around the house. I’m
Married to a man and have two kids and find that I’m super traditional as far as how I behave as a mother. I just don’t like clothes that constrict me and makeup makes me feel like a cheat, like I’m pretending to be better looking than I am. I don’t think I could bring myself to wear makeup up as other posters have said, even for a management position.
Anonymous
Post 01/07/2026 21:13     Subject: Middle-aged tomboys
I'm a 53-year-old tomboy. I like wearing band shirts, jeans and sneakers. I like doing DIY stuff and spending time outside. I don't wear much makeup or spend much time on hair and nails. I have a lot of guy friends but get along with women pretty well, but don't have much in common with the girly-girls.
Anonymous
Post 01/07/2026 20:59     Subject: Middle-aged tomboys
Anonymous wrote:I have always been a tomboy and still am. My husband doesn't care, obviously, he married me. I really don't understand the gender neutral thing, because I never questioned that I was a girl. Of course I was a girl!, just a girl who liked to wear pants, have short, unfussy hair, and who didn't want to be hemmed in by expectations of femininity for girls. I didn't see why I couldn't like both of what others classified as "girl" things and "boy" things and have both girls and boys for friends. I have always found it easy to talk to both women and men. I don't think it has ever harmed me socially.


Same! I was always a tomboy, but never questioned that I was female either. Happily married to a man. I have never worn skirts, dresses or heels, played a lot with boys growing up, but also always had close female friends. Only had a courthouse wedding, so no dress either. I think my family and friends would have found it more confusing if I had worn a dress for my wedding!
Anonymous
Post 01/07/2026 20:23     Subject: Middle-aged tomboys
Anonymous wrote:I was never a tomboy growing up but I think some people view me that way now. I think as I get older, my face has a less feminine look to it. I have always dressed pretty much the same, in a lot of classics that can run unisex -- oxford shirts, straight leg jeans, crew neck tees and sweaters. I dont' look like a man but I don't go out of my way for my clothes to look feminine. Same with hair and makeup. I have longish hair and wear makeup most days but I guess it's understated.

A friend of mine says I don't look like a tomboy, I just look German. This is a good description of it.


Ha! I posted just a moment ago and maybe I'm not a tomboy, I'm just German. Most of my ancestors were Germans.
Anonymous
Post 01/07/2026 20:21     Subject: Middle-aged tomboys
I have always been a tomboy and still am. My husband doesn't care, obviously, he married me. I really don't understand the gender neutral thing, because I never questioned that I was a girl. Of course I was a girl!, just a girl who liked to wear pants, have short, unfussy hair, and who didn't want to be hemmed in by expectations of femininity for girls. I didn't see why I couldn't like both of what others classified as "girl" things and "boy" things and have both girls and boys for friends. I have always found it easy to talk to both women and men. I don't think it has ever harmed me socially.
Anonymous
Post 01/07/2026 19:47     Subject: Middle-aged tomboys
Anonymous wrote:I was never a tomboy growing up but I think some people view me that way now. I think as I get older, my face has a less feminine look to it. I have always dressed pretty much the same, in a lot of classics that can run unisex -- oxford shirts, straight leg jeans, crew neck tees and sweaters. I dont' look like a man but I don't go out of my way for my clothes to look feminine. Same with hair and makeup. I have longish hair and wear makeup most days but I guess it's understated.

A friend of mine says I don't look like a tomboy, I just look German. This is a good description of it.


Ha, German is a good one. When I was a kid in a homogenous Midwestern suburb, moms were always asking if I had moved with my parents from Boston. I did have a bob and wore a lot of lambswool sweaters and oxford shirts. In my mind it read “preppy girl”, but in my suburb it didn’t work with the stirrup pants-and-big-bangs crowd and instead translated as “tomboy”.
Anonymous
Post 01/07/2026 18:31     Subject: Re:Middle-aged tomboys
Anonymous wrote:
Anonymous wrote:I'm a tomboy. I have 7 brothers, no sisters. I still prefer men's clothes. I do buy men's sweaters/sweats/etc.

When I wear dresses, etc I feel like I'm cosplaying.

I've found ways to "dress androgenous" in a way that is "stylish" ... more so than sweats.

I did wear a dress when I married but the idea of a wedding dress was just too much cosplay.

I have a degree in Math, I'm an CS Engineer. I love sports and outdoorsy stuff.

Mostly through my life my closest friends were male. I've learned how to blend since after leaving college and males as your closest friends is just not an option.


OP here and I relate to a lot of this. I was computer programmer for years before switching to a related field.

It was actually clothes & makeup that made me think about this topic specifically.

After a long time working remotely, I'm interviewing now, and for the level I'm interviewing at, there is this expectation of looking the part. I 100% feel like I'm playing dress up and don't feel like myself at all. It's such an odd feeling and I wonder if I'll get used to it.


what are you wearing/doing for interviewing that makes you feel like this. pantsuits are a thing. makeup, i think you could do just a little and be fine.
Anonymous
Post 01/07/2026 18:28     Subject: Middle-aged tomboys
Still a tomboy.
Anonymous
Post 01/07/2026 18:25     Subject: Re:Middle-aged tomboys
I was told I have masculine energy. That has stuck with me for over two years. At the end of the day, I get along well with men, am able to have easy conversations, I'm decisive and I don't mice words. I guess that adds up to masculine energy. I also fully identify as a woman, 40DDs and all. Ha
I have started to identify with other women with the same level of energy and some are queer/gender fluid.
Anonymous
Post 01/07/2026 18:17     Subject: Middle-aged tomboys
I'm a self identified tomboy. I do yardwork including chainsaw stuff, hardwire lights, replace a wax seal on a toilet. I'm good at math and science even though that's not my day job. I have long hair, wear makeup and like to wear heels. My past boyfriends have sometimes seemed surprised at my random skills. I would love to meet a super handy man but mostly guys just have contractors.
Anonymous
Post 01/07/2026 18:07     Subject: Middle-aged tomboys
Anonymous wrote:I think you sound a bit gender neutral/asexual. Did you feel like you were repressed or not fitting in during your youth?


And here we go...
Anonymous
Post 01/07/2026 17:09     Subject: Middle-aged tomboys
I was never a tomboy growing up but I think some people view me that way now. I think as I get older, my face has a less feminine look to it. I have always dressed pretty much the same, in a lot of classics that can run unisex -- oxford shirts, straight leg jeans, crew neck tees and sweaters. I dont' look like a man but I don't go out of my way for my clothes to look feminine. Same with hair and makeup. I have longish hair and wear makeup most days but I guess it's understated.

A friend of mine says I don't look like a tomboy, I just look German. This is a good description of it.
Anonymous
Post 01/07/2026 16:56     Subject: Re:Middle-aged tomboys
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:I'm a tomboy. I have 7 brothers, no sisters. I still prefer men's clothes. I do buy men's sweaters/sweats/etc.

When I wear dresses, etc I feel like I'm cosplaying.

I've found ways to "dress androgenous" in a way that is "stylish" ... more so than sweats.

I did wear a dress when I married but the idea of a wedding dress was just too much cosplay.

I have a degree in Math, I'm an CS Engineer. I love sports and outdoorsy stuff.

Mostly through my life my closest friends were male. I've learned how to blend since after leaving college and males as your closest friends is just not an option.


OP here and I relate to a lot of this. I was computer programmer for years before switching to a related field.

It was actually clothes & makeup that made me think about this topic specifically.

After a long time working remotely, I'm interviewing now, and for the level I'm interviewing at, there is this expectation of looking the part. I 100% feel like I'm playing dress up and don't feel like myself at all. It's such an odd feeling and I wonder if I'll get used to it.


Can you do what Rachel Maddow does and put on makeup (for interviews), an impeccable suit, and a tad of hair styling? Then see where it goes, and what you have to keep up with? Good luck!



she’s like the quintessential tomboy


Really? I just thought she was a dressy lesbian.
Anonymous
Post 01/07/2026 16:46     Subject: Middle-aged tomboys
I briefly stopped my tomboy-ish fashion during college and a stint in NYC, and during another stint working in a major southern city.

But now I live in rural New England and have gone back to tomboy clothes and ways. My house reads very, very girly though. I know that younger women sometimes are confused about my sexual orientation but never say anything. Women my age and older don’t blink, probably because we were of the tomboy-not-the-same-as-lesbian era.
Anonymous
Post 01/07/2026 15:53     Subject: Middle-aged tomboys
Anonymous wrote:In some ways I was a tomboy - in that I was never into hair or makeup or Barbies and I liked to go fast and ride bikes. But in other ways I was girly - loved ballet and Broadway, museums and unicorns. I'm still mostly the same in my 40's. Maybe less with the unicorns.

It seems to me that kids now who would have been called tomboys think they're lesbians.


Similar here. I liked dolls, but never hair or make up, loved climbing trees, playing football with the boys, very active, and had (have) a bunch of brothers.

As an adult, I studied science and prefer camping and hiking to dressing up, still don’t wear makeup, etc. But I am straight, happily married to a man, will wear dresses if the occasion warrants, and like being a woman.