Are you Allowed to Wear a Tomboy Look over 50?
London Jean leather pants, Puma silver sneakers, silver belt, Oliveo chambray shirt, Modalu Pippa bag, silk scarf (all own), and baroque pearls c/o Pearls Claps

Being a Tom boy was considered bad, very bad, when we were kids. Girl’s don’t do that! How often did we hear it? Now is still wearing Tom boy clothes, not growing up or menswear. This post is my personal experience with being a Tomboy in skirts and wearing a Tomboy look over 40.

In this post
  1. Tomboy in skirt as a kid
  2. Clothing preferences are about attitude
  3. Tomboy outfit over 50
  4. Top of the World Style linkup party No. 138

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Tomboy in skirt as a kid

When I was a kid, my sister and I liked to build dams in the drainage digs down to the southeast of the village we grew up in. These channels were anywhere between 1.5 ft (0.46 m) to 3 ft wide. The water depth was about a foot (0.3 m) to a bit over 1.5 ft deep. The digs were about one yard below the level of the adjacent grassland. To get into the area, we had to climb thru a fence at the side of a bridge and then walk down along a large channel. One only could cross the large channel under neath the bridge as it was channeled there to just 2 ft or so. Doing so was a piece of cake even when wearing a skirt. Then we had to walk along the trench to one of the inflows of small trenches. They were small enough to built a dam that would hold. While walking along a trench, we couldn’t see what’s on the meadows. However, someone on the meadows could see the top of our heads.

One day in fall, we came to enhance the height of a dam that we had built the day before. The water had piled up behind the dam over night. It was clear that it would spill over the dam in the following night if we wouldn’t increase the dam’s height. We were working on putting large twigs into the dig’s bed when with a sudden a man yelled at us from far behind “Hey boys, stop building dams. It’s forbidden. It will flood the meadows.” We jumped up, I jumped over the dig towards my sister to run away.

Then the guy saw that I was wearing a skirt. He realized that we were girls. He yelled at us “Tomboys, pull down the dam or I will tell your parents. You should be ashamed building dams as girls. That’s what boys do. And then even in a skirt! I will come back in 10 minutes. Then you have that damned dam down.” His voice was very angry. He then turned towards the only place where we could leave the fenced in area we were in. “How the heck did he know we were down here.” my sister asked.

midlife woman in a tomboy look with glen check blazer and leather pants

over 50 years old fashion blogger wearing a tomboy look with leather pants and a blazer
Outfit details: Tahari one-button blazer, Moda International leather pants, Puma sneakers, silver belt, Oliveo button-down shirt (all own), and baroque pearls c/o Pearls Claps


We went back down into the ditch to destroy our dam. I pulled a key stone of our construction. A big fat frog jumped right at me. I screamed and my sister jumped aside. The piled up water flew fast thru the place where the stone was before and pulled the dam down slowly. “I wonder how that frog got into the dam.” “You better wonder how we pass that man” my sister replied. “Let’s go. The water will do the rest. We’ll go over the fence at the other side. Let’s walk along this ditch with our torso and head down. So he can’t see us before, we reach the fence on the other side. That macho will not expect me climbing over the fence in a skirt, right?”

mature style blogger in chic leather coat and leather pants
Outfit details: Moda International leather pants, Cami silver leather coat, silver Puma sneaker, silver belt, Oliveo chambray shirt, shark gray Modalu Pippa bag, silk scarf (all own), and baroque pearls c/o Pearls Claps

Clothing preferences are about attitude

My sister always preferred wearing pants when she was a kid. I never saw a reason not to wear skirts when we did all kind of tomboy activities. Why was that? As a kid I had no idea and never thought about it. After I was allowed to pick my own clothes, I just wore what I felt great in my skirts and what I liked wearing.

Maybe the attitude a woman can do all things a guy can do, but in heels?

Including wearing jeans which I wasn’t allowed. Including another thing that upset my folks. It was that I wanted to wear black and leather as a toddler.

What do you think? Is Gamine Style related to being a tomboy?

Tomboy outfit over 50

Now in my fifties, I still enjoy doing things that were considered “men’s stuff” when I grew up. Science, for instance. However, I still love clothes that clearly indicate I’m a woman. I once in a while like to dress in a Tomboy look, but all pieces must clearly have a female cut. The trench coat, for instance, is tailored at the waist. So are the blazer and button-down shirt. Should women over 50 don a Tomboy look? Why not?! It’s about confidence. Sometimes it helps when you have to put your foot down.

Did you wear skirts or pants as a kid? Did you enjoy doing “boys’ stuff?” Let me know, I’m curious.

Top of the World Style linkup party No. 138

Welcome to the Top of the World Style linkup party. When you are new, welcome. We are glad you are here.

Readers, did you know you can also participate in the linkup party even when you don’t have a blog? Just linkup your Instagram outfit posts. If you don’t know how to linkup you may be excited to know that I now have a page that describes the linkup process. Check it out. If you have any questions please do not hesitate to contact me. I love to hear from you and love to help.

You can sign up to join the VIPs who receive an email invitation each week for the Top of the World Style party.

As a “Thank You” for joining the party, I will pin my favorite photo from your linked outfit posts to the Top of the World Style Pinterest board. The pinned photos may drive some traffic to your post beyond the traffic from the linkup party. You can follow the board at the link. When you are interested in contributing to this group board by pinning more photos of your outfit posts to the board or by pinning your favorite outfits from this party, send me an email with the request. Please follow my boards on Pinterest (Pinterest requirement to add you). I will send you an invitation to join the board. Then, you just have to click the accept button to start pinning.

By linking up you agree that I can use a photo from your linked up post in the case that you become the Top of the World Style Winner, Top of the World OOTD Readers’ Fav or Top of the World OOTD My Fav. Thank you. 🙂


Top of the World OOTD Readers' Fav Suzy Turner
Suzy Turner the British book author and blogger at Suzy Turner in Portugal became Top of the World OOTD Readers’ Fav. Photo from her post


The thumbnail by Suzy Turner, the blogger at Suzy Turner in Portugal was the one you clicked the most. Thus, she became Top of the World OOTD Readers’ Fav. She styled her knit dress look perfectly. It looks so cozy and posh casual. Who wouldn’t love to have such a great dress for a night out?

Top of the World Style weekly fashion linkup party @ High Latitude Style @

Top of the World OOTD My Fav Kileen
Kileen, the petite blogger at Cute and Little became Top of the World OOTD My Fav. Photo from her post


Kileen’s looks with her pink coat became my favorite looks of last week’s party. She is the blogger at Cute and Little. Doesn’t she look cute in this pink coat with tan skirt and over-the-knee boots? The color combination is so cool. <3

Top of the World Style weekly fashion linkup party @ High Latitude Style @

Congrats ladies! Please grab your respective featured Top of the World Style button for your sidebar, featured or awards page. :).

Get free promotion for your linkup party

When you host a party, please send me an email with the day, name and your blog URL. I then will add you to the linkup directory. It’s free!

Now let’s party. Everyone of any age and gender is welcome to share their fashion and style posts.

Top of the World Style linkup party logo

  1. I would highly appreciate your linking back to this post.
  2. Grab the above banner and put it into your sidebar if you like
  3. Please follow your hostess via email.
  4. Linkup up to four of your fashion/style posts by simply adding your link below
  5. Please be a good sports and visit the posts of at least three of your linkup-fellows, introduce yourself to them to network and to make new friends. If you know them all already, I am sure they will still appreciate your stopping by and leaving a positive comment. We all like traffic, don’t we?
  6. Please spread the word about the party so we all get more traffic. Share the post See the awesome outfits at the Top of the World Style #linkup party. #ffblogger Click To Tweet

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