Tomboy Angst

Some Tomboys are fine with their stereotypically masculine personalities or even thrive in it. Others hate the fact they're tomboys but have difficulties trying to change their behavior. They may try to invoke a Girliness Upgrade but this often results in Femininity Failure. No Guy Wants an Amazon is often a reason for them disliking being a tomboy. Whether they're fine with their tomboyish streak is another matter. Or maybe they're tomboys with girly streaks, and don't want to be seen as too tomboyish, and object when others call them tomboys because of their outwardly tomboyish physical appearance, despite their girly personality and girly interests, even if they also have tomboyish interests as well.

This appears often in Japanese works and is a point of Values Dissonance to many non-Japanese audiences. Due to Japanese society being very strict about gender roles, many female characters are embarrassed by seeming masculine and actively try to change it. It's comparatively much harder to find a pure tomboy in Japanese media who is fine with their behavior than it is to find in Western media, particularly American media, because most Western societies, particularly the United States, place greater emphasis on masculinity over femininity. In British and European societies, emphasis on masculinity is somewhat downplayed, so you might find some purely masculine tomboys who are perfectly fine with their very masculine behavior, and other relatively more feminine tomboys with girly streaks who criticize them for not being feminine enough.

May overlap with Stay in the Kitchen, which is about how other people treat them. If they have a classically feminine mother for extra contrast, see Feminine Mother, Tomboyish Daughter. And if the parents express disappointment in the tomboyishness, see Wanted a Gender-Conforming Child.

If a character had tomboy angst in the past, this could be why they Used to Be a Tomboy. Compare I Want to Be a Real Man, which has boys being insecure about not conforming masculine gender roles, which is very common in Western media, particularly the United States, due to placing greater emphasis on masculine gender roles.

Anime

• Makoto from Sailor Moon is actually a Tomboy with a Girly Streak, but laments how the former part tends to scare boys away from her. It's why she puts so much effort into her cooking skills.

Fan Works

• Pidge is given a case of this in certain Voltron: Legendary Defender fics, usually the ones pairing her with Lance.

Literature

• Jo March from Little Women is the most tomboyish of her sister and is often gets annoyed with the expectations of being a traditional feminine lady, despite being a Tomboy with a Girly Streak as well. Plus, it doesn't help that her oldest sister, Meg March, is considered the beauty of her family, and her youngest sister, Amy March, is more of a Proper Lady than her.

Live-Action TV

• Jan Brady goes through an indirect case of this in one episode, when the boy she likes seems to prefer the girlier Marcia to her. Later, Carol finds out he thinks of Jan as "one of the boys" and gives her a feminine makeover so he'll see her the way she wants to be seen.

Music

• The heroine of Taylor Swift's "You Belong With Me" has this, comparing her jeans, t-shirt, and sneaker-wearing self to her crush's cheerleader girlfrend.

Western Animation

• Musa from Winx Club is the most tomboyish out of the others in the first two seasons and even claims herself as one, despite having a girly side as well (before her Girliness Upgrade in later seasons), but she feels insecure that her crush wouldn't feel the same way about her and tells her friends, "I don't think Riven would ever be interested in a tomboy like me."
• In The Legend of Tarzan, Terk is a tomboyish female ape, who is often getting mistaken as a boy by certain others when she plays with her brothers, including her best friend Tantor.
• Janna from Star vs. the Forces of Evil secretly likes the color pink but doesn't want to give into gender stereotypes.