So, is he happy with the pigtails? You can also curl them into balls, a.k.a. double buns.
Encourage everything that challenges gender boundaries as much as you can. Society will push against it soon enough, even the society of other kids in school.
Yeah, the pigtails did it for him. He took them out later and ended up with flock-of-seagulls hair.
We do our best to let him explore unfettered. His current favorite shoes are essentially jelly shoes (calls them his sparkle sandals). Mostly we're trying to instill confidence in him, and so far it seems to be working.
His big sister is a great inspiration for him too. At 6, she wears her own eclectic style, rarely leaving the house without at least 3 or 4 pieces of costume jewelry on. The two of them are straight up awesome.
A place to talk about parenting.
Be respectful of others' parenting decisions.