Headscarves: the cute, the sickly, and the culturally appropriated

So I've been into the idea of having a headscarf look. I mean, right?

But tying a scarf around your head is not as intuitive as you might think.

And I'm not into the "I'm hiding my head while I'm sick" look. Though sometimes the same scarf can look boho-chic.

I took this one off the mannequin at XXI already tied. On the mannequin it looked bold and awesome. On me?

I look like a hippie at a fracking renaissance festival. In 5" stilettos - Jesus.

And finally I found one I like. My friend Samantha tied it for me and it looked so pretty. that was until my friend Christina goes "OMG YOUR HAIR IS LIKE STICKING OUT OF THE TOP. EW! THAT LOOKS GROSS." Gotta just love her. But the more I moved - the worse it got. Dealbreaker.

Then I went to TJ Maxx (in Manhattan - crazy right?) and tried on ALL their scarves which were on super clearance because it's summer. But there's a reason I didn't buy any.

Some were cute- ish. I found a short scarf and tied it like a headband. Then I used a silky blue dotted scarf to fully cover my head - though the fabric made it kind of a mushroom hat shape. Then I found one of those half-scarf, half-necklace ones (that was intact - these break SUPER easily)...well not so cute. Oh well.

But others gave me a weird sense of cultural misappropriation. Especially when an older black woman came up and started asking how I had wrapped them, admiringly. I loved the chevron infinity scarves, the layered effect (pink) may be too much. And the blue Calvin Klein scarf had amazing fabric.

I just can't imagine wearing any of them, as pretty as I think they are, without feeling like I'm stealing from another culture. Am I nuts? Am I being racist by thinking that? Does season have anything to do with it? Will this look be more acceptable in the winter? Are any of these professional enough to keep me warm in the office? Do I have to match scarves to my dresses?

PS: Apparently my microcephaly (mentioned in my Wig Post) is great for infinity scarves - they fit perfectly. But you can always tuck extra fabric! And these are surprisingly easy to wear and keep in place.