I tkink you are right when you say it is a confidence thing. You look beautiful in this outfit and would stand out from the crowd in positive way in Scotland. I think you are just adjusting to your new life in Dubai and in an attempt to fit in are over analysing everything.
The next time you feel bad about wearing flats again just think how you would feel if you fell carrying Thea in 4 inch heels.
There may be subtle differences in how the other mums dress and I am sure in time you will be able read those differences and incorporate what works into your style.
Personally, I am finding it hard to adapt my style after having my babies and you have the added pressure of another country.
I am sending you hug across the web and hope you receive it.
Julie (Mum to Teah Rose and Emmy Joan.)