"Ever stylistically paint yourself into a box?"
moi? but of course!
Especially when i was younger. But as i grew older and began to understand my style as more a manner of mixing various pieces for outfits, as opposed to relying on 'the perfect' individual pieces to convey my style, i started to find my way out of that box. Angie's approach to mixing high and low helps immensely, not just in making outfits but in creating a wardrobe. Mix up to your hearts content in the everyday - and then when you have a spiffier event to attend, just pull from the 'fancy' side of the closet.
Anna, another thing i've found is this - if you're known for your wonderfully over the top creative looks, NO ONE wants to see you at your friend's wedding in slacks!!!! They're all looking forward to seeing what you come up with, and i tell you many of the people will see that as one of the day's high points. So i would, fwiw, counsel appropriateness to the weather and any activities (ie. shoes you can walk in) but i would not try to 'fit in' overmuch.
Which gives me an excuse to play in your virtual closet
First idea is kind of a proper, ladylike toreador getup.
Skingraft sculpted shouldered leather jacket
Club Monaco cropped, pleated pants
unidentified white shirt which would go with the Zara pearl and rhinestone collar
Hair twisted up both sides at the top like in this post (maybe a little flower in there?)
sexy pumps - blue leopard or black sequin
Second idea - very easy, casual ultra glam:
sequin encrusted silver-gold 'tee'
worn over flirty black tulle skirt
I see the hair in a big messy french twist, nicely groomed and arched brows, 'naked' mouth (you could even go '90's naked!) and a bit of smoky eye (i think it would look more modern and softer than a cat eye, the obvious choice with this look. Also the cat eye could easily get messy).
sky-high black sequin pumps to show off your killer calves and ankles - yowza anna! (okay, not the easiest to walk in but you could make an entrance and have a spare pair stashed somewhere - maybe in your hair?)
and a clutch or some species would be perfect, and a simple but glitzy pair of earrings.
Anyways, just a couple of brainstorms - so fun to play in your closet, as it were Hang in there, these types of events can be trying but you'll look fantastic, your fans will adore you, and you will have a blast! Happy Day, stpeh