Help me decide WTW to comedy show

I originally considered the smart casual formula of jeans + heels + nice top and then I realized I didn't want to wear any outfit that could also be worn to work.

I combed through my clothing list and came up with this:

Floufy orange dress
White denim jacket
Black purse

I'm struggling to decide on shoes. If I don't wear boots, I will need to wear tights for warmth.

Cognac boots with bare legs (baggy on the calves/more suited for wearing over jeans)
Black heeled Fluevog boots (a bit predictable)
Black/white flat oxfords (unexpected and I would need to wear black tights so it would get halloween-ish)

What do you think? Alternative styling suggestions welcome and you can also tell me to scrap the whole outfit.

Thanks in advance.

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13 years ago

Veteran

It's just the oxfords with black tights that are giving me pause. Do you have any black booties? (Whatever happened to saying ankle boots, anyway?) Or would you consider nude pantyhose?

fern

Are those the fluevogs in the dress pic? Those boots are awesome.
Do you have any colored shoes?

Sylvie

Thank you JR and Fern.

JR: I do have a pair of black booties but the heels are too high for the walking I needed to do. My other ankle boots are all flat and rugged.

Fern: The boots in the first picture are by Eject who makes shoes that are just as cool as Fluevogs. I have two pairs of colored shoes - red and bright green. Can either of those be worn with orange?

I ended up wearing the orange dress, white dress and black purse with my black midcalf fluevog heeled boots. It probably wasn't a 10 but the outfit worked well enough.

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