What to Wear III: Shoes! Shoes! Shoes!

Dear Amy,

I have the most glamorous classic outfit to wear this Christmas (with a retro top just for that pizzaz) The thing is I have my hair and make up and out fit all figured out….but the SHOES are making me insane. Normally I would just wear black peep toe heels, but because I got a pair of those lovely winter white slacks to go with my black little cocktail jacket I am not sure that black would say “Classy” so much as “TRASHY”!!!
What do I do? I mean, no one who will be there will really give a rat’s ass, but it is so important that I look and feel okay (Like I was the one that knocked it out of the park, again.) that I need your help.

Thanks,
Shoeless in Seattle

Hooray for shoes! And hooray for over-thinking!

Black shoes are FINE with this outfit. Not trashy, like say, five-inch fire-engine red patent-leather peep-toe platforms would be, or a pair of bedazzled resort-wear thongs. Those would be a little trashy.

So yes, your black peep-toe pumps should be just lovely with this, provided the heel isn’t too high or low for the pants AND that you’ve had the pants hemmed (if necessary) to avoid the unfortunate HALP! MAH PANTS BE EATIN MAH FEETS! look. Patent leather would look especially hot, if you’ve got ’em, and would set off the sequins on the shirt. You do NOT, however, want to go overly matchy-matchy, so avoid shoes in similar fabrics (like say, brocade or anything shiny like satin). Beading or other bling could be okay, provided it isn’t exactly like the trim on the shirt. Perfectly matching shoes don’t generally look awesome as you might think — they tend to look a little OCD and blah, actually.

If, after much mirror-prancing and more over-thinking, you still don’t think the black shoes are quite right, you could try a gunmetal or pewter metallic shade. (Basically, look at the bracelets paired with your shirt online, and aim for that color.) Maybe something like this or this or this. The slightly off-black color will be a little more interesting than basic black, but wouldn’t make everybody’s eyes zoom in directly at your feet, like I’m thinking a red or super-shiny silver shoe would.

If you go with an open-toe shoe, however, TOTALLY go for some bright red polish. You’re all glammed and classed up everywhere else, so indulge your inner bad girl with a little Streetwalker Cha Cha Red polish.