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Another fashion question about shoes.


Night Elf
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I wear Toms Classic Slip-ons when the weather doesn't call for socks, and Keds shoes when it does call for socks. I'm simple. 

 

So now I'm trying to update my wardrobe and I have 3 wonderful skirts, all ankle length. I've been wearing Toms with them and I think it looks okay. However, I would really like plain black shoes to wear too. Should I order a pair of black Toms or go find leather flats? I dress casual. I'm wearing tshirt material with my skirts.

 

And then what do I wear with my skirts when it's cold? I feel booties would look odd with my skirt. Should I get them or try to find a pair of taller boots? I do plan on wearing leggings. I just don't know if booties go with ankle length skirts.

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