- Material. I would stick with either patent (shiny) leather, metallic or real leather. Anything too inexpensive (like brown leatherette) is not going to be dressy enough to wear with a pencil skirt.
- Shape. I think a thong between the toe is fine, but the shoe needs to have a substantial shape to it, meaning a strap around the ankle, or in general a lot more shoe than a flip-flop would have.
- Heel. I am a huge fan of shoes like these with a slight wedge. Not only do they look more dressed up than totally flat shoes, but I think they are more comfortable, too.
Ring: My Stella & Dot website, $49
Left bracelets: My Stella & Dot website $49 and $32
Right bracelets: My Stella & Dot website $59 and $39
2. Urban Outfitters cardigan, $44
3. Lands End cardigan, $18.99