Style 911: “I Need Dressy Flats For Fall & Winter!”

“With winter approaching I’m getting into my usual fall dilemma (which I have obviously failed to solve). To be totally honest, I am relatively particular about shoes.  In the summer I wear flip flops, strappy flat sandals, toms and for work and nice dinners out, ballet flats.  I basically refuse to wear heels unless I absolutely must.  I can’t wear boots because of high arches (if I can get them on, they usually pinch my feet so much that they go numb) and this applies to almost every pair of boots I’ve ever tried on or tried to try on. My question is, what shoes can I wear to be semi-dressed up in the winter, for birthday parties, nice dinners out, or on a more casual day to work (I’m a lawyer)? You know, just for day to day, cute shoe wearing. To give you an idea of style, I shop a lot at J. Crew and Anthropologie, but don’t really get into trends too much. Please help!!!” – Emily

Girl, I’m with you. As I’ve gotten older, my foot pain has increased and my willingness to suffer through it in order to wear heels has waned. Luckily, there are a wealth of flats that are just as chic as sky-high heels. Based on the way you described your style, I’m inclined to recommend pointy-toed flats and preppy oxfords and loafers. After the jump, check out the 12 pairs of flats I found, with my suggestions for what to wear them with.


Wear them with: skinny jeans and a fun blouse, mini- and midi-length dresses and skirts, slacks and button-downs.

Style 911:

1. $89.95, Jeffrey Campbell, Nordstrom
2. $49.95, Gap
3. $105, Boutique 9, Shopbop
4. $119, Dolce Vita, Piperlime
5. $98, Boutique 9, Shopbop
6. $69.98, Steve Madden
7. $49.95, Tildon, Nordstrom


Wear them with: feminine and flouncy dresses and skirts, cuffed jeans and cozy sweaters, skinny, ankle-length pants and fitted blouses.

Style 911:

1. $71.98, Steve Madden
2. $70.35, Bass, Amazon
3. $100, UGG, Neiman Marcus
4. $112, Rachel Roy, Neiman Marcus
5. $75, Sam Edelman, Shopbop