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Stylish but Practical Footwear: 21 Days of Resolutions

Day 1

Coordinating my daily footwear choices during the winter involves mapping out a complicated battle plan: Should I wear the heavy-duty boots all day and look silly at work? Forgo the boots and have cold (or worse! stepped-in-slush-wet!) feet during my commute? Wear wellies and schlep my heels to work in a giant, heavy tote?

What, exactly, is the best way to stay warm and dry without looking completely sloppy?

This year I am streamlining my morning footwear deliberation into a no-brainer routine--cute waterproof boots with skinnies or tights outside and a tiny rolled-up pair of flats in my purse for later. Here are some of my favorite combos:

1. Loeffler Randall rain boots with back zip, $195, loefflerrandall.com. Just like the trademark leather boots they are modeled after, these sleek boots have a subtle, leg-lengthening wedge.

2. Rodarte for Repetto ballerinas, $425, openingceremony.us. The mesmerizing marbleized effect of these butter-soft flats makes any outfit a showstopper.

3. Steve Madden Tsunamii rain boots, $79.95, zappos.com. Motorcycle buckles and a shock of red down the back make these cool-girl boots both gritty and fun.

4. Porselli ballerina flats, $122.50,usonline.apc.fr. A rusty red pairs well with worn-in corduroys during the winter but sets off a crisp white dress perfectly after the snow has melted.

5. Women's duck boots, $69.50, canvas.landsend.com. Something about these utilitarian booties makes me want to pull them on over chunky cabled socks.

6. Lula ballet flats, $118,jcrew.com. A sunny slip-on at the office is sure to stand out against everyone else's winter darks.

7. Hunter Original wellies, $125, piperlime.com. The classic Hunter is exciting in this unexpected royal purple.

8. Bloch Classic Pearl ballet flats, $145, winknyc.com. Sophisticated and versatile--I can't think of a thing that these cap-toe flats wouldn't go with!

9. Ilse lace-up boots, $184, freepeople.com. From the chunky sole to the contrast laces, I love the details on these well-crafted Scandinavian kicks.

10. Foldable ballerina flats with travel bag, $179,neimanmarcus.com. For a pair of flats that fold up to a size smaller than your fist, these bronze ballerinas pack a lot of punch.

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