1. Keep your feet dry
2. Keep your feet warm.
3. Provide grip in the wet slushy streets.
Frankly anything else doesn't matter. With that said, if you wish, like I did yesterday carry an extra pair of shoes and switch at the office. Or simply look for a pair that is not as bulky and you can live with wearing with whatever you choose to wear for the day. Here's an example:
Cole Haan Air Rhone Quilted Boot from Mr. Porter for $54 shipped
There is nothing super spectacular about the boot but it meets the 3 requirements, which is all that matters. Thankfully they aren't overly bulky in the toe and I can wear them with jeans and a simply white or gray shirt or sweater and black coat.
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