Everlane Day Buckle Mary Jane vs Everlane The Boss Boot

Buy the Day Buckle Mary Jane for an easy, low flat you can walk in all day; buy the Boss Boot for a structured ankle boot that dresses up an outfit. The Mary Jane is soft nappa leather with an 8mm heel and a round toe, and owners call it comfortable out of the box, though many say it runs small and narrow and the toes scuff fast. The Boss Boot is a pointed-toe stacked-heel boot with a side zip; it fits true to size and looks more polished, but the pointed toe and 2in heel make it a worse pick for long walking days.

• Choose the Day Buckle Mary Jane if you want a soft, low, round-toe flat for casual wear and travel and you can size up for a narrow fit.
• Choose the Boss Boot if you need a pointed-toe ankle boot with a stacked heel for work or dressed-up outfits and want a true-to-size fit.