I’m a teacher at an all-girls high school. I need a pair of low-key heels to wear to prom, graduation and a family wedding this spring. It’d be good if the shoes did not b...

I’m subjecting myself to a “speed date,” where you spend five minutes each with 20 different people, trying to decide who you’d like to see a second time for a real da...

We’re just three weeks into the new year, and I’ve got the doldrums. Maybe it’s the weather; maybe it’s the let down after the holidays; maybe it’s that I’m stuck ...

I’ve been promoted to detective after almost a decade as a patrol officer. I’m happy to be rid of clunky, black cop shoes but stumped as to what would look good with the s...

I’ve been searching for the perfect pair of black booties for what seems like eons now. I’d love a walk-able heel (I live in Toronto and walk a ton) but nothing dowdy. I'm...

Now that all my Christmas shopping is done, I can address finding a pair of shoes to wear on New Year’s Eve. My husband and I are going out with some people from his office ...

My semi-serious boyfriend of five months has asked me to come to his parents’ house for dinner on Christmas Day. I met them once before, and I don’t think it went so well,...

I walk at least one mile (sometimes two) every day between buses and Metro stations. When it snows, my flats aren’t good enough, but snow boots are often too much. What sort...

For Christmas, I’ve been looking to buy my little sister, who’s a first-year student at a university in the upper Midwest, a new pair of winter boots that she can wear aro...

I’ve got Thanksgiving duties this year, which means I’ll be feeding 25 people, maybe more. We like to dress up for the meal, and though I’ll be able to change at the las...

I’m just about to turn 50 years old. I keep myself in good shape, and I think I still look great, but I am somewhat depressed by passing the half-century mark, so I and need...

This past weekend’s early snowstorm made me realize that I need to get going on my winter wardrobe. I need some new winter boots, preferably not black. I find that when I dr...

I am planning on showing solidarity with Occupy Wall Street this weekend, and I am looking for a shoe that shows I am “of” the 99 percent, yet is stylish enough to be worn...

I would like to find some black sneakers that I can walk and do tai chi in but that still convey a modicum of chic. Is it possible to be chic in sneakers? — Katie Manolo say...

In mid-November, I’m attending a wedding in Montreal. I already have two pairs of shoes for the ceremony and the reception picked out. However, I need something both stylish...