It`s in My Closet, Now How Do I Wear It?: Square-Toe Ankle Wrap Mary-Jane

The Item/The Dilemma: I bought these shoes in 2001 at Steven Alan. The line is T29. According to the box they were $262. I think I must have gotten them on sale. I am too cheap to spend that kind of money. Anyway, I think I last wore them in 2001, yet they have survived many closet purges. Maybe because of the square toe which is allegedly comfortable. Yet somehow not. And I feel they evoke bondage too much for a suburban mother. Thoughts? Christina

I can see why you wouldn`t want to part with these shoes after 10 years. There is something strangely alluring about them. The mix of the deep toe-cleavage and the kitten heel is like a Victorian shoe that was all, “Screw these prudes, I`m outta here!” (This is a good thing.)

Now let`s go over what concerns you about them:

Square toe: The square toe gets a bad rap as “outdated” but I think that only counts for men`s shoes so who cares. I think the deep cut on the front, with the aforementioned toe-cleavage, is really what makes these shoes so special. Like it`s secretly inspired by a ballet pointe shoe.

That bondage feelin`: I don`t think they are bondage-y but I think that`s an automatic effect of strapping anything that`s black leather around any part of your body. An easy way of remedying this is to wrap the strap around your foot as opposed to the ankle so it looks like a multiple-strap Mary Jane that you could probably pass of as “some weird Japanese designer.” (Although they COULD be some weird Japanese designer, Google wasn`t very helpful with giving me the 411 on T29.) If that isn`t feasible, then maybe just wrap the straps below the ankle closer to the shoe and it`ll also tone the bondage-thing down a vibe.

The Solution: In terms of outfits, I would probably pair them with clean-line skirts and dresses, and they`ll look really cute with tights as well. I don`t know that I would pair them with leggings because it might skew a little too mall-youth, BUT I would approve of those footless tights that dancers wear that cover half the foot or whatever (show that toe cleavage!). It might sound a little crazy but if you`re feeling adventurous, give it a whirl!

They would also look great with a slim trouser that was cropped right above the ankle. The bit of skin between the shoe and the hem of whatever you`re wearing is essential.

I hope this helps! Send me an outfit pic if you ever end up leaving the house in them.

Got an item you keep hanging on to despite having no idea how to wear it? Send a photo and description to laia@janepratt.com for help.