Dear Dana,

My husband recently bought me a pair of black leather boots with a shiny finish and a serious stiletto heel. I’m delighted to find I can somewhat walk in them! How can I incorporate these into my wardrobe? Are they okay for business or are they strictly casual?

What a great gift! A question for you… are the boots patent leather? Patent leather has a high gloss, mirror finish. Very chic right now.  Whether they are patent leather or have a glazed leather finish, you can easily work them into your wardrobe. As long as they don’t have heavy detailing such as heavy chains or heavy buckles, they can be worn with almost anything except a very traditional business skirt suit.  Another point of consideration–if you’re doing a presentation (and they are indeed patent) you’d want to avoid wearing the boots with a skirt or dress. The shiny finish will be distracting to your audience.

How to showcase your new boots? They would be super cute and modern with a wrap dress. They are a natural with skirts—almost any style as long as it’s not overly casual. Certainly they will work well with nice black pants. The caveat here is that your pants must be very long. Since you mentioned that the new boots have a serious stiletto heel, your current pants may need to be lengthened, or you may need to buy a longer pair to accommodate them. Your slacks should only be ¼” to 1/2” off the ground. Wearing your pants long like this will make your legs look a mile long! Lastly, because patent leather was originally considered a formal material, your boots would even be edgy with cocktail attire.

Have fun with your new boots!