How to Wear Black Leather and Stilettos to Work

districthilo1An easy way to step up your work outfit game and get more mileage out of fun weekend pieces is to wear your black leather jacket and stilettos with a conservative dress. districthilo3  districthilo2 districthilo4I teach at a university in the DC area, and the atmosphere is so collegiate casual. I’m sure you can imagine the sweatshirts and PJs at 8:00 am classes, right?

While I do appreciate being comfortable, I prefer not to go so relaxed most of the time (except maybe during finals when I’m power grading).

I recently wore this look to work and felt put together but comfortable the entire day. I love the combination of gray and black together, and this leather jacket and tall black pumps lent a slightly more hip edge to the outfit.

I topped it with a gray plaid scarf, which thanks to Burberry just never seems to go out of style.

Work attire is tricky, I think. It’s easy to fall into a rut on busy workdays and throw on the same predictable things everyday. What do you wear when you’re trying to step things up at work? Let me know in the comments!

Outfit details: Leather jacket: Halogen, Pumps: Charles and David, Dress: Maggy London, Clutch: Coach, sunglasses: Valentino If you like this point, please like it below and follow my blog, instagram, or pinterest accounts! Thanks as always for your support… I really appreciate it!

26 thoughts on “How to Wear Black Leather and Stilettos to Work

    1. Hi Natassia,
      Thanks for your comment! I’m surprised that Dutch universities are caasual… I always thought Europeans as being more formal than Americans in dress all the time. In fact, I think US universities are pretty laxed. Most of my colleagues probably wouldn’t dress this way… but I personally like to go a bit more dressy.

      Liked by 1 person

      1. Well, the Dutch are casual and don’t like hierarchy. The Germans however.. they are very formal. So there are quite significant differences even though the German border is fewer than 160 km (100 miles) away from my university. 🙂


      2. Yes, I can imagine the difference between Dutch and German styles! I think overall faculty in US universities also don’t like hierarchy. It’s actually the perfect job for me because it offers so much autonomy and freedom in research and writing. Of course, it’s loads of work too, but I’m okay with that. I just don’t prefer a typical 9 to 5 schedule.


  1. Hello Mary! How cool is that you teach at an University in DC! You must be super smart! I love wearing dresses to work. To step it up I wear heels and a blazer or leather jacket and to step it down I wear flats and denim jacket or vest. You look beautiful wearing that super chic leather jacket with the scarf. Wishing it was a little cooler here in Florida:-( Have a wonderful weekend! XOXO, Jeannette


    1. HI Jeannie!
      Thanks for your sweet comment! I teach English… languages are my love! And it’s so great that you also publish your blog in Spanish! I love that!


    1. Hi Kathy,
      Thanks as always for stopping by! Yes, it’s important to be comfortable at work. The dress and jacket are super comfy… the shoes not so much. But thankfully I don’t have to be on my feet all day.


    1. Hey Yvonne!
      Thanks for such a sweet compliment though I’m not sure the students think that… one student once wrote in my reviews that I wore “funny outfits”!


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