Style Advice Q & A

What to Wear With Black Mary Jane Wedges?

Hi Deborah,

What do you think of Mary Janes, and what can I wear with black Mary Jane wedges? Thanks, Helen

Hi Helen,

I can’t say I’m a big fan of Mary Jane-style shoes because they can look quite “school girl”  for a 40+ gal. They were originally designed for children, and bring back memories of kindergarten. However, I’m a big believer in wearing whatever makes you happy, and I understand that comfort is often a priority. There’s no denying that Mary Jane shoes for women are growing in popularity, especially since many of us are starting to have foot problems. The good thing about this is, that we’re seeing more varieties of Mary Janes, some of which look more grown-up.



How to Pick the right Mary Jane Shoes

If you are going to wear this style, go for a high-quality shoe like these black Mary Jane Kimona Wedges by Mephisto.  I like them because they’re:

  • Well made
  •  very comfortable
  •  Finer looking than many of the clunky, masculine-looking Mary Janes out there.
  • Narrower at the toe, not as rounded as some, which makes them look more grown up.
  • Suede, which is softer and more elegant than shiny black patent Mary Jane shoes, which can look juvenile.
  • sensible, but not ugly




What Should You Wear With Mary Janes?

I find Mary Jane’s look best worn with straight leg or bootcut pants. Wearing them with very skinny jeans pants that are tight around the ankles, or with capris makes it look like you have duck feet. Black or dark pants will make them blend in and create a nice slimming line. Since they are more practical than fashion forward, I’d put the emphasis above the waist by wearing a beautiful colored or patterned top.

Can You wear Mary Jane Wedges with a Dress or Skirt?  

Mary Jane’s shoes are casual, heavy-looking shoes that look best with casual dresses and skirts. They look really good with knit dresses because the weight of the dress balances the weight of the shoe. They are too casual and heavy for a dress that is very light and airy or a dress that is very sleek and tailored like a sheath dress.

The best type of hose to wear with Mary Janes are semi-opaque or opaque tights. Sheer pantyhose are too fine and elegant for such chunky, casual shoes.

How Do You Keep Your Look Grown-Up?


Be mindful not to wear Mary Jane wedges with anything too frilly, ruffly, or sweet because it only emphasizes the little girl look. Keep things sleek and sophisticated all around, so the shoes look more classic and blend in.

Here are a few more women’s Mary Jane shoes that are more on the refined side.  The ones with the double-angled straps give the shoe a more sporty look.


What are some other flat or low heel daytime options besides Mary Janes? …You can’t go wrong with a ballet flat or a classy wedge with no strap. They work with everything.


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6 thoughts on “What to Wear With Black Mary Jane Wedges?

  1. I have two pairs of Naturalizer brand mary Jane that are very stylish and comfy. They have thin soles and don’t have the heavy look of the two styles above. I wear them in both pants and skirts.

  2. Kudos for recognizing foot problems as we age. If only manufacturers would (at an affordable price). Second, Mary Janes have never been a fav of mine, Prefer ballet flats or the “new” trend of ghillies, which by the way, are a take-off of Irish dancing shoes! I also gravitate to flat-heeled boots.
    Something those of us struggle with in cold, snow states is that any open area in a shoe will invite rain, slush, or snow. Far too often, we go from 84 degrees to 34 and rotten. Just one more reason I will not invest in shoes of this type for Fall/winter wear.

  3. I am not a fan of Mary Jane-style shoes. However, I have seen much worse. I noticed a fashionable woman wearing them in the winter while shopping. She wore them with dark tights and a slightly above-the-knee cord skirt. A fitted cardigan topped the look off. I thought she looked great and comfortable.

  4. In response to Julie’s comment that chic shoes are not “Available in the specific, specialty size I need (for example, I wear a size 8 AA width shoe. Hardly anyone but the “frumpy specialists” and athletic shoe makers make those.)”, I have to disagree!! Just do a web search for sites that carry narrow-width shoes: has links to several. The Zappos site alone has 25 pages of AA-width shoes in women’s sizes in every kind of style.

    My shoe size is 8AA with an AAA width heel (good luck finding much in that size combo, although they do exist!). I’m currently wearing a pair of Charles David pumps in size 7.5B, which fit like a glove: I find that European shoe brands or styles generally include much narrower than North American ones.

    While I can’t offer any insight on individual foot pain or comfort since those are so subjective, I have to agree with the Glam Gals – the Mary Jane wedge looks unflatteringly like something a schoolgirl would wear, and there are more flattering, comfortable, supportive, options.

  5. While they “scream high school,” good quality Mary Janes are among those few shoes that those of us with foot pain problems can often turn to as a shoe that is comfortable and offers proper foot support. And it’s also one of the few styles we can wear with dresses.

    Some of us wear things that seem unfashionable or “woefully clueless” because they address or prevent a problem that the “chic stuff” doesn’t or can’t. I’d love to wear “chic shoes” at all times. Still, the reality is that few of them are a) Comfortable, b) Good for my feet, or c) Available in the specific, specialty size I need (for example, I wear a size 8 AA width shoe. Hardly anyone but the “frumpy specialists” and athletic shoe makers make those.)

  6. Thank you, Deborah! I forgot that my Mary Jane wedges are backless- you could call them mules. Anyway, I appreciate your advice & I will wear them with pants!

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