Comfortable Women's Dress Shoes

Knowing what shoes to wear for professional, dress, and casual-dress occasions is easier than ever as more comfort manufacturers enter the women’s shoe market.

The basic styles are the

  • classic women’s pump
  • Mary Jane
  • slip-on or loafer type
  • lace-up.

Classic Pump Works with Professional Suits, Dresses, and Skirts

Classic Pump Shoes

The women’s pump is a simple slip-on with a rounded vamp and any height heel.

The vamp is the most visible part of the shoe covering the toes and front of the foot.

The most comfortable women’s dress shoes will have a heel height of two inches or lower.

Other variations of the classic women’s pump are a square vamp, a V vamp, open-toes, and even the sling-back.

When you are wondering what-shoes-to-wear, the classic pump is a perfect choice. It goes with skirts, dresses, and dressier slacks.

You cannot go wrong with a classic pump. The selection of extremely comfortable shoes for dress and business wear is widening briskly.

Ballerina Flat May Be Worn Dressy or Casual

One variation of the classic pump is the ballerina flat, a pump with almost no heel height.

The small tie at the front of the typical ballerina flat, mimicking the tie on actual ballet dance slippers, illustrates the embellishments that may decorate a women’s pump.

Bows, grommets, and contrasting trim may add visual interest to the classic women’s pump.

Some of these, such as bows, may be clipped on by you to change the look of the shoe. Hair accessories may work, and crafty gals may design their own.

Bows, rhinestones, and the like do not dress up plaid slacks and shorts or Capri-length slacks. They suggest that the wearer does not know what-goes-with-what.

On the other hand, a plain ballet flat goes with almost everything, and its understated elegance keeps the eyes focused on other costume elements.

If you wear diabetic orthotics, here are some suggestions for diabetic dress shoes.

Are Sling-Back Shoes Business Appropriate?

If you want comfortable women’s dress shoes, the sling-back is a questionable choice. This style replaces the back of the shoe with an adjustable strap, usually with a buckle and elastic.

Elastic is prone to stretch. Then, the straps slide down on one’s hose. I have to bend down to reposition the straps frequently, sometimes after walking only a brief distance.

I wouldn’t want to flee from a possible attacker wearing these.

Open-Toes Shoes Open Employers to Workplace Injuries

Open-Toes Shoes

As for open-toe shoes, my feet slide down, and the opening pinches.

Employers usually prefer that women wear closed-toe shoes for safety reasons. Imagine dropping a toner cartridge on your exposed feet!

The more formal and expensive your work environment, the less appropriate are slingback and open-toe shoes. Do not wear these to an upscale law office, court, or employment interview.

Open-toe and sling-back shoes are flirty and feminine, and this is not the image to project as a mature woman at work.

They are fine for dressier occasions.

Each of us, however, has uniquely shaped feet and comfort needs. You have to decide for yourself if these style options are for you.

Mary Jane Shoe Is Perfect with Everyday Dresses, Skirts, and Pant Suits

Many formerly athletic shoe manufacturers — such as Timberland and Merrell — are now manufacturing Mary Janes as they move into the women’s dress and casual shoe markets.

The Mary Jane has a dainty, feminine look. The stylish strap is a design element that conceals the extra attention to fit provided by the cross-strap.

If you are wondering what-shoes-to-wear with everyday dresses and skirts, the Mary Jane may be worn for all but the dressiest occasions.

You also may wear the Mary Jane with long slacks that conceal the strap. Then they look like classic pumps.

When Not to Wear A Mary Jane Shoe

Most of the time, we would not wear a Mary Jane shoe with a chiffon ball gown or a sophisticated little black dress.

You may be able to hide the Mary Jane beneath a very long evening skirt or full palazzo-style pants. In a pinch, we can — in the words of fashion guru Tim Gunn — make it work.

The Mary Jane also is serviceable when worn with a pantsuit, so long as your pants are long enough to have a break.

Definition of “The Break” in Slacks’ Line

The break is a tiny fold where the front of the slacks meets your instep. This naturally hides the strap, so only the smooth vamp appears outside the slacks.

Slacks with a slight break is a more professional look and create a long, lean line that flatters most figures. It is not professional to show socks and ankles between the top of the shoe and the slacks’ hem.

The break, a term I am borrowing from menswear, is not a dreadfully rumpled bottom that needs to be hemmed.

An appropriate break may be achieved if the pant hem meets the place where the shoe upper meets the heel. This length may need to extend slightly past that seam if you are wearing a higher heel or 1.5-2.5 inches.

I like to fit my slacks for a relatively low-heeled shoe. Then, if I switch to a 2-inch heel, my ankles still will not show. The front of the pant will brush or nearly brush the top of my foot.

If you have attractive, well-shaped legs, the Mary Jane is versatile enough to wear for more casual occasions with shorter slacks and even with Capri pants.

Comfortable casual shoes come in a wide range of styles, including women’s lace-up shoes, slip-ons, and clogs.

Buying Shoes Online Offers Variety and Convenience

Now that you know what-shoes-to-wear for business and everyday outfits let’s consider the opportunities for shopping online.

I started pampering my increasingly happy feet some time ago. Finding comfortable women’s dress shoes locally may involve endless driving, only to discover a style I like that’s not available in my size and is no longer in production.

Ordering online shoes save me lots of time and frustration.

Naturalizer offers an incentive to shop online with exclusive offers available only on the web. I have at least two pairs of Naturalizer flats that offer good comfort and value for the price.

Free Shipping BOTH ways on Shoes at!. So far, I have not encountered any unadvertised return shipping charges for shoes at Zappos — but such policies can change at any time.

In addition, Zappos has complete descriptions of the padding in comfortable women’s dress shoes and product reviews by customers like you. even has a glossary of shoe-related words, such as vamp and slingback. Just type “glossary” into the search box on the home page.

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