How to Wear Tall Boots to the Office

How to wear tall black boots after 40

Lisa looks great in a pencil skirt with boots which keeps her warm.

Deborah BolandYou’re off to the office but need to stay warm.  Here is a simple idea on how to wear tall boots to the office from Etiquette expert Lisa Taylor Richey and it’s easy as 1,2,3!

Lisa says:

1. Choose a dress or skirt 

2. Next you will need a pair of opaque hose

3. Toss on your boots

Now, you will be toasty warm and still look  professional.

Of course there are always exceptions to the rules…  First, know your company culture and office.  If you have doubts, usually the answer is “no,” don’t wear the boots.  However, most offices these days are not that formal so by adding a good pair of simple, basic boots you will be able to stretch your current wardrobe.

Here are  some do’s and don’ts on how to stay professional but warm when you’re heading to the office or meeting a client:

Tips for Wearing Boots to the Office

  1. Start with a pair of opaque tights; great for warmth and more comfortable than pantyhose.  Sheer or nude hose don’t work because you need some “weight” to your stockings to help balance the bulk of the boot.
  2. Boots with your slacks is a yes! (just don’t “tuck” them into your pants for the office)
  3. Do keep the color of your boots to black or brown.  Stay conservative.
  4. Keep the heels polished and clean.  Take last years boots to a shoe repair if heels look worn.
  5. Don’t wear over-the-knee boots to the office, they are not age appropriate or professional.
  6. Don’t wear short skirts with boots (skirt length should at least be at your knee or below).  The young girls can pull it off; after 40 it’s a big “no, no!”
  7. Don’t wear boots with really high heels (3 inches is the perfect height for the office)

How to wear tall black boots to the office

  What do you look for when buying a pair of boots for your work wardrobe?  Please leave your comment below:

Lisa Taylor RicheyLisa Taylor Richey is a business etiquette trainer and speaker.

She is the founder of The American Academy of Etiquette. 



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Comments, Feedback, & Opinions:

  1. Are ankle-length boots appropriate for office wear.. I have a one in camel and would like to know if it is apt for a office wear..

    • Hi Neha, It depends on 1) how conservative your office is and 2) the style of bootie. Choose a sleek, streamline bootie over a rugged bootie that may be distressed, or an edgy bootie with too much hardware.
      In casual offices you can get away with more, but in businesses dealing with finance and accounting you would want a very elegant bootie that almost looks like a shoe and you’d want a dark bootie with dark matching hose. Hope that helps. Cheers, Deborah

  2. Carol McKennon says:

    I’m not sure short skirts should be an automatic “no no” after forty. I have good looking legs at 56. They are one of the few body parts that are still holding up. Wearing a short skirt makes me feel young, confident and sexy. Short skirts are not for everyone but if you have the legs for it why not?

    • Hi Carol, Yes that’s a general rule. If you have great legs up to a couple of inches above the knee is fine. You just don’t want to be wearing a mini that ends at mid thigh!

  3. deb gayowski says:

    You mentioned over the knee boots are not age appropriate at the office. What about in a casual setting? I have a grey pair of nine west boots with about a 2 or 3 ” chunky heel that I didn’t wear last year because I was worried about whether or not they were in fact age appropriate. I am toying with getting them shortened, but am worried it may ruin them. I am 56. What is your verdict on this one. I am still sitting on the fence!

    • Hi Deb, You can certainly wear them in a casual setting. Do not try to shorten them, you are right it will ruin them. Enjoy and have fun in them..they can be sexy and hip!

      • Deb, get off the fence. I too have a pair of black otk boots (Sam Edelman..so cute) and I went through the same angst as you with regard to wearing them with jeans/jeggings etc. I must agree with Glam Gal Deb on this one, wear them! Just remember to “own” the look, everything looks better with confidence. By the way, don’t be surprised at all the compliments you and your boots will receive.