How to Wear Tall Boots to the Office

Are tall boots off-limits to wear to the office? The answer depends on where you work and the corporate culture. Here are some do’s and don’ts to look professional in tall boots when you’re heading to the office or meeting a client:

The general rule is, the more conservative the office, the less likely tall boots are appropriate. In a formal workplace, they are just not acceptable. However, in a  more casual workplace where things are less buttoned-up, but you still want to look polished, tall boots can look quite acceptable, so long as you do not wear them with a very short skirt.

Paired with the right outfit, like a classic dress or a conservative skirt and top, tall boots can be just fine as casual business wear. Here’s a look at a few general guidelines to help you know what to look for:

Tall Boots with plaid floral work dress


1. Choose a Classic Boot

A clean, elegant boot with not too much hardware or that does not have too much hardware or gimmicky detail like laces; studs look most professional.

2.  Conservative Colors Rule

Colors like black and brown, and taupe are best for business and command authority.

3.  Avoid Shiny Patent Leather Boots

Save them for after work. They’re too “pretty lady.”   Also, snake print boots are too edgy for the workplace.

4. Quality counts

Leather or suede is rich and classy.

5.  A Low to Medium Heel is Best

Best to do no more than a 3 1/4″ heel. A chunkier heel is less sexy than a thin heel, but a thin heel can work so long as it is not too high, and you wear it with something conservative. Remember, the skinnier, the higher the heel, the sexier you will look, and you don’t want to look like you are going clubbing. Tall Boots - Black Pencil Skirt

6.  Hosiery Can Make a Difference

Semi-opaque or opaque tights help balance the weight of the boot, especially if you are wearing a skirt or dress in weightier fabric or a knit- such as a sweater dress.

7. Stay clear of very tall, over the knee and thigh-high boots

They’re for after-hours and are not professional for business.

8. Keep your boots polished and clean

If you want to wear boots to work, they must be in excellent condition – polished with no scuffs.


Tall BOots - Print Neck Tie Dress


9. Don’t Wear Booties with Fur Embellishment

This is too much of a fashion statement for the workplace and a distraction.

10. Avoid Short Skirts with Tall Boots

Skirts need to be just above the knee to just below the knee to look appropriate.

Tall Boots - Ponte Leggings

11.  Leggings are Generally Out

Lightweight, spandex leggings (like the kind you wear around the house or to the gym) aren’t appropriate for business casual. However, in some cases, thicker, more structured Ponte leggings or skinny leg trousers can be worn tucked into flat boots and worn with a blouse or sweater and a jacket.   Never wear regular dress pants tucked into any tall boots. You will get that baggy at the unprofessional knee look.

12.  Flat boots are Fine

Flat boots are more casual than boots with a heel; however, make sure they are not distressed or too casual looking. They should be very polished looking.

Do you wear tall boots to work? Why or why not?  Please leave your comment below:


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14 thoughts on “How to Wear Tall Boots to the Office

  1. I love to wear boots and high heels. But some of my shoes are tall. I work in a casual dress corporate job. I was just wondering.

    1. Hi Amy, If the dress code is a casual workplace and your boots are classic in black or brown leather or suede, you should be fine. Ensure your skirt is not too short, or the shoes don’t look sexy- i.e., lots of hardware or very high skinny heels. Cheers, Deborah

  2. Yes, I wear tall boots to work; living in New England, they are a practical way to wear a dress or skirt in the winter and not feel like you have to do a Mr. Rogers shoe change routine. I wear black or brown leather with a mid-size heel and matching tights.

  3. Hi
    I got a job at the bank and am confused about what to wear. I have below-the-knee boots in black, and it is winter now with snow. What kind of dress pants should I buy and how would I wear them? Because dress pants tucked in boots won’t look professional. Should I wear a dress with those boots? The place I worked previously never had any dress code, and I always wore sneakers, so my closet needed a change. Please help. Thanks.

    1. Hi Umi, Congratulations on your job. I think you are wise not to wear long pants tucked into tall boots. It’s not in fashion and also not a flattering look. Try wearing tall boots with dresses and short booties with pants. There are lots to choose from but be sure to go with a lower, thicker heel if you are standing all day. Take care!

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

    1. Hi Neha, It depends on 1) how conservative your office is and 2) the bootie style. Choose a sleek, streamlined bootie over a rugged one 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 a dark bootie with a dark matching hose. I hope that helps. Cheers, Deborah

  5. I’m not sure short skirts should be an automatic “no-no” after forty. I have beautiful 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 them, why not?

  6. You mentioned that 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 age-appropriate. I am toying with getting them shortened, but I am afraid it may ruin them. I am 56. What is your verdict on this one? I am still sitting on the fence!

      1. Deb, get off the fence. I, too, have a pair of black OTK boots (Sam cute), and I went through the same angst as you about 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.

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