Q&A: How to Match Shoes with Work Clothes

December 16th, 2008

Q: Can Omiru provide some basic guidelines about pairing work shoes and pants/skirts?

How to Match Shoes with Work Clothes
Shoes with Work Clothes, courtesy of The Sartorialist

by Colleen Geary, fashion stylist and image consultant

A: To understand how to pair shoes with clothes, you first have to look at silhouette.  Shoes should complement the lines and proportions of an outfit, particularly the bottom that you’re wearing.  We’ll start with the basics—regular trouser pants and a knee length skirt—and then we’ll expand out into other options:

Regular Trouser Pants
For regular width trouser pants, the classic choice is a medium height (approximately 2” tall) shoe.  You can wear pumps, loafers, two-tone shoes…and you can also experiment with different toebox styles.  For a sophisticated look, try pointier toed shoes.  But for a more chic, casual look, you can try a round toe.  If you’re not a fan of heels, you can also try a more subdued kitten heel (usually around 1.5” tall).

Knee Length Skirts
The perfect shoe for a knee-length skirt is a heeled shoe.  Most women prefer to wear a medium height heel to visually elongate the leg, but a shorter kitten heel is also a common choice.  Women who are blessed with extra long legs can also get away with flats, but the rest of us should steer clear of them. 

Wide Trouser Pants
To balance out the width of a wide trouser pant, you’ll need to wear a high heel (3” or taller).  The high heel visually (and physically) elongates your leg line, and it gives your bottom half balance.  If you’re blessed with long legs, you can also try a medium height heel.  But for optimal figure flattery, no low heels or flats allowed!

Skinny Pants
Channel Audrey Hepburn when pairing shoes with skinny pants.  What did Audrey wear?  Ballet flats, of course!  When you’re wearing tight pants, you want a shoe that’s not overly sexy.  So steer clear of high heels and shoes with “toe cleavage.”  The ballet flat (or even really short kitten heels) will do the trick.

Short Skirts
Short skirts are best paired with a kitten heel or ballet flat at work.  If you’re wearing a revealing skirt, you don’t want to go overboard with an overly sexy shoe.  That said, the woman in the miniskirt pictured above made the sexy shoe and miniskirt look work.  How did she do it?  She wore tights to cover up her legs (and tone down the miniskirt), and she wore a heeled bootie.  Because they provide more coverage, booties are a less risqué shoe option than an equivalently high heel.

Long Skirts
Because long skirts and wide trouser pants share similar characteristics (length and width), long skirts require the same shoe options as do wide trouser pants.  So the same rules apply: high heels are best, and no flats are allowed.

I’ll leave you with two parting thoughts on shoes: 
(1) Shoes can be the sole point of interest in an outfit by providing a point of visual interest with design or color.  This is particularly true for work clothes, which are often restrictive style-wise.
(2) Shoes do not need to match the colors of your clothes or your handbag but they should enhance your overall look.


Have a great tip about how to match shoes with work clothes? Share it with us in the comments!

Entry Filed under: How To, Q&A, Women, Women's, Women's

9 Comments Add your own

  • 1. Jessica  |  December 16th, 2008 at 6:12 am

    I really appreciate this site! Thank you very much for the shoes with work clothes article. I this link to a few friends of mine.

  • 2. Sal  |  December 16th, 2008 at 11:15 am

    Great tips and sound advice!

  • 3. Christa  |  December 16th, 2008 at 6:11 pm

    Great post… and what I would give to have that outfit on the left!!

  • 4. Anonymous  |  December 16th, 2008 at 7:51 pm

    The tips on pairing shoes with work clothes are great! I have to point out that I do not consider the woman on the right’s look to be work look at all.

  • 5. mimi  |  December 16th, 2008 at 11:49 pm

    “I have to point out that I do not consider the woman on the right’s look to be work look at all”
    Um.., yeah… but she is standing in the street so…. maybe she’s working? hehehe bad, I know

  • 6. Trisha  |  December 17th, 2008 at 2:01 am

    Glad everyone’s finding the post helpful!

    As for the woman on the right, consider it a stretch for workwear…unless you happen to work in fashion. That said, with the right sweater or jacket, it’s amazing how fast it can look (almost) work appropriate :)

  • 7. Uniform Supplier  |  February 23rd, 2011 at 10:47 pm

    Nice article from women point of view.

  • 8. Jada Lee  |  April 18th, 2011 at 10:41 am

    I love the middle and left outfit! Great post and is very helpful! (Also, what is the middle person’s jacket called? I love it!)

  • 9. Jada Lee  |  April 18th, 2011 at 10:42 am

    Also, the woman on the right’s skirt is open ( I think)

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