How to Stylishly Wear Flats to Work

wear flats to work As much as we may swoon over a pair of high heels, let’s face it, it’s just not a reality for most of us.  I have all but given up on wearing them and reserve heels mainly for times where they are a must or I know I won’t spend a great deal of time on my feet. And even then I always have a backup pair of flats on hand.  I’m too old, too busy and too disinterested to suffer for fashion any longer.

While comfortable shoes have come a long way, and they are far from being the ugly clodhoppers of yesteryear, it’s not just the issue of finding comfortable shoes that can be challenging but creating an outfit that looks like the flats you have chosen to wear look purposeful and not like a frumpy, comfortable alternative.  It today’s post I am giving you some wardrobe and style tip on how how to stylishly wear flats to work.

How to Stylishly Wear Flats to Work

#1- Proportion is everything

Wear flats to work I worked with a client last month who chooses flats over heels on most days for work.  I can’t say I blame her for this.  When I looked at her wardrobe it wasn’t the flats  that weren’t working, it was how she was wearing them that was.  Unfortunately, you can’t just decide to change your shoes from heels to flats and have your wardrobe continue to work.  The proportion of the looks often gets thrown off.

I am using the outfit above as an example.  Pencil skirts, like this one from J. Crew, don’t work well with flats in general, such as the pair in the outfit above from Nordstrom.   The length of the skirt needs a heel, even if it is a small one.  Of course, all is not lost if you have pencil skirts in your closet and need to wear flats, you just have to keep some things in mind.

First, avoid wearing longer cardigans, like the style from Reiss, with pencil skirts when wearing flats.  There is too much length and everything gets dragged down.  Instead, a shorter cardigan, like this one from BOSS Hugo Boss, will create a better proportion.  The cardigan doesn’t necessarily need to be cropped, but I wouldn’t go much longer than the waist.  Alternatively, if you want to wear longer cardigans, a simple fix could also be to shave a few inches off the length of the your skirts and dresses by hemming them.  The proportion of the flats to the skirt lengths will work better.

For the rest of the looks above, I used this knit top from Theory, added a Banana Republic leather wrap bracelet and silver earrings from Stella & Dot.

#2 Going From Heels to Flats is Not a Good Idea

Years ago, I used to wear heels a lot.  As a result, the tendons in the back of my ankles were a lot shorter than they are now.  Going from heels to flats too quickly, I developed a pretty bad case of plantar fasciitis, which is a terrible pain that develops in the heels of the feet from the tendon being overstretched.  I eventually had to get a cortisone shot in my heel and received the good advice from my podiatrist to wear a small heel.

If you need to wear flats more often, but have been wearing heels almost exclusively, instead of going directly to shoes without any sort of a height, just wear lower heels or else you too will likely experience a cortisone shot in the bottom of your foot.  In time, you may be able to go to flats but you should also consider that flats aren’t necessarily the healthiest choice.  As I also learned from my podiatrist, a 1-2″ heel is better for the feet and the back than flats.  This is why so many chefs and doctors wear clogs.

#3- Choose professional flats

wear flats to work There is a broad range of shoes that would be considered ballerina flats.  Some look like actual ballerina slippers and others have more structure.  I have no problem with slipper like ballerina flats for weekends but I think they can look too casual for work.  Unless you have such bad foot problems that slipper style ballerinas are your only option, I really recommend you look for flats with a more structured sole and don’t have such a rounded toe.

As you can see in the look above, this professional look of a blazer, white button down and burgundy trousers looks way more work appropriate with the nude flats on the right from Cole Haan than it does with the softer, more casual flats from Lucky Brand.  For final accessories, I added these earrings from Ann Taylor.

Soft ballerina flats are fine if you need to do a quick shoe switch but i wouldn’t recommend them in a professional working environment as your all day shoes.

#4- Shop for clothes around your shoes

It may seem obvious, but it can be far too easy to get swept up in the idea of something we see at the store and then realize that we really can’t wear the shoes required to make the outfit look right.  I have a client who spends a great deal of time on her feet.  She works on a college campus and walks or bikes to get around.  When I was pulling clothes for her this was something I took into consideration.  Unless she could wear the pieces I was pulling with flat shoes I had to let them go.

If wearing flats is really crucial, be sure to choose clothing that supports this need.

#5- Booties and Oxfords are Your Friends

wear flats to work If shoe options feel limited because you have to wear flats, I highly encourage you to check out booties and oxfords for the fall, two styles that are incredibly popular right now.  Booties, like this pair above from Sofft, can work with pants and also work with skirts and dresses, like I styled here with a dress from Boden, tights from Merona and earrings from Evelyn Knight.  Just like booties, oxfords, such as this navy pair from Modcloth, can be versatile but look particularly good with skinny pants, like this pair from Tory Burch that looks great for the office with a wool tweed blazer, blouse from Reiss and layering necklace.

Needing to avoid heels does not have to be an unfashionable death sentence.  There are plenty of options and ways to wear flat shoes that can keep you stylish at work.

  • Mrs. Smith

    In my last position I had to wear “sensible” shoes. For 3 years all of my awesome heels sat unworn πŸ™

    Booties for sure and check out comfort brands. EuroSoft is fantastic. Low wedges worked nicely too.

    • If anyone understands comfort brands it is me. If a client doesn’t have some sort of foot problem I consider it a miracle. Brands I love are Rockport, Sofft, Clarks, Cobb Hill, Gentle Soles, Aerosoles, and quite a few brands that aren’t exclusively focused on being a comfort brand, like Anne Klein Flex and Cole Haan, can be great.
      Personally, I have been a big fan of Sam Edelman’s fit. I can stand all day in my boots, but that might just be because they work well for my feet.

      • Mrs. Smith

        Yes! Sofft is part of EuroSoft or vice versa??

        I like Aerosoles a lot but the toe box is too narrow. However, if they are leather I take them to get stretched. And oh gosh I have recently discovered a love for Anne Klein shoes. I have several pair now. Ahhhh.

        I think I am just in love with shoes… πŸ™‚

        • Ooh that is a really good question, and one I should know the answer to. I will look into who owns who.

          Your comment about Aerosoles is exactly why there is no “one size fits all” answer to comfortable shoes. You can often find the most comfortable shoes from brands that aren’t designed for comfort simply because they fit your foot well.

          In regard to Anne Klein. What I love about their shoes is that they are not frumpy but are very comfortable. All too often it seems like it has to be a compromise. There was this one shoe (here is the link: ) that even my most heels averse clients swooned over. I can’t even remember how many clients bought it and loved it the second it came out of the box. I was going to feature it in my client picks recap post next week but I’ll give you a sneak peek considering you are such a fan.

          • Mrs. Smith

            πŸ™‚ Those shoes _are_ fantastic! And such a great price too.

  • agreenseaturtle

    I am very glad you are addressing this issue. I love flats. As a petite, I have to hem everything I buy. Would you suggest that the skirt be hemmed to above or at the knee break , or just below the knee or even shorter? Taller girls have more leg room to work with.

    • Of course. Just about every client I work with has some sort of foot issue. There is no definitive answer but above the knee should work. Also look at the outfits you wear on a whole. You don’t have to be an expert to know if a proportion looks okay. If something looks wonky it probably is. What most women don’t realize, however, is that even the slightest change in proportion can make all the difference. So play around with your pieces and see if hemming or even changing the length of your tops will help.

  • stacie

    I LOVE THIS POST!!! Thank you!!! For church or social, I love my heels! For work, I am on my feet way too much to be in heels, so I have to wear flats…Thank you for these great tips! I agree with Mrs. Smith- Love me some Anne Klein shoes:D

    • So glad it was helpful! Love that there are so many Anne Klein shoe fans!

  • Ivan

    Hi Bridgette and everybody,

    There are stylish flats with 1″ hidden heel that are really comfortable:

    Coach Chelsea:

    Le chateau Reflex flats:

    Sam Edelman’s Natalie low heel pump is an other good option
    If you have a really good budget Lanvin flats have also a hidden heel and are comfortable and dressy or also Tory Burch Caroline flats are a quite comfortable solution for the big pockets
    Anne Klein Petrica flats is a ballerina with a classy look, comfortable and affordable
    Hope some of this options could give you some ideas how to look dressy while being comfortable during your jobs
    Have a good day !

  • R. Ramirez

    Thank you so very much for posting this valuable information, Bridgette. Due to foot problems, I’m having to wear lower heeled footwear; and even though I work in a very casual office, the folks in the district office have instituted a dress code. I don’t mind that, except that it has been challenging for me to figure out how to dress, as I can’t wear pumps. I just ordered the Sofft Versa ankle boots that you featured in this article, as I am already familiar with the brand. I look forward to creating some fab outfits now that I have the appropriate shoes. πŸ™‚

    • I am so glad this helped you! 9 times out of 10 my clients have some sort of feet issues so I more than understand! I hope those booties work out!

      • R. Ramirez

        Thanks! I hope they do, too.

  • Brian

    Great post but hard to believe a year has passed since it was written. Before I say anymore I want to talk about the last line in the first paragraph of this post. “I’m too old, too busy and too disinterested to suffer for fashion any longer.” It’s all very true except for the first 3 words.
    There, now I can talk about flats. Sadly I can’t wear flats at work because I’m required to wear a uniform and (you might want to plug your ears) steel toed work boots. YUCK! All of my flats wearing is outside of work. I like your outfits to pair with flats and I try to adapt some of these looks with pants or shorts instead of a skirt for myself.

    Great Throwback Thursday post and of course that means tomorrow is Friday!