Reader Request: Flats with Dresses

How to wear flats with dresses


Reader Kelly e-mailed me this request:

I would love to wear heels and when I was younger and without scoliosis I did; now they seem to be a thing of the past though I keep trying. Could you do a post about flats? Specifically how to make them look good with dresses ( I don’t think they do) or anything for that matter.

So I’ve written a bit about flats and have several posts in the archive with visual examples, and I sent those along to Kelly:

  1. This post talks about making flats work with fancy dresses
  2. This covers balancing shoes and shorts

But let’s talk about flats with dresses. Of the non-fancy variety. And I can hear many of you scoffing through your computer screens as I am a confirmed heels lover myself, but at least give me a shot!

Flats are extremely important. I don’t wear mine as often as I should, but I’m trying to incorporate them more frequently because there is a growing pool of evidence indicating that a steady diet of high heels can cause serious, long-term health issues. Flats also have a bad rep. We are trained to favor a long leg line, and told that flats cause our legs to look stumpy. I, personally, find flats to be tougher to style during cold weather because they can look a little odd paired with tights.* And make walking in the snow an unpleasant experience. So, ya know, uphill battle. But it can be fought.

Assuming that the main concern is leg-elongation – which is usually the case – here are some ways to make flats work with dresses and skirts:

Opt for higher hemlines

We’ve all got our hemline happy zones, and I’m not suggesting you veer outside of yours. But since flats won’t give your legs any lift or length, showing a bit more leg near your dress or skirt hem will help your legs appear longer. Even an inch will help, I’ve found.

Pair with like-colored tights

This is my flats-in-winter solution. Any time you can do hosiery and footwear in like colors, you’ll elongate your leg line. That low contrast allows the eye to travel all the way down the leg nearly to the ground before stopping.

Match your skin tone

And when it’s warm out? Allow me to trot out a piece of style advice that will never, ever die: Shoes that match your skin tone make your legs look longer. This includes flats. Go for something in a nude-to-you color.

Go for low vamps

I’ve seen so many women pair oxfords and dresses to great effect. I have never successfully done it myself. A high vamp shoe will cut your leg line higher up, so if you want your legs to look longer pick a lower vamp style. Ballet flats are a reliable favorite.

Experiment with shapes

I am always, ALWAYS drawn to round-toed everything. But when it comes to leg-lengthening, round toes fail. Pointy-toed flats have been trending for several years now, so consider trying a pair if they’re not too uncomfortable. If true points don’t suit you, go for a middle ground between round and elvish.

Try boots

This may or may not work for Kelly, but it’s something to consider if you prefer flat footwear but your eye just won’t adjust to other flat shoe styles. Boots offer an entirely different level of coverage and break at very different parts of the body. (Info on boot height and leg flattery here.) Depending on your proportions, flat boots may look more appealing than flat shoes. And remember, boots can work in summer!

Match shoe and dress styles

I’m a fan of juxtaposition, to be sure, but aligning styles can feel far more natural. Polka dot ballet flats with a red bow on the toe will look slightly “off” worn with a structured sheath and blazer. Super athletic flats probably won’t work as well with a retro-influenced shirt dress. Make sure you’ve got a few flat options available so your dress and shoes will work with each other.

Direct focus elsewhere

Even if you’ve got low-vamp flats and a slightly high hemline going on, you may still dislike the overall look. But if you’ve gotta do flats, you’ve gotta do flats. So consider diverting attention from your feet and legs. Wear a bright or printed top. Try a statement necklace. Cinch your waist with an eye-catching belt. As always, distraction tactics can be incredibly helpful. If you’re not wholly pleased with the bottom half of your outfit, make sure there’s something fabulous going on up top.

*I’m talking ballet flats, loafers, oxfords, and the like. In my experience, flat boots are a bit easier to pair with tights.

Originally posted 2013-03-18 06:37:20.

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28 Responses to “Reader Request: Flats with Dresses”

  1. Susan

    I LOVE LOVE LOVE flats, and I am always on the look out for great, well constructed flats. I wear them with dresses with tights, matching the shoe and the tights. I find that a low heel, as in a loafer, makes a huge difference in making the leg line look great. While harder to find than ballet flats, low heeled flats and loafers do exist, and are worth hunting down. Zappos helps a lot; searching by heel height narrows the field. Sometimes I take flats to the cobbler and have a sole and heel added for a bit more height and cushioning.

    Classic equestrian boots look great, too.

    To foot, knee, and hip health! Salut!

    • Halo

      I’ll add that a low heel is more comfortable for me than a ballet flat, and I’ve read it’s healthier for your back and legs, too. By low I mean like 1/2 inch, like a loafer as Susan says, or a flat boot.

  2. Marlee

    I wear flats with dresses all the time! I’m in high school so when I want to wear a dress, I wear flats to dress it down a bit. (Also I’m really a klutz and can’t walk in heels very well.)

    If I wear tights, then I match the tights with the shoes. Otherwise it looks weird to me. Once or twice I’ve paired my trusty black patent leather flats with colored tights, but I didn’t like the combo much.

    Overall I’m not a big shoe person, so I usually go for very plain, solid, usually fabric, ballet-style flats. The tendency towards solids probably also has to do with most of my dresses being prints.

  3. Hearthrose

    I don’t have a choice about wearing flats – very supportive flats – and I wear dresses or skirts every single day.

    Flats tend to read young and/or cute. Be very very aware of the lines of your clothing if you want to look professional.

    Boots are awesome.

    I personally tend to wear Mary Jane type shoes, with a strap… but I can’t wear ballerina flats. I get a lot of compliments on my cork patterned version – it doesn’t look anything like little-girl shoes.

    So yeah, be aware that they can read young and cute and take measures appropriately.

  4. Lucy

    I love knee length skater dresses with flats, but I have quite short legs (exactly inbetween petite trouser length and standard) and I’m only 5ft 3 inches so no heel will ever make me look leggy. I just tend to embrace the stumpy and wear a long cardigan with said dress and quite often leopard print or brightly coloured flats. I actually feel a bit silly day to day in dresses with heels as I work in a very casual office and it makes me feel like I’m going to a wedding or something!

  5. Becky

    A great and timely post, thank you! I made a switch recently from pants to dresses for my everyday look, and it’s really working for me. But — I live in a rural area and can find myself walking on rugged terrain (farm fields, woodland trails, unpaved roads) in the course of any normal day; so sturdy shoes that stay on my feet are a must. Boots are a no-brainer in the fall, winter, and early spring, but I’ve been scratching my head a bit about summer footwear since I need a low heel and sandals aren’t always going to work. This post has given me some good ideas.

  6. Anneesha

    This is a timely post! I am waiting to get orthotics – and am afraid of what my footwear choices are going to be from here on out.

    • Hearthrose

      Mary Janes will often cover an orthotic. You’ll want to find a shoe store that specializes in orthotics and comfy shoes. Boots, again, are the *bomb* with an orthotic, and can give your whole foot extra support. I speak of lace-up boots, of course.

  7. Noemie

    I wear flats virtually every day. Or flat boots. Or Converse. Or flat sandals. The point is, my knees don’t allow me to wear heels very often or for very long, so they’re just plain out for day to day wear. And personally, I think flats look great with dresses, particularly ballerina flats. There is a playfulness to them that is nonetheless understated; it makes an outfit with dress or skirt feel fresh instead of formal, IMHO. Nobody has ever mentioned not liking the look, and if they did, who gives a damn? I look and feel great.

  8. anya

    Angie on youlookfab dot com is a mainly flats wearer and she has some great outfits with frocks and flats. I think it’s a great outfit archive if you wanna see some fab implementations

    • Devon

      Zooey Deschanel wears a lot of flats with dresses–definitely on New Girl, but also in real life, too, if my google search is any clue.

      As a runner, I go by the motto that high heels are like dessert: they should be a special treat and not for every day. My feet and the rest of my body is a lot happier for that. In winter, I tend to wear flat boots and in summer, shoes that are similar to ballet flats but with more support. You have to get used to the look, though. I feel like flats with a dress are more cute than sexy, but I’m not going for sexy most of the time anyhow.

  9. Debs

    I wear nothing but flats. I have long waist, short legged and not very tall 5’4″. I wear the same color bottoms as my shoes to create the longest line possible… or I wear taupe. This is the only way. I have arthritis and if I don’t wear proper shoes it feels like I am walking on glass. So I order special shoes on Zappo’s and pay for good quality shoes. Sometimes I wish I could wear those cute ones at Target but nope, no way. I do have a pair of kitty heels that I wear on special occasions. That’s about it.

  10. LK

    Does anyone have a brand of flats they could recommend? What I find with flats is they are, well, flat. No arch, no support and usually very thin soles. Its like walking barefoot on the ground which for someone with a high arch is very uncomfortable. If they have a strap, a support can be added but I find that the additional support forces the foot out of the shoe. I never have any luck with flats!

    • Devon

      I like clarks and I just got a pair of earthies that has quite a bit of arch support. I usually find that a shoe with a very small heel (like 1 inch or less) is slightly more comfortable for me than a straight up flat shoe).

    • Debs

      I wear Archipedico… think that is spelled right. Ecco looks like they have some cute ones, Clarks.. Sketchers…

  11. Rtuth

    I almost always wear flats. And they always have a fastening. So I guess what you would call ‘oxfords’ and I call brogues, with the occasional Mary Jane. My legs are short and could be slimmer. But my ankles are slim so maybe that is why I don’t care. I love coloured tights so none of that matching malarkey. But I really hate ballet flats – they are uncomfortable and to me they look like slippers. To me a bit of sole thickness makes my ankles look more delicate. And when I do wear heels, I actually worry that they make my calves look big.
    The big rule for me with boots is that they must fasten or be elasticated. I had some beautiful cobalt suede boots and I got rid of them because they were too loose and made my legs look like tree trunks. As my calves rose out of them it looked as if my legs were that width all the way down.
    Ankle boots are great, and knee high. My only disaster are some flat black Camper boots that come to just below my calves. Not really a disaster as they are about 10 years old and I wear them lots. But only with trousers. With skirts they make me look like an All-In Wrestler.

  12. katie

    Thank you, thank you, thank you for acknowledging that positive-heeled shoes are actively detrimental to health! You are the first fashion blogger I’ve seen do so, and as a professional-in-training helping women deal with the consequences of their lifelong shoe choices, it’s not a moment too soon.

    I mean, dang, heels are adorable. But dang, painless knees and good circulation is pretty sweet, as well. =) I’ve recently discovered how much I like open-toed and d’Orsay flats — professionally, I have to wear closed-toe, but personally (and now that it’s getting warm enough, in northern CA) I love what that little peek of toes does to lengthen the visual line. Generally, I prefer “classic” pumps/ballet flats or t-straps rather than mary janes — I’m short-waisted with looong legs and short, wide feet, and having a strap across the vamp visually makes my feet look ever choppier. Somehow, I find that the additional linear strap of the t-strap continues to pull the eye along the foot, and now the open-toe (how did I never know that I liked this before?) does the same thing, which is especially great for flats.

  13. Devon

    re: foot support in flats.

    I buy the 3/4 length insoles at the drugstore. They have to have a firm arch support in them to help me, so I never bother with the cheap, flat, foam insoles. Dr. Scholl’s makes a good pair called “tri-comfort orthotics”. The back of the package shows the firm arch support, and you can also feel it through the hole in the packaging. Larger drug stores sometimes have a store brand. Also, if you’re buying a few, it might be cheaper to go online. Dunno for sure.

    They made my Converse sneakers wearable for a walk-all-day retail job on flat concrete. The 3/4 length means my toes don’t get squished.

  14. CC

    I wear flats pretty much all the time (heels only once a week) and frequently with tights and skirts. My favorite tights look is my burgundy tights and burgundy flats. I have also found flat sandals work pretty well. It is really a matter of finding flattering skirt lengths and flattering shoes. And getting used to the way it looks. 🙂

  15. Gel

    Sally, thank you for this timely post! I just started physical therapy for a sports injury. I showed up to my first appointment with 2″ heels, and even though they were Dansko heels, the therapist scolded me and told me I should wear heels during my recovery, and that heels in general are bad for us. I appreciate your suggestions on how to wear flats and still look stylish.

    To LK who commented above, my favorite flats are by Cole Haan! I have ballet flats, loafers, maryjanes, and oxfords by them that are my staple shoes. They are comfortable, they break in like a dream, and are well-made. They’re pretty hard to swallow at full price, but if you look often enough, they can be found with decent markdowns at, Nordstrom Rack,, Saks Off Fifth, and even TJ Maxx.

    • Gel

      Oops… I typed, “the therapist scolded me and told me I should wear heels” when I meant to type, “the therapist scolded me and told me I SHOULDN’T wear heels.” That was tough news to take, because I really love high heels.

  16. A.B.

    Thanks so much for this post! I wear nothing but heels. Although I admit that I rarely wear dresses.

  17. Lydia

    I enjoy my flats, but I find ballet flats too flat to wear, and the toebox of most ballet flats is too small to fit my orthodic. What I do is I look for a slight wedge, or low heel — 1 inch, and this is even more comfy than a ballet flat. Also, look for ballet flats that have more of a rubberized heel (like Naot). This is more comfortable, although offers a different look. Avoid very thin ballet flats, as they are really uncomfortable.

    I do recommend Clarks Unstructured (approved also by foot doctor), as they offer support (though he said they were too soft and bendy, but I like that!) I have tried many interesting brands (not bought, just tried), and there are some really interesting flats, or slight wedges (my favourite) from other countries that are amazing — too bad they usually sell out of my size!

  18. Viktoria

    I´m a flats only person with very narrow heels, and I have found that Vagabond offer good ballet flats that I don´t step out of. Generally, though, boots are what we wear most in my neck of the woods.

  19. Bree Bronson

    I’m tallish and have small kids so flats are often a matter of convenience. So thank you for this post! I often try to find fancy flats so the focus would be on their fanciness rather than the lack of heels. Works often rather well!

  20. Eleanorjane

    I think the flats with skirts/dresses thing depends on your context. In my city in the UK there seem to be a lot more variety of flats and they are a lot more commonly worn as people tend to walk (or cycle) to work, to the shops, to the pub etc.

    So, I bought about 8 pairs of heels with me and I haven’t worn some of them even once! I’ve bought flat boots for winter and flat shoes for summer. Clarks are good for flats with a tiny heel and reasonably sturdy, comfy construction.

  21. Kelly

    Oh Sally, you are such a sweetie. I miss a couple of days and you’ve gone and done a post on my question. Thanks mucho! Thanks also to all the lovely ladies who weighed in on the flats issue, such great suggestions. I love the idea of boots (but that’s just not possible in Vegas summer); still, it’s not summer yet!