Reader Request: Flats with Fancy Dresses

flats with dresses

Heather requested some suggestions for how to wear flats with fancy dresses. Fancy is a spectrum, but I’m going to assume that we’re talking about a step above work wear, here: Something that would be appropriate at an office party, night out with the girls, or even something truly swanky like a gala or ball.

There’s no denying that heels give off a dressier impression than flats simply by being, well, heels. But if you’re going to be on your feet all night, dancing, or walking from one event to the next, a towering pair of stilettos is just gonna make you miserable and cranky. So here are a few ways to make flats work.

Select eye-catching flats

fancy flats 1

Fancy flats are gonna work better with fancy duds. Plain, solid ballet flats can certainly blend into a dressier look, but printed or embellished styles will definitely up the ante. Tie the flats back into your outfit by echoing elements elsewhere, using color, accessories, jewelry, or all of the above.

Go long

fancy flats 2
On the opposite end of the spectrum, you can downplay the fact that you’re wearing flats at all by wearing a floor-sweeping maxi skirt. Especially if you select flats in the same shade as your skirt or dress – black is an obvious but elegant choice – your entire bottom half will seem unified. Not the best plan if you’re doing a lot of lively dancing or clomping around outside in the winter weather, but a great bet for more subdued gatherings.

Draw the eye upward

fancy flats 3

If you keep the focus up top through color, pattern, and accessories, your footwear will generally fade into the background. Again, black works well here, especially if you do black tights and black flats. A patent or embossed snakeskin finish will add a bit of polish without drawing tons of attention.

Top image courtesy Zappos.

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31 Responses to “Reader Request: Flats with Fancy Dresses”

  1. Eleanorjane

    Great outfits! I like all of them, but especially the first and last ones.

    I think wearing flats is quite context dependant – where I live in the UK, flats are pretty much standard ‘cos everyone walks all the time. In New Zealand, I was in heels (pumps) daily ‘cos we drove everywhere.

    I’ve got a Christmas do needing lots of walking tomorrow, and it’ll be freezy cold out, so I’m thinking knee high boots (with a less formal outfit than above).

  2. Val

    I love this post…I love all your posts though:). However, because I have MS, it is very important for me to wear flats that seem comfortable so I don’t lose my balance. I never realized until I could no longer wear heels how much the contributed to how “sexy” or “dressy” I felt when I wore them. There are days I long for heels because somehow flats just don’t make me feel as “put together” for lack of a better word. I work in a job where dressing up is necessary, and finding flats that work is a challenge. Also, I don’t have complete feeling in my feet, if they rub, I often don’t know it until my feet hurt so bad they have a bruise or a raw spot. Thanks again for the post on flats…for some of us they are a necessity.

  3. Aziraphale

    If comfort was paramount, I think I would split the difference and wear a pair of elegant but low heels. Ballet flats scram “casual” to me, and spoil the line of a dressy outfit. I’m sure there are exceptions, but off the top of my head, I can’t think of one. (Of the examples above, the only one that might sort of work is the first one, because the dress is quite short, but even so it would work ten times better with a nice pair of kitten heels). Sorry to be a spanner.

    The other option would be to wear heels, and stuff a pair of “emergency” ballets into your handbag!

    • Litenarata

      I’ve never understand the idea that flats “spoil” a dressy outfit. They only do that because our society has decreed that to be the case, so when we dare wear flats to a fancy event people feel entitled to judge. Wearing flats is no more “screaming casual” than going barefoot after two hours when people can’t stomach their stilettos anymore.

  4. Elizabeth

    I hate heels. Aside from the discomfort, I am entirely too clumsy to walk in them. As such, if I am going out on the town or something I usually wear tall flat boots with a short skirt. Although I may not be in heels, there is more sex appeal there than in flats. .

  5. Mickey Lynn

    I wear boots with almost everything! I recently decided to branch out & bought two pairs of ballet flats. Both pair rub awful blisters on the back of my heal. Any clue what I am doing wrong? Guess it’s back to boots for moi.

    • Thursday

      I find it much, much easier to find comfortable low heels than absolute flats – the latter will often feel comfortable in the store and then rub, pinch or otherwise cause immense discomfort after a bit of wear. So you’re not alone!

      For me, I think the key to polished flats is structure – soft, round ballet flats often look flimsy and cheap (not to mention unsupportive). You can still have a solid, moulded sole that doesn’t look like orthotic wear, but adds that bit of sophistication.

    • Sylvia

      Hi Mickey,
      my suggestion is to look at the height of where the top of the flat is fitting on your foot. I have an ankle bone the sticks out a bit on the back & i always check to make sure the shoe is below the bone. sometimes I’ve found it useful to use shoe inserts to lift my foot a little higher out of the shoe & then it doesn’t rub. if the inside of the shoe is rough they sell little heel pad inserts too.

  6. Carol S

    I wish I could replace my pointy toe black patent leather flats. Because they have a dainty toe they look much more like a dressier shoe. Many flats look causal because of the chunkiness of the toe box.

  7. Liz B

    Great post! I am taller than my husband and have going out with the girls shoes and going out with husband shoes. I find it really hard to find flats that look dressed up. I often wear long as you have suggested. Love your blog.

  8. Ruth Slavid

    I do have some heels ( although fairly modest) that I wear for parties. One grey one brown pair, both more than six years old. They always travel with me in a bag as i certainly can’t walk distances in them, or stand up all night. As for ballet flats – unwearable I think. But I have some nice flat black patent brogues (thrifted), also red brogues, magenta patent sandals, orange flat shoes – I think you can pull off dressing up with any of these.And don’t forget how often you will be sitting at a table, with your feet hidden!

  9. Viktoria

    I can´t even do lower heesl anymore without loosing the feel of my toes. For me, it´s all about the way the shoe looks, and for fancier dress I wear patent leather, silk, sequins or something like that. I have noticed that a slightly fuller skirt and emphasis on waist, like the silhouette in the first picture, looks better on me than a pencilskirt, which I would wear more often with heels (when that was still an option). But that is just down to my own taste (and may change over the years). Also, it´s very important to choose one´s pantyhose well. Matt, opaque legwear with shiny shoes just looks clumsy and not very elegant, I find. Better to choose a sheer, neutral pantyhose.

  10. katie

    While I do love the look of heels, I don’t love what they do to the bodies of my patients and to my own knees, hips, and back when I wear them (and I’m 24!) As such, I save my heels for times when the fanciness and flirty-ness is really worth the pain.

    My go-to shoes for dressy occasions are a pair of light gold raw silk ballet flats. The rounder toe-box may not be the most elegant, but it keeps my toes happy. The slubby silk is nicely textured and fancy, and the pale gold color reads as a warm skin tone on my very fair skin. Same idea as the third outfit vignette — with very low contrast, it registers visually as “barefoot” and doesn’t draw attention away from whatever other fabulousness I’m wearing. =)

  11. Cecelia

    Gold ballet flats for the win! I have to stand for church (we don’t have pews) and I could never make it thru with heels.

    Also, anyone know where to find the dress in #3, it is gorgeous!

    • Sal

      Oh, sorry! Should’ve noted: The collages are in Polyvore, so you can click on the images to see item credits. Looks like that dress is sold out, though. Boo.

  12. Christine

    Great post, Sal! At my husband’s office holiday party last weekend, many of the (mostly 20-something) women were wearing towering platform stilettos with their lovely party attire. On the dance floor, they couldn’t do much more than pump up and down and sway. Before long many were barefoot.

    • Anonymous

      It’s a Phase Eight dress and I saw it in one of their UK stores just last week. I was sorely tempted but resisted the urge to buy it.

      • Anonymous

        The above comment was meant to be in reply to Celilia, sorry. The dress is on the Phase Eight UK Website in a UK size 10 (US size 6?) and UK size 16 (US size 12?) only, on sale at £99.00. They will deliver to the UK and to most of Continental Europe, but not to North America.

  13. Julie

    I have these slingback flats (in black) that look good with dresses:'aida'_flat:524081&cm_pla=shoes:women:flats&cm_ven=Froogle,Google_Product_Ads&mr:ad=20584803593&mr:adType=pla&mr:filter=42386772593&mr:keyword=&mr:match=&mr:referralID=NA&mr:trackingCode=D9A1D694-749C-E111-8F17-90E2BA0278A8&origin=pla

    Also, Butter makes several styles of flats that have pointy toes and appear to have a tiny curved heel. They look very ladylike.

    I have bad feet and rarely wear heels higher than 1.5″. It takes some searching to find dressy shoes with very low/flat heels, but they are out there. I have some black satin flats with squared-off pointed toes, and they look great with cocktail dresses.

  14. Olivia

    Not that I was ever able to wear tall heels for a long time without discomfort, but now the arthritis in one of my feet keeps me from wearing even a 1″ heel. I wear flats with a little embellishment on them or in patent leather with whatever dress I like.

  15. Aging fashionista

    I like the fashion groupings you show but I would like to see other kinds of flats, like smoking slippers or menswear brogues (maybe with leggings or tixedo pants or minis) with dressier outfits.

  16. Sisty

    Flats made out of fabric, as opposed to leather, look dressier. Also, flats with a slightly raised heel are dressier, too, even if the heel is only one inch.

  17. Jackie

    If you’re into vintage, take a look at fashions from the mid to late sixties, when very low shoes with broad heels and square toes were exactly the thing to wear with mini-dresses. Some great blocky shoes with a sleek shift that hits above the knee would be retro without being “costumey” (personally, I’m for costume, but I know not everyone is).

  18. lemon drop

    For me the only way to go with flats is pointed toe – I find them so much more elegant and flattering on me than a more round toe.

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