thanks for this post Angie. I do not feel frumpy in flats with dresses and skirts thank goodness. For my lifestyle, it’s a good thing!

I am still trying to figure out which length is best for me for skirts and dresses. My knees are pretty banged up so I think my perfect length might be right at the knee because it covers up the scars and gives me a nice length.

Thank you for this post!

Hi Angie… I like the flats with skirts. I often wear skirts with flats, but the skirts I use with flats are all on the casual side. I still use heels if I want to make an impression.

My Mom was a teacher and wore knee-high skirts (just above or just below the knees) a lot. This post reminded me of her formula that I also use a lot: lower heel for skirts above the knees and longer heel with skirts below the knees.

I wear flats with skirts and dresses, although I never tried to wear flats for a really dressy occasion. I don’t feel dumpy at all when I wear flats, especially nice sandals or ballet flats. In fact, when I wear them I feel like what I am wearing is more youthful and fun, than the grown up look with heels. I do prefer to wear pants with heels because they help me elongate my figure.

It does seem that longer skirts need higher heels. Love the look of the first picture. I think the metallic flat dresses up the shoe for the dressier look.

I like “flats” with skirts, especially in the summer. I put flats in quotes because prefer a little heel – .5 to 1 inch on my “flats”. It is just more comfortable and I feel the flat flats don’t have as much cushion under my feet. I feel like I am walking barefooted. I used to do that all the time growing up and I still do around the house, but I find that I need a bit of cushion for all day wear.

Unfortunately, on me, flats and skirts = Italian peasant but not in a chic Dolce and Gabanna kind of way so I usually wear some kind of a heel. I’m also short so any time I can get a little “leg lengthening” in I try to! That may be part of the reason I don’t wear skirts very often.

I think I may have complained about this once or twice on the forum. :-p My feet can no longer take high heels every day, but I have been hesitant to wear flats with a dress. I did feel frumpy and old. But I realized that part of the problem was the length of my hem. With shorter dresses, I have been wearing flats or low-heeled wedges, and I really love the look. More than that, my feet love the look! And I still feel quite fab. Today, I’m sporting a knit, feminine (yet funky) dress that hits about 2 inches above my knees with my Clark Brulees. It is a look that works for work in the city and comfortable to commute on foot.

I would definitely encourage more ladies to try this look.

I rarely wear heels (only for dressy occasions), so when I wear a casual skirt or dress I almost always pair it with flats. I think it’s a youtful and fun look, and for those of us who aren’t comfortable in heels it’s the only option! Other than learning to walk comfortably in heels, I suppose, but I don’t gte much opportunity to practice that!

to be honest, it’s mostly all I wear! I only put on heels if going out somewhere. But during the day with all that has to get done it’s nice to still feel cool and girly wearing skirts and dresses with flats!

I absolutely wear flats with skirts and dresses! I think I’m one of those people that just never fully got the hang of heels, so a good pair of flat sandals or ballerinas are my best friends. And I definitely agree, it’s a surefire way to keep a dressy dress or skirt combo from looking too formal – and gives TONS more mileage to your wardrobe!

Super cute!

I often wear flats, especially sandals, with skirts and dresses in the summer for a more casual look. Being a shortie (5′), I usually stick with some kind of heel for dressier looks. Honestly, I think I would feel a little dumpy if I didn’t. I think stature and body shape has alot to do with it. Angie, as a tall(er) thin rectangle, you probably couldn’t look dumpy if you tried!

I never even heard of this “rule.” My legs are not going to look long or thin no matter what kind of shoes I wear. It’s pointless to pretend otherwise. I wear skirts almost exclusively, even for casual wear, so if I never wore flats with them I’d be a sad, painful-footed girl. If anything, like Danja, I feel odder wearing trousers with flats!

Love, love the second dress. I don’t think it’s too long, as I Do Not Show My Knees.

Wow. I’m pleased that I’m not the only one who wears flats, or a one inch heel most of the time. (Sure, Eva, a one inch heel counts as flat in my book).

Christie, I’m glad you saw the light! Your outfit sounds great.

I wear flats with pants and jeans ALL THE TIME too. I suspect it really helps when the fit is skinny or straight legged, and you’re regular height. Quite flattering and very practical. I like my boot cuts best with a bit of heel, but I also love them with Converse.

I’m with you on dressier looks looking best with heels. Most of the time I wear two to three inch heels for those occasions too. But sometimes I can’t help but slot in a comfy dressy flat instead.

Thank you! I get tired of the fashion gurus who keep telling us the only way to look stylish is to be uncomfortable! I’ve just begun to switch over to skirts instead of shorts for summer, and flat comfy shoes are a must. I think being careful about the hem length and the style of shoes will keep the look up-to-date.

I’ve never been a high heels kind of girl. I think it was my tomboy lifestyle growing up – my Dad was a football coach, so I was more sporty. Then over the years I’ve accquired knee and back injuries which have led the doctors to banning me from “high heels”. I am suppose to keep the heel length under 1.5 inches. I said all that to say this … I love wearing flats with dresses and skirts. I don’t feel frumpy at all. But it does help that I am 5′7 and have longer legs.

Huge fan of flats and agree they can be worn with skirts and dresses. It’s all about the styles you put together.

The first dress you featured is very chic. Love that style for summer.

I wear shoes with less than an inch of heel almost exclusively, and plan my skirt and dress lengths accordingly. I’m 5″4′ and I find that hems that hit about an inch above the knee are best for my leg length and shoe height.

I love this look. I wish I could find age appropriate dresses for a 54 yr old. Most causual dresses show too much skin for me.

Although I’ve been toying with the idea of finally caving and purchasing some dressier flats, I don’t think I’d wear them with anything except cropped pants. My skirts make me feel womanly, and heels enhance that feeling. Flats counteract it, so it would defeat the purpose for me.

I wear flats with dresses and skirts all the time! I don’t feel dumpy – it’s the perfect way to be feminine, put together, yet still practical.

Of course, I am 5′10, with long, almost too-skinny legs.

I love the comfort of flats and wear them frequently with dresses and skirts though more with skirts than dresses. I have no idea why. The length is always right above or at the knee and while I am short, my legs are proportionately longer (e.g. petite sizes are short for me).

I ALWAYS wear flats with skirts and dresses. I love how I can still be fab but not look like I work too hard to achieve the look.

I’ve too many operations on the knees to wear the high-heels of my youth – flats or almost flats are the only things for me now. I’m glad to see as years go by there are more and more cuties to choose from, as more and more ladies are saying comfort please and comfort can be cute and stylish. I’m also one that finds a cobbler that will do just about anything to shoes. I love dresses and skirts with flats. I’ve been to the opera, theatre, ballet, and have seen fabulous gowns with incredible flats and believe me, those ladies look amazing and probably could wear any kind of shoes. Lovely willowy girls on the street with edgy short skirts and even edgier funky flats. It’s all about proportion and putting it together in a believable way.
Right now I’m wearing a balloony, cargo type skirt in black parachute type fabric, black tiny fishnets, black very soft Kenneth Cole maryjanes, brown tissue long sleeve tshirt with a pleat-y neckline and a felted brown and black funky vest – every time I wear this outfit I get tons of compliments and these shoes are flat and very comfy, but cute and edgy, and make me feel very ballerina or dancer.
Enjoy flats with skirts and dresses, the right ones work perfectly and make you look great!

Those pictures mirror my outfits for work as a teacher in Houston. Pure perfection.

I wish I can wear stacked heels more often, but my boyfriend and I are the same height and that would make me tower over him. *sigh* It sucks being tall sometimes.

I LOVE flats! Ballet flats, gladiators, *gasp* flipflops!! I’m short, but my legs are a good 8″ longer than my torso, so I tend to combine above the knee skirts with flats, since I’m not totally confident in heels just yet (plus my boyfriend is EXTREMELY tall; per one of his strides I have to take 2 or 3, and making him wait for me while walking so slowly in heels is a bother).

It’s funny that the last dress is considered a mini; sure, on the model the hem is well above the knee, but on me it would hit right at it! I tend to have to buy dresses that are scandalously short on average or taller women, and then they’re the perfect length for me. I’m always a little afraid of taking up the hem on skirts ,especially ones with detailing like pleats or folds because I don’t want to throw off the proportion or silhouette. It can be difficult. :/

I love the look of flats with skirts in the summer….for some reason I feel *odd* in flats and never wear them. A 2 inch heel is good for me, and I do have several of those as well as the higher.

I must have some distorted strange image of myself in flats because I have been in heels for so many years.:) I am sure Angie could cure that eventually

I barely ever wear heels, so flats with skirts and dresses are the rule, rather than the exception for me!

I think it’s pretty obvious how I feel about this. I’m lucky that I have longer legs I guess, but I think there is just something sweet and a bit retro about flats and a skirt. Angie, you have me drooling over that white mini dress. I would wear that in a heartbeat.

I pair flats with skirts and dresses all the time. I think it works fine in most circumstances.

I love the third pic- but with my pear shape and 5′4 height=NOT!

I mix it up, depending on the dress and the occasion. Mostly I wear it as a casual or young look. But now that I have such a collection of dresses, I might have to try flats as a dressy look!

Wonderful blog!! An absolute wealth of information.
Thanks so much!

I wear flats with skirts and dresses quite often, but only in casual or smart casual types of outfits. If it’s a more formal occasion I still feel like I need heels. This may be because I don’t own any flats that are dressy enough . However, I have already weeded all the uncomfortable shoes out of my closet, so even when I wear heels I am comfortable.

I was just watching a bit of Regis and Kelly. Susan Sarandon was wearing a knee length floaty print dress and dressy flats. Of course she has awesome legs but a refreshing change for sure.
I like a 1inch heel but glad to see Angie thinks that is a “flat” too!

Flats with dresses ALL THE WAY, baby! I am shortish, with short legs, but I have pretty calves, feet and ankles, so no worries. Better to keep the hemline over the knee, though.

Another vote for flats and frocks/skirts. I wear this look all the time, and see many others who do too. It looks fun, practical, and youthful.

Those are pretty. Yea I think they would look good on me!