Heels or flats – what looks best?

by Sylvia

Flats or pumps - What looks better with this outfit? | 40plusstyle.com

Do you go into a debate with yourself on wether to wear flats or heels?

I do this on a regular basis. Do I go for comfort or a nicer leg line? Am I willing to sacrifice some comfort for a slightly fancier look? Do I really sacrifice style when I’m wearing flats?

Let’s put it to the test shall we and compare this outfit with both flats and heels!


optflatsversuspumps (7 of 7)

In favour: Heels elongate my legs and create a nicer proportional silhouette.  As I’m wearing my top over my skirt a longer leg line will come closer to the 1/3-2/3 silhouette that I’m aiming to create.

Against: Heels make this outfit a bit older and more lady-like. And of course they are a lot less comfortable then my flats!

optflatsversuspumps (5 of 7)


optflatsversuspumps (1 of 7)

In favour: if you choose the right flats they can create a funkier look. These patterned flats add a bit of fashion and funkiness to the outfit. Of course they are more comfortable too and make you look like you are not trying too hard. It’s generally a more casual and relaxed look.

Against: I do like the additional length with this outfit and proportionally, heels would be nicer here.

optflatsversuspumps (3 of 7)

Here is a comparison side by side.


So what do you say? Heels or flats?


1 Ashley

Well, I like them both! I do the same thing almost every day when I dress. Sometimes I opt for the heels, sometimes the flats.

2 Nicole

The flats are cuter and would be more comfortable, but the difference in the side by side photos is amazing. The heels make you look taller, slimmer and younger, even though the flats are more “youthful.”

3 Pam (Grey is the New Black)

I think I like the heels better, but my feet can’t handle heels anymore, so I hate to see how much they elongate the legs. I’m sure a lot of my outfits would look better with heels.

4 Pixie @ Cheerfully Vegan

I like them both, but for different venues. The heels dress it up, the flats make the outfit younger and sportier.

5 Sarah

How about more obviously youthful/fashion-forward flats?


6 Ann

I like them both. It depends on what you are doing for the day or event. Great skirt, top and very cool necklace.

blue hue wonderland

7 Sheryl

Really great outfit! Both choices are great but I think I would go with your excellent choice of flats. I would love to see what youthful stle of flats you would suggest.

8 Sylvia

D’orsays are very hip at the moment. They’re on the wish list….

9 Lorraine

I always think an outfit looks better with heels (on me) but I have osteoarthritis in my right toe joint and walking is painful in a lot of flats as well as heels. However, I am seeing a consultant next week to discuss options. Hopefully I can manage to walk around Stockholm this weekend!
I think either looks good on you.

10 Sylvia

Oh have fun in Stockholm. Hopefully you can come up with a solution.

11 Patti

Well, no wrong choice! It’s a great look either way, and I prefer the flats. They give your look a more youthful vibe. xo

12 Becky

Love the flats. I never wear more than a wedge heel myself. It’s not worth the discomfort.

13 Annette

You can wear it with both shoes but I prefer heels. With this look the classy black ones are a bit formal and patterned ones will be great. Ideally a combination of the two 😉

Annette | Lady of Style

14 Greetje Kamminga

I like both actually and agree with your analysis. Which is odd as I hate flats. However, on you they look quite good, especially with this outfit. You probably have a higher instep. I have flat feet and that shows in flat shoes.
However, one piece of criticism…. haha…. as you are comparing apples with pears as we Dutch say.
Yes, the heels make you look more ladylike, but you could also have chosen a funky, modern high heeled shoe. And if your ballerinas would have been more classic (with a little bow… like mine… Oops), the flats would look more classic.

15 Greetje Kamminga

I like the outfit though. Looks very modern and flattering.

16 Sylvia

All true Greetje….

17 Suzanne

I most certainly love the long lean lines that the heels make. The flats, although cute and practical aren’t as kind.

I have this debate myself all the time. I own far too many car/restaurant heels. (Which means I literally can walk from the car to the restaurant and back and that is it.) But oh how I love how they elongate my legs and make me look less stubby. I swear I gain 10 lbs when I wear flats. Shoes are the most difficult thing for me to buy, next to a swimsuit : )


18 Greetje Kamminga

I do so agree Suzanne.

19 Sylvia

I don’t really want to have shoes that I can’t walk in. I’m going to look more for semi-high heels that are good to walk in as well….

20 Rita A.

I would definitely go with those cute flats with that outfit. If you do want to do a heel, I would choose a sling back or d’orsay style. The black pumps seem a little formal.

21 Sylvia

Yes, I agree. Some nice slingbacks would be great… They are on the wish list!

22 Rita A.

Oh, and I don’t know why people think heels are more youthful. I think those cute little checkered flats are very youthful. Take a walk on any college campus and you’ll see adorable flats.

23 Shelley Zurek

Not those heels but yes to heels. Your flats are darling add well!

24 betti

I agree with one of the other posters, the heels make you look younger and slimmer. They are also dressier. It is sort of funny because the flats are sort of funky youthful looking patterned flats, yet they don’t make you look younger. This was interesting to see pictures of outfit side by side with just a shoe change and see what a difference it made.

25 Sylvia

Glad you like this Betti. I should do it more often: same outfit 2 different ways with just a small change ….

26 denton

I think they both look great. In NYC where we live a lot depends on the itinerary, specifically, how much walking is involved. It seems zillions of women wear flats while packing heels for the destination.

27 Trinity

Niether! But I have to tell you that I LOVE, LOVE, LOVE this whole outfit! It is so edgy, but looks totally age appropriate and did I mention that I love it?!

I would do something in between and here is why:
The heels are basic and nice, but dated. They’d look fab with something more conservative, like a suit. The flats are round-toed, which I have never felt are sleek enough.

So what WOULD work? Well….I think a shoe that exposes more of the foot would work–a chunky, low-heeled, black OR white sandal, for example. Maybe patent leather. Or, a higher heel in a bright color that wows. Examples:




Or, if you went with a flat, then try one that is sleek and pointy toed. For example:


28 Mary

I love heels and prefer them with just about every outfit. I wear flats only when I will be doing plenty of walking or am just hanging out. I also prefer sandles over pumps. Fortunately I live in a warm climate.

29 Sheryl

Love-love the snake embossed pointy-toe flats suggested above! They could be a perfit look with this great outfit! 🙂

30 Elizabeth Anderson

The both of them looks lovely

31 maricia

The heels! They make the outfit and legs look better.

32 Lisa

I think the heels look better, but if it’s going to be a heavy walking day be comfortable.

I often wear heels but bring along flats to the office and switch if my quiet day at the office suddenly becomes a running around day.

Of course in real life the problem is flat, low heel, mid heel, high heel, each in multiple variations. It would be so simple if it were a choice between two. And I imagine a heel in a funkier form wouldn’t make the outfit look as formal as the simple black pumps do.

33 Yvonne moiler

I really like the flats – I would like to see an edgier more casual heel

34 Anja van der Vorst

I never have to think or debate about this: heels always look better, more feminine, more sexy, etc etc.

Having said that, that does not mean that flats, sneakers and such cannot look nice as well. They can and they do, especially under trousers.

And they are SO much more comfy and less painful, so I often choose for flats or sneakers.

But ONLY talking about prettier my answer will always be heels.

In this post, both looks are nice, just that the heels look more elegant and feminine.

35 Cheryl

Love the outfit!! Shoes? Well I prefer the flats with this outfit I think mostly because the heels are so black (too much contrast with your coloring), but that is only if you have to shop your closet. I agree with some of the comments about the heels you wore. They are too conservative for the outfit. There are great funky heeled sandals that would complete this look well and I would choose something that is not such a contrast. On an aside. I noticed in the 2 side-by-side pictures that your posture is actually better with the heels (e.g. head is more erect whereas with the flats your neck is more forward). That could have a lot to do with some of those who commented that the heels made you look taller and slimmer. Keep those outfits coming. I can’t always see what looks wrong in my outfits but sometimes I can see it for others.

36 Sylvia

Thanks Cheryl. Yes I agree both in terms of the shoes as well as posture. I will do more of these kind of posts when I return from holidays!

37 Sophie Davis

Hi Sylvia!

I have a passion for heels, so for me it would have to be heels. However, you don’t have my short height and chunky legs problem, so you look great in both. If I’m being honest (and I always try to be), I don’t think the two pairs are directly comparable and the black ones look heavy with the outfit compared to the lighter coloured, flatter pair. I think that a more neutral heel would look better than the black as I think the focus should be more on the fabulous yellow skirt, not the plain black shoe. Therefore, if I was voting for which one you look better in, purely on the balance of colour I would vote for flats.

Either way, you have style, so wear whatever you prefer! 🙂

38 PinkQueen

Love!!!With simple and stylish white yellow

39 Linda in London

I think the heels are fab and really finish off the outfit. I’m a ‘flats’ person but generally only with trousers/jeans.

40 Lisbet

I think you look great in both. I think you have enough black accessories that the black shoes are not a problem. If I were going to the store to get the absolute best choice of shoes for the outfit, I would have to say a black patent sandal or otherwise open toe or heel. Patent is so fresh for summer, and perfectly great in black. I actually have a pair of mid-heel slide in sandals in black patent “croc” that are super-comfy that I would probably slip into if I were in your “shoes” (pun intended).
I have a different question in that respect – for you and others who may want to give me advice. I LOVE heels for what they do for my legs, but like you, I have long, shapely legs and can luckily wear flats without feeling too frumpy. BUT my question is, my husband is the same height as me WITHOUT shoes, so the moment I wear any heal, I feel enormous. I am a larger (overweight) apple, so I don’t know what I should do: Wear heels and look a bit leaner, or wear flat and not “stick” up next to my husband. If I were slender, I think I would just wear the heels but I am so self-conscious in general, I don’t know which way to go. Please let me know what you think.

41 Sylvia

That is a tough question Lisbet. I think it’s very personal. I’m also taller than my husband when I wear heels but I don’t mind so much even though I think he would prefer it if I wore lower heels. There are plenty of celebrity examples where the women are taller than the men and I know some men just prefer their women with heels even if that makes them taller than them. I think that in the end you will have to do what makes YOU feel better, so you will have to determine what is more important to you.

42 Petra

With this particular outfit, I think the heels look best – I’m generally a flat shoe person but I somehow think skirts always look better with a little heel 🙂

43 Lynda North

Comparing black to nude is not the same. BLACK looks bad period. I want to know how to make flats seem dressier. Is it part of the proportion of 3rds thing?

44 Sylvia

The rule of thirds is explained in detail in my courses. You may find this article on wearing flats useful https://40plusstyle.com/how-to-wear-flat-shoes-and-not-look-frumpy/

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