How to wear your flat shoes

by Sylvia

how to wear shoes

Nothing is more comfortable then wearing open flat shoes for summer. However, many women feel that this will make them look frumpy and less elegant.

Although it is true that shoes with heels are often a bit more elegant and can be flattering for your overall silhouette, flat shoes can be very elegant and hip too.

Please note that if you need even more support, I share a comprehensive list of arch support shoe brands together with lots of tips form women just like you who share what works for them.

However, it’s important that you buy the right kind of shoe. Many flat shoe styles CAN look frumpy and you also want to make sure that you wear shoes that fit the clothes you are wearing and hopefully enhance them.

First of all some general pointers:

  • Make sure you buy your shoes in the right size. Many women go up a size in shoe as they age, so don’t assume that you will keep the same size throughout life.
  • More is not more when it comes to shoes. Invest in quality and stick to good quality leather whenever possible. It’s worth investing in flats as you will usually wear them much more often than your heels.
  • Make sure that you buy shoes you can walk in!
  • When your outfit is very basic and simple, opt for trendier shoes to give the outfit a bit more of a young and hip vibe, when your outfit is very hip already you may want to tone it down with simple and elegant shoes. (As usual it’s all about balance).
  • Although you often will match your shoes with one of the colours of your clothes, you can also do the opposite and add a contrasting colour. Make sure though that the tone of colour has the same kind of saturation as the other colours in your outfit. This is easiest to do with black and white, which can be matched with any bright colour like red, yellow, green or blue.
  • Ankle straps will shorten your legs, so be careful with this look when your legs are short.
  • A good thing to look out for is padding. As you age, you loose quite a bit of the natural padding in your feet, so you may need to compensate for that with your shoes.
  • There are quite a few few tools that help make your shoes more comfortable. They include:
    • Inserts, for example Insolia or Foot Petals.
    • Shoes with inbuilt cushioning like those by Cole Haan heels.
    • Custom-made orthotics, prescribed by a podiatrist.

Types of shoes to consider for this coming season:

Pointy toe flats (a chic alternative to heels)

Pointy toe slipper style shoes will be very popular this coming season and they are a chic alternative to heels. Wear them with any style of trousers, skirts or even dresses.

Arty sandals

how to wear sandals

My go-to shoes in summer. Great with a-line skirts, trousers, capris and summer dresses. This will create a slightly more casual look than the very trendy pointy shoes, but these are more comfortable and will still give you a hip and modern vibe. It’s very important that you don’t go for ‘standard’ model sandals. Look for something that’s slightly different and more arty and modern. That is what can make all the difference between a frumpy and young and hip.

Ballet flats

wearing ballet flats

Ballet flats can also be worn with everything. Less trendy but elegant chic for a casual classical polished look.  Ballet flats are not all created equally in terms of comfort and it pays to select those that have padding.  I profiled lots of great ballerinas before.


These are trickier to wear than ballerinas and can look preppy very quickly. Best not to wear them with clothes that are too preppy, to achieve a young and hip look. New hipper styles with either metallic or prints look a lot hipper though and would be the better option for the coming season, like these Fluevogs.



Oxfords are very comfortable shoes for colder weather and look great with menswear inspired outfits. Buy them in a shiny colour or 2 toned, to make them more hip. The same rule applies as for the sandals: if your outfit is simple or one toned, make sure your oxfords are  hipper. If you have a very hip, multi-coloured outfit, then you can get away with neutral one-toned oxfords.

Fitted knee high boots

Great with trousers and knee high skirts in colder weather. Make sure they are well fitted around your calves though for a nice slim and elongating silhouette. Riding boots are one of my favorite boots and I have featured some of the best earlier.

Comfortable walking shoes

These are the shoes you need when you will spend the whole day walking. Brands to look out for when looking for comfortable shoes include Cole Haan, Arthur Beren, Anne Klein’s iFlex series, Dansko, Born, Ecco and Attilio Giusti Leombruni. Let me know if you have any other brands to recommend. I’m particularly looking for brands that stock shoes that are both comfortable AND modern.

Here is a range of hip flat shoes that you can currently buy online.

What will be your go-to flat shoes this coming season? Also, if you have any further tips when it comes to shoes, let me know!

{ 16 comments… read them below or add one }

1 Rita

Ah…the Attilio Giusti Leombruni’s (AGL’s)! My go-to ballerina flats. They are so comfortable and come in tons of color combinations and textures. I admit I have several pair. For comfortable walking shoes, I also like Paul Green (a German brand), though lately I’ve found their styles to be a little frumpy. Both brands are great, though, for my easily blistered feet! I love the riding boots I bought this fall. Very sharp looking, and will be fun when I mix them with a lighter summer dress and cardigan (it’s been a bit cold to try that).

I think one thing to keep flats, and really all shoes, looking their best is to really take care of them. Get rid of scuffs right away, touch up any scratches or dents in the soles (a black or brown Sharpie marker works great), and keep them polished. For me, nothing ruins an outfit like worn out looking shoes.


2 Sylvia

Yes, I remembered your recommendation so I made sure to include them in the comfortable shoe lineup 🙂
Some great tips for taking care of your shoes Rita!


3 jj

hi Sylvia, i love flats!!! yes, i find them really flattering for us over-40s. btw, i just adore your red tote in one of the pictures above. can you tell me where you bought them? i’ve been looking for something red and functional like them. thanks! – jj


4 Sylvia

The tote was bought while in holiday. Not sure which city, but it was in a local shop, so I don’t think you can get it anywhere else… Good luck in finding something similar.


5 Alice

I love wearing flats but do not wear them to work. I work in a conservative office and to me flats just feel way too casual.



6 Sylvia

I would wear dressy flats to work for sure. Like dressy oxfords, ballerinas or loafers.


7 Nanne

I love the outfit with the shorts, shirt and the funky sandals, it’s really cool! I would like to add an (in my opinion) importan notion when it comes to wearing flat shoes, and that is posture. Where as a heeled shoe can actually improve your posture, you need to pay more attention to this when wearing flats.


8 Sylvia

Very true Nanne. Thanks for pointing that out!


9 Greetje Kamminga

You said: “Make sure though that the tone of colour has the same kind of saturation as the other colours in your outfit”. This is difficult for me. I have a vague notion of what you mean, but I cannot apply it to my outfits. Just have no idea what to look for, how to define the saturation.
Furthermore: I buy flats because I need shoes to walk on for a longer time in summer. Like Rita, my feet blister easily. And if I do a city tour, I definitly need flats and they have to be able to hold my special comfort inlays.
With a low instep it is not easy to find nice flat shoes. (I had to laugh over Nanne’s remark about posture. Last week I was wearing flat boots and somebody mentioned the way I walked. Apparently it was like a horse carrying a load. haha)


10 Sylvia

You would be able to tell by looking at 2 colours from a distance or squint your eyes. If one stands out a lot more than the other it’s usually more saturated. It’s usually nicer to combine colours with the same kind of brightness.
Yes posture. Always so important. As you know I’m constantly working on mine. Doing a lot of Pilates at the moment to improve it and solve my back issues….


11 Playing with Scarves

These flat shoes are perfect on you, Sylvia. You made me feel like wearing some. Bicolor ballet shoes would be my choice #1. OK. Ready to try 😉
Have a great weekend,
Anne Touraine (playing with Scarves)


12 Sylvia

I agree Anne. Those would really go with your chic style. My scarf variations coming up tomorrow. Stay tuned!


13 Wilma

One thing I always consider when buying open toed sandals or flip-flops is how well the shoe suits my TOES. Those of you with cute toes that evenly decrease in length can probably wear any shoe, but many of us have ugly toes, uneven toes or extra long second toes, so the width and placement of the strap across the front of the foot, right before the toes begin, can make a big difference in appearance. I can’t wear flip-flops, sandals with toe straps, or sandals with thin foot straps without drawing attention to my ugly “pedatarsals”!


14 Sylvia

Very good point Wilma. Thanks for the feedback!


15 Petra

Hi Sylvia. I agree totally with Wilma re how your “toes” look in summer shoes – it actually determines whether I buy the sandal or not. Also, when wearing open-toed sandals; very important for your feet to look good e.g. nail polish and moisturiser. I love black ballet flats – Audrey Hepburn-style – looks great with so many styles of clothes.


16 Sylvia

I agree. If you want to wear flats and be sure you look elegant, ballerinas are the way to go!


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