How To Choose Shoes for Skirts or Dresses


How to choose shoes for skirts and dressesShoes are a really important part of your outfit – even though you want to dress your portrait first, we notice the whole of you as you enter or leave a room and if the shoes don’t work, they can create an unwanted focal point, or create disharmony.

So how do you choose shoes? What should you consider?

I’ve made this short video to help you choose shoes to go with skirts or dresses, pants/trousers have different rules (which I will share with you soon).

The key points?

  • Get yourself a full length mirror if you don’t have one!
  • Try on different shoes and see which works best.
  • You can always wear a shoe that is the same colour as your hair – it creates harmony and balance.
  • You can always wear a ‘nude’ shoe that is similar to your skin tone.
  • Think about balance – thicker fabrics need more substantial shoes, very fine or flimsy fabrics need lighter, strappier, more delicate shoes.
  • Then there is the scale of your legs and ankles – fuller legs need thicker soles and straps, finer calves and ankles need finer straps and soles.

Do you have any methods to help you choose the shoes that go with your outfit?


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  • I’ve always stuck to dark shoes myself (yes, I’m brunette) or red — I have a weakness for red shoes. But i have a different shoe question. Because of back and foot issues, it is physically impossible for me to wear heels (or wedges with equivalent elevation). And, in the warmer half of the year, I live in skirts and dresses. I hate wearing pants in hot weather. Because I’m not in a situation wear I need business wear (I’m a p/t lay pastor) I can get away with ballet flats and sandals for everyday (even preaching I dress up, but i wear practical shoes). But there are the odd situations where I feel completely caught out — Christmas parties, or in a few months time, we have a nephew’s wedding coming up. What does one wear on one’s feet on such occasions when heels aren’t an option (I should add that I’m 5′ 7″ with proportionally long legs, so the whole leg lengthening issue doesn’t worry me) Are there any guidelines?

  • I like this post! Espesially I like that you don’t give absolute rules, but explain how different shoes will work, and then everyone can make a choice based on personal preferences, i.e. is ot more important to elongate the leg line (for me personally it is not) or to have a cohesive look and book-end your hair? Personally, I prefer the dark low-vamped shoes on you.

  • What a great post! I love the idea of balance in shoes – it is very important! In the winter boots are a pretty safe bet for me when I’m wearing a skirt or dress – with tights, they go with almost everything!

  • I have similar foot issues as Lynn. I can’t go much over an inch in a heel. I’m quite tall and I always feel that ballet slippers make me look like I’m trying to hide my height. As well, my feet although a normal size for my height look enormous in size 10 ballet flats.

    Imogen, a few months ago when I first found your blog (which I loved immediately) you mentioned a lady I had never heard of before. Carla Mason Mathis. Well, I googled right on over to that site and bought her book. I recommend it to you all. In addition she has 1 hour style webinars. For $29.95 you get to send in a picture of yourself and she will use your picture and the pictures of others to demonstrate certain principles. Or you can check out a pre-recorded on for $9.95. I’ve been sending in my pictures and finding out why some things works and why others don’t. No, I’m not on her payroll and Imogen I hope you’re o.k with me mentioning Carla Mason Mathis again on your site. The Mathis site is Ladies if you love Imogen’s site I think you will also love these webinars. Pat.

  • Loved this post! These detailed explanations with visual examples is one of the reason I love your blog (that, and your great taste!). I haven’t found anyone else that does this.

  • I agree with Lexi! This post was great. Seeing a visual of the different shoes on you really helps to see how hi vamp, low vamp, and nude or dark shoes can totally affect your look. Thanks Imogen – love, love, love your blog!

  • Imogen, the way you combine fashion and common sense while always acknowledging the individuality is brilliant. You did a great job to pack all that info into the short feature film.

    Pivotal fashion moments. I can no longer wear short skirts; I can no longer wear high heels. Maybe we can invent some stylish item that can only be worn when you are a senior lady. There should be something you can add; instead of always taking away. But wait. I am getting off topic.

    Your blog and these features are a wonderful treat for those of us who live a continent away. I always leave your web site thinking, I wish I lived in Australia so I could go see Imogen for a consultation.

    • Wow Anita – thanks so much for your lovely words. I’m really touched!

      There are plenty of stylish shoes without heels – watch out for tomorrow’s post!

      I think statement jewellery is fab on an older person. Wear it with personality!

  • I LOVE this video!!!!! I think it’s really funny (in a good way) how you keep popping down so we see your lovely face. Love it!!!! I absolutely love the dress you’re wearing too!!!! Your style is fabulous.

    • Thanks Sophie! I think it’s kind of weird having a video where you just see my legs the whole time and I didn’t want to be too far away from the camera!

  • I’m short and am wearing a very lightweight summer fabric long skirt to a military retirement party. I know the fabric really calls for a lighter summer shoe but……the military is saying women need to wear closed toe shoes. So, I’m having a difficult time trying to find the shoe that will look right. Seems they all look to be to “clunky “ for the skirt fabric. Please, any suggestions would be appreciated as the party is in July.

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