What to Wear with Boots and Shooties


There seems to be a range of names given to these kind of shoe/boots, but no matter what you call them, what do you wear them with?

For example, these shooties end at the ankle (all pics from DUO boots which are available in foot sizes 2-10 and in 21 calf size options (30-50cm), and have what is known as a ‘high vamp’ which means they cover the front part of the foot. What the effect of the vamp does is either make the leg appear longer or shorter, which is an important feature, and so tells us what sort of clothes they should be teamed with. So even though you may see these shoes on models and celebrities who are wearing skirts or dresses, what you might fail to notice is that they wearing very short skirts or dresses (which many of us over the age of 25 tend to avoid), so unless we’re 6 foot tall, and have legs that go on forever, then my advice would be to only wear them with trousers, never with skirts or cropped pants, as they make the leg appear even shorter.

If you want to wear boots, wear knee high (not mid-calf) boots with a skirt, they will slim your ankle and calf, and make your legs appear much longer as the leg appears to start at the toe, rather than the ankle, so we get a few inches of extra gam. I love boots, they’re a fantastic addition to any shoe wardrobe, and can be worn both with skirts of any length, with cropped pants as well as under trousers (plus they keep your legs warmer on cold days).

The only woman who can get away with the mid-calf boot is one who has super slim calves, and needs to create some curves on them. Otherwise, keep these under longer skirts or trousers, so we can’t see where they finish.

If you really want to wear an ankle length boot with a skirt, make sure it is one that is open further down the foot, a little like this one, to lower the vamp and show off more foot. It’s best worn with opaque tights in the same colour as the boot, to create a more slimming and lengthening vertical line. I would only advise this if your legs are already on the longer side.


I'm not sure if it's for you but how would you feel if you learned all about the colours and styles of clothing that suit your individual personality, shape and style? Just imagine what it would be like when you can open your wardrobe and pull together fabulous outfits that make you look and feel amazing every day? If you'd like to stop wasting money on the wrong clothes and accessories plus join an amazing bunch of very special women also on their style journey - then my 7 Steps to Style program is right for you. Find out more here.

More from Imogen Lamport

Is it Time to Update Your Activewear?

  This recent humorous video served as a reminder to me to...
Read More


  • Imogen,

    Thanks so much for some definitive advice on this topic. I’m only 5″ 2′, and was dream-dreaming about wearing my black pencil skirt, black wolford tights and patent shooties. I would wear something on top, too!:) Anyway, it seems the shooties ought to stay firmly in the pants outfit category for me. I might have been tricked by fashion magazines to try out this bad look. Thanks for saving me!

  • Thanks for coming by my blog Trish – glad I could keep you from this common mistake.

    If you’ve watched So You Think You Can Dance and looked at the length of Cat Deely’s legs, well, they’re long enough to wear shooties with a pencil skirt!

  • Imogen, Thanks for the advice. I am5’1″. I have a knee-length boots and they are just under my knees.They fit my calfs well but where the boots go over the calfs, there is gap between edges of boots and my legs. I mean, over the calfs, they are not exactly tight to my legs.
    Is it the problem if I wear the short skirt that would expose the upper part of the boots?

  • Thanks for dropping by my blog.

    Any chance you could get the boots taken in by a bootmaker? They can both stretch boots and make them smaller through the calf and above if necessary.

    How much of a gap is there? if they look like wellington (rain) boots, this will look sloppy if you can see the gap. And as you’re smaller, well fitting clothes make you look better, and things that are too large will make you look even more tiny.

  • Thanks Imogen,
    I just tried the boots last night again. From sides, they look great and fit, I only could see the gap when I face against mirror. The gaps are on the outter sides.
    They actually look fine, but I was thinking you are not supposed to have gap there.

  • your opinion please- going out NY eve wearing sparkly top, short black skirt and black shooties- black tights or bare legs?

Leave a Reply

Your email address will not be published. Required fields are marked *