Wear With Short Boots

Ankle boots with Trousers

The ankle boot and trouser compilation is one of the few in which people make no mistakes. It is the easiest outfit to pull off with flare; however, there are a few rules.

  • If you wear skinny jeans you have to do one of two things depending on their length. If they are long, you need to tuck the jeans into the shoes. Otherwise, you will create bulges at the ankles and this does not look good. If the skinny jeans are relatively short, then you should be able to wear them without tucking them in. However, you do NOT want to show any flesh, as this can make you appear stumpy, unless you are very tall, or unless you wear a very high heel, the skinny jeans should skim the top of the boots, a delicate slouch is allowed, anything more and tuck them in.
  • If you wear leggings, then the same rules apply.
  • With baggier trousers, such as those with a kick flare, you should only tuck the jeans into the shoes if they create a slouch and if the shoes are casual. For example, a pair of straight leg jogging bottoms tucked into a pair of UGGs, with a slouch at the top. If you cannot get this slouch, you should never try to tuck the jeans into the shoes, but have them resting on top. However, this defeats the purpose of these boots as no one will see the ankles.

Ankle Boots with Skirts

There are different rules for wearing this type of shoes depending on the length of the skirt.

  • With a long skirt, these boots are perfect – whether you choose to sport a heel, or wear flats. In general, they look better with a flared or floating skirt, rather than a tight skirt. However, when wearing with a long skirt, as with the skinny jeans and leggings, you should show no flesh – a tiny peep perhaps, but try to hide it all.
  • With a short skirt you will find it harder to look good, particularly if you are short, or a little overweight. This is because the high top of the shoes, combined with the shortness of the skirt, will give the impression that your legs are shorter than they are. To avoid this, choose a very high heel, or alternatively, have very long legs!