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Boots for the Winter

While boots have entered the workplace, there is far more to boots when it comes to casual and evening wear. Taboos are lowered, but some caution is needed.

If you want to play it safe, avoid the thigh-high boots. Wear the below-the-knee boots, mid-calf boots and ankle boots all you want during the winters.

Matching Style:

Match the boot style with that of your clothing. If the boots are chunky, go for a casual garden dress. For slinky stiletto boots, you will need a party-kind of dress.


Leave a couple of inches between the hemline and the top of the boots. This applies both to below-the-knee boots and mid-calf boots. In all kinds of boot lengths, you can – if you’d like to – do away with leggings and stockings when you are out on a fully casual day. But if you are at work, wear a pair of leggings or stockings the same shade as the boots even if it’s a business casual day. On a casual day out, you can be more enterprising, wearing printed leggings. When you do that, make sure your dress is plain in design, otherwise your attire would look too busy.


You can wear your boots with a pair of skinny jeans or tight pants, tucking the jeans or pants into the boots in a neat fit.

Boot Height:

In casual style, boot height can range from the low ankle booties to mid-calf, to below-the-knee to mid-thigh. Traditionally, mid-thigh boots have been associated with the Julia Roberts role as a hooker in Pretty Woman, but rules have changed since then and with leggings or stockings to cover the skin, they are worn by celebrities in flats or stilettos. But unless you are on stage, we suggest that you wear them over pants, jeans, leggings or stockings.


Matching Colour:

When it comes to casual style, you don’t have to stick to the dark formal colours to match your clothing and the boots. The simplest way is to choose the shades of a single colour. For example, you could choose black boots, grey stockings and black or grey dress paired with a black jacket. To bring more colour to your outfit, you could choose shades from two color schemes. Example brown and black. Mix and match them with the different pieces of your attire. You can stick to a single colour with your boots and another for your clothing, or you can layer your clothing and mix and match with the boots. You can match the metallic accents in the boots with other accessories like the buttons, a belt or your purse.



Leggings or stockings are a must when you wear mid-thigh boots, but for the others, go with the outfit and the occasion. For casual days, you can do away with them, but for business occasions, wear a pair. In terms of colour, wear leggings or stockings a shade different from your boots if you can on casual days. Whether you use leggings, stockings or skinny jeans the same shade as the boots depends on the length of your leg. When short people use a shade that is different from that of the boots, it breaks the length and makes them look shorter. So go for the same colour. But if you are leggy, you can choose to have a different shade.

UGG Boots:

We wanted to add a section for Uggs since they are so popular and right for winter. Flat and warm, they are a neat style statement. But they are casual, so don’t wear them to the workplace. They look good with a casual jacket over your top.


Ankle and Mid-Calf Boots:

Wearing these two styles of boots needs a good calf shape. If you have thick calf muscles, keep away from these. Short pants and mid-length skirts don’t go well with them. Short skirts and dresses, long skirts, leggings and skinny jeans are the right way to go. Keep them simple without too many embellishments.

Evening Style:

Ankle boots give you a great stylish look on an evening out. Match them with your evening skirt or dress. Black is safe and goes with more colours, but there’s nothing to stop you from experimenting with boot colours to match your dress.


Whether you choose to wear mid-thigh, below-the-knee, mid-calf or ankle boots, it all depends on your height, leg shape, the occasion and the outfit. Stick to the basic guidelines, experiment till you find the style that is comfortable to you and sport a great winter style.

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