How To Style A Denim Midi Skirt In Winter

This week over on my Youtube channel I wanted to share another midi-skirt video, this time focusing on a new shape and fabric. About two months ago I shared how to style a pleated midi-skirt, this week it’s all about the denim midi skirt and the style I’m using is a pencil shape.

We all love denim and for many of us it’s our primary go-to so I wanted to share some ideas and tips around this skirt to hopefully give you some inspiration!

Denim Midi Skirt Outfit Ideas | Winter Denim Skirt LOOKBOOK


These skirts are designed to start at your high waist and end mid-calf. Because they’re denim, they should have a nice firm (but not tight) fit. The best type of denim for a pencil-shaped midi skirt has a little bit of elastic in it to allow you to move about and, that little bit of elastic will hold your shape beautifully. For a full down of fit, you can check out this post.


Think of blue and black denim as a neutral and focus on matching other parts of your outfit. For example, you could match your shoes to the colour in your top, your coat to your jumper, your boots to your bag. Pick up the other items you’re wearing and try to match those. Your skirt is just like jeans, a canvas for other items.

These skirts are designed to start at your high waist, which means your high waist should be seen when you wear these. This often means tucking in your top, belting your waist or if you wear cropped items, a cropped top or sweater. If you cover your high waist in this garment, you’ll end up shortening your figure.


In winter, knee-high or thigh-high boots are great because they end under your skirt, as opposed to before your skirt ends. Pairing stockings with a closed in heel can also look great and keep you warm in the cold months. Come summer, the denim midi skirt is still super useful, you could be wearing a strappy heeled sandal or even a fun pair of wedges.

I tend to avoid flat shoes with pencil-shaped skirts as this can make the wearer look shorter than they are, it’s best to opt for a little heel.

I hope you enjoyed this weeks video! As always, if you have any ideas for future videos please leave comment here or over on my youtube channel!

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