What Footwear to Wear With Cropped Trousers In Winter

Have you got some cropped trousers hanging in your wardrobe that you love but aren’t sure how to wear them without exposing your ankles? It’s a question I get asked a lot and as someone who really feels the cold (I’m currently adding more of Uniqlos Heattech thermals to a basket!) the good news is that you can wear them with the appropriate footwear and styling techniques, all without sacrificing warmth! Here are practical tips and ideas to guide you on wearing cropped trousers during the chilly winter months while staying both warm and stylish:


  1. Sock Boots

These sleek, form-fitting boots not only keep you warm but also add a touch of sophistication to any outfit. Pair them with cropped trousers for a seamless, elongating effect. Opt for neutral tones like black or gray for a timeless appeal, or experiment with bold colours to make a statement.

2. Loafers and Brogues

Loafers have always been a popular transitional shoe with those who favour a preppy aesthetic. Traditionally they feature a classic slim sole or most recently a heavier lug sole. When paired with cropped trousers, they create a polished yet relaxed ensemble. Add contrasting or pattern stocks to make a statement or a plain black sock or tight for a more paired-back style. A cropped trouser that hits just above the ankle works wonders with loafers.

3. Pointed High Shaft Boots

These boots elongate the legs and exude confidence and sophistication. When worn with cropped trousers, they create a modern and edgy look. Consider opting for a monochromatic palette to keep the focus on the sleek lines of the boots. Keep the rest of your outfit understated to let the boots take centre stage.

4. Trainers and Socks

Add an extra layer of warmth and style by wearing cozy socks that peek out above the ankle. For a sporty-chic look, pair your cropped trousers with trendy trainers and cozy socks. This combination adds a youthful and energetic vibe to your outfit. Don't be afraid to play with patterns and textures in your socks for an extra twist. Choose trainers in neutral tones or opt for a pop of color to inject some fun into your winter wardrobe.

5. Booties

Booties are a great option if you don’t mind showing a bit of skin or sock. Opt for ankle-length booties with a slight heel for a flattering silhouette. Consider matching the colour of your booties to the trousers for a seamless transition. Try trousers with a slight flare to cover the top of the booties.

6. High Tops

High top trainers adds a touch of urban flair to your ensemble. Pair them with cropped trousers for a fashion-forward look that's both comfortable and stylish. Opt for a pair in a contrasting color to create visual interest. Experiment with different color combinations to express your unique sense of style.

Top Tips:

  • Ensure your cropped trousers are the right length. They should end just above the ankle or at the slimmest part of your leg.

  • Consider the colour palette. Neutrals and classic colours work well for timeless elegance, while vibrant hues can add a pop of personality.

  • Experiment with sock choices to keep your feet warm and complement your overall look.


I hope this will help you embrace your cropped trousers over the coming months.

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