Tucking jeans into boots stylishly this season has been challenging and is the topic of many questions on “Ask Angie“. How can we prevent “bunching”, “overstuffing” and discomfort, and get the look right?

The answer: a specific pair of jeans/pants and the correct pair of boots.

  • Jeans/pants – need to be extra skinny, tapered and hemmed to your ankle. The trick is to have as little fabric as possible to tuck. If you have to fold any fabric over in order to tuck – think again.
  • Boots – need to be wide enough at the calf and ankle so that your jeans lie fairly flat inside them. They can be slouchy, western, sophisticated, equestrian, knee high or calf high in style – as long as there is enough room for comfort when you tuck. 

You might find that you’ll have a pair of jeans/pants and boots devoted to this look alone. It’s always better to buy items that work across a range of looks, but sometimes it doesn’t work out that way. If you love this look – make sure that you match the correct jeans with the correct pair of boots.


The extra skinny ankle length jeans (Nordstrom) on the right are perfect for tucking into these comfortable riding style boots (J. Crew)