STYLE FAQ. So, should or shouldn’t you do so?
If it’s winter and you’re wearing boots, tucking your jeans into them could be a great idea for keeping your pants dry. During other seasons, however, the answer will vary depending on the types of jeans and shoes. If they are bell-bottom or flare, don’t tuck them in. You might as well save your fine kicks for another day since your pants will cover much of the design anyway. Slim-cut or skinny jeans could either be tucked in or rolled up a little right at the top of your high-top sneakers, especially if the shoes have quite a cool tongue to show off. But never tuck your jeans into ankle-high sneakers; you’re only making a fool out of yourself.