Tucking jeans into shoes can be a fashion statement when done correctly, but not understanding the trend can lead to a disastrous faux pas. To pull off the look fashionably, men must remember that the purpose of the trend is practicality rather than style (think cowboys or military men who don't want to dirty their boots). When tucking your jeans into your shoes, you need the right kind of pants and the right kind of shoes to pull it off properly.
Put on slim or tight pants to avoid a baggy, bunched look, which is sloppy and not fashion forward. Remember that comfort is key. Made Man contributing writer Darrell McBreairty advises, "jeans can be wrapped around the ankle areas and shoved into a pair of cowboy or dress boots, but heavy wool pants or even corduroy pants are not as accommodating."
Pull on mid-length shoes. Madeline Weeks, the fashion director of GQ, advises, "the proportion of the boot and the pants has to be right. You don’t want to the boots to be too short or too tall — say, four to six inches above the ankle, or up to eight if you’re really going to go there.” Shoes that are too short or too tall look gimmicky, not fashionable. The idea is to look outdoorsy, so any sort of classic workingman boot should do the trick.
Wrap your jeans around your ankle and tuck into your shoes haphazardly. Make it look like you just shoved your legs into your shoes and ran out without giving the mirror a thought. According to Ray A. Smith of the "Wall Street Journal," tucking shoes into jeans can look pretentious and show off-y. To avoid this, Smith suggests making the look appear cavalier and accidental. Made Man's McBreairty writes, "You may have to resort to stuffing the pants legs into the top of the boots in such a way that they retain a crumpled sportsman-like look." Tie laces haphazardly to add to this look.
Tuck jeans behind the tongue of high-top shoes. According to Amanda Lawson of Zigoti.com, this not only allows you to show off your shoes, but also "high tops tend to hold your jeans from draping to the flow when you tuck them behind the tongue." While high-top shoes can be worn with either slim-fit or baggy shoes, baggy jeans and high-tops convey a more gangster look (as worn by Jay-Z in the Zigoti article) and skinny jeans convey a more pulled-together look, and tends to look better on fit people.