When buying 501s, expect to go up at least two to three sizes from your regular waist. For a boyfriend fit, go closer to four sizes Also, note that fit can vary slightly by decade. Levi’s has a pretty comprehensive guide, but basically: The older the pair, the more high-waisted and stiff they’ll be.

Do Levis run big or small?

One important note on these jeans: they run VERY small. Like I said above, I typically wear a 26 in most other denim brands, and a 27 in the other Levi’s styles I own but I wear a 28 in these. So I would suggest going up two sizes… which seems crazy, but trust me on this one!

Should I size up in Levis?

For those who want to machine wash and dry the jeans, we recommend sizing up. For your waist, increase 1″ for sizes 27″-36″, 2″ for 38″-48″, and 3″ for 50″ and up. And for your inseam, increase 3″ for sizes 27″-34″ and 4″ for 36″ and up.