I remember (unfortunately!) the 90s when I thought I was so so cool with my baggy jeans. They were beyond baggy - I had a 24" waist and I wore 32" jeans. I literally looked like the road-sweeping machines; the ones with the big brushes that sweep leaves off the sidewalks, because my jeans were literally sweeping the floors. So I had to cuff them up and the bigger the cuff, the cooler I thought I looked.
I was so wrong - my family tried many times to tell me so but when you're 13, it all falls on deaf ears.So the question is back - to cuff or not to cuff? Details explored the right ways to cuff your denim and the ways that should be avoided.
Personally, I do cuff my jeans but only a sliver (like Zac Efron pictured above) - it provides contrast and shows off my footwear; perfect if I am wearing boots, high-tops or chukkas. Subtlety is key and less is always more in this case. One good thing about growing older is learning from past mistakes especially sartorial ones.
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