Boxer shorts are loose-fitting shorts worn under your clothes as underwear. Making the switch from form fitting underwear to boxer shorts is sometimes challenging. Make the switch less stressful by taking the change in stages. Switching from briefs to boxers for short periods of time allows you to adapt to the fit and feel of the boxers gradually.
Choose boxer shorts in the same materials as the underwear you're currently wearing. Changing the style while staying in the same fabric makes the switch easier to adapt to for many men.
Begin wearing your new boxer shorts over your current undergarments as if they're a pair of shorts. You'll be less uncomfortable while you get used to the fit of boxer shorts.
Wear your boxer shorts as undergarments for a couple of hours a day to help you adjust to the switch from your current undergarments.
Sleep in your boxer shorts. Your skin adjusts to the feel and the movement of the boxer shorts while you're asleep.
Wear boxer shorts as undergarments on a day when you're schedule is full. Your mind will be occupied and you'll have less free time to think about the boxer shorts.