In 4th Edition the magic item clearly stated that you dont take damage and that you land on your feet while wearing them, but in 5e there is no such language in the description. The description of Winged Boots reads:
While you wear these boots, you have a flying speed equal to your walking speed. You can use the boots to fly for up to 4 hours, all at once or in several shorter flights, each using a minimum of 1 minute from the duration. If you are flying when the duration expires, you descend at a rate of 30ft per round until you land. the boots regain 2 hours of flying capability for every 12 hours they aren’t in use. (DMG p.214)
The question here is would they take falling damage from the height they start their fall from, would they only take the last 30 feet in falling damage, or would they take no falling damage?