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If you're doing it because of 'fad'... you're doing it for the wrong reason... looks like a few have done it tho... my person opinion, is that 23" would be your upper limit... and again, that's just my opinion... you can, and should, do whatever 'you' want.
There is a member on here (Dyna_bagger85) that had a 23" on his bike.
Here are some pics of it on his ride before he sold it. If you have any questions, send him a PM, he should be able to help.
I run a wide 21" on my ride.
Road pretty good but since have gone back to stock wheels. A steering dampener would of helped out a lot. I know putting preload adjusters in helped quite a bit.
I do think that a 23 would be detrimental to the handling though but people have their bikes for different reasons, and if you like the look, go for it.
I personally dislike the big wheel stretched baggers, they look proportionally wrong. The main iconic part of a Harley is the big V twin motor, a stretched big wheel bagger makes the motor look like a pit bike motor in a huge frame and just ruins the look.
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