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How to keep a healthy beard with very picky skin?

So I've had a beard off and on for the last 8 years and I always end up shaving it off when it gets to about 6-8" long because it just starts to dry up on the ends and I'll get split ends that will go all the way to the root. The weird part is my beard hair will very greasy and oil for the first 1-2" and the rest will be dried up. Any shampoo, conditioner, oil, balm, anything I've ever tried has always given me very bad pimples and bumps under my beard. The only product I've had success with is Dr bronners however that eventually leads to minor bumps and even though it helps the oily part of my hair, it furthers the drying of the dry parts of my hair.

So basically I can have bad pimples and bumps plus extra greasy roots to help the tips not dry out and split or I can have less pimples and bumps and help dry out my roots but have worse dry split ends or I can just let it go, not wash it or do anything, let the stink grow, and actually have a manageable beard and just deal with the issues.

Is there some miracle product I'm not aware of? I'm growing my beard out again and am only a few months away from this starting again so I'd like to try to catch it early.

I've always had better results from "less is more" in terms of products. Maybe working some witch hazel into it every few days?

I also started using a boar hair brush which helps work the oils out to the tips but my beard is so thick that by the time I've got 6 months growth it won't get through.

How about pine tar soap? Or the cremo beard softener? Anyone have experience with these?
 
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Do you do any trimming? Getting rid of split ends before they run all the way up may help.

Occasionally but not as much as I should. I've ruined many a beard trying to trim myself and my hair is so curly that even the best of barber trims still results in severely uneven growth. I'll wait until about 4-6 months and get an initial shaping then will get a proper trim every 2-3 months from there
 
Antica Barbiera Colla's line of beard products are amazing. I had troubles with other beard oils and such but this stuff is unbelievable. Pricey, but worth it. I have the beard oil, balm, and shampoo. Great stuff. And while you're at it pick up the Capsicum and Menthol Lotion for your head hair. You won't be disappointed.
 
Trimming at home can be pretty scary, but it's not to difficult once you've done it a few times. You can either use scissors or a clipper without a guard. Just style your beard how you want it, then start out past your beard ant trim of the flyaways but don't get into the bulk of the bead. you may even feel like your not cutting any hairs, but listen and look for anything coming off. Comb or brush through and do it again. Go very slow and do it when you have plenty of time. If things go wrong you can go to the longest guard on your trimmers to even things out without scrapping the whole thing. Hair trimmers actually work better than beard trimmers when dealing with a big beard and have longer guards. Or if you have a good barber locally you can go that route.

Another tip is when applying beard oil start at the tips and work your way to the skin, the longer your beard the more important this becomes. If you cant get your boar brush through it start with a pick or wide toothed comb to get through firs then switch to the brush after you've gotten through the curls. I've never tried Grandpa's pine tar soap, but a lot of guys really seem to like it.
 
Trimming at home can be pretty scary, but it's not to difficult once you've done it a few times. You can either use scissors or a clipper without a guard. Just style your beard how you want it, then start out past your beard ant trim of the flyaways but don't get into the bulk of the bead. you may even feel like your not cutting any hairs, but listen and look for anything coming off. Comb or brush through and do it again. Go very slow and do it when you have plenty of time. If things go wrong you can go to the longest guard on your trimmers to even things out without scrapping the whole thing. Hair trimmers actually work better than beard trimmers when dealing with a big beard and have longer guards. Or if you have a good barber locally you can go that route.

Another tip is when applying beard oil start at the tips and work your way to the skin, the longer your beard the more important this becomes. If you cant get your boar brush through it start with a pick or wide toothed comb to get through firs then switch to the brush after you've gotten through the curls. I've never tried Grandpa's pine tar soap, but a lot of guys really seem to like it.

Thanks for the info! I've got several tools at my disposal so I should be able to complete trims on my own:
Wahl clippers with several Guards
Small beard trimmer
Manual clippers (heard these are good for beards since they aren't always running)
Professional stainless full size scissors
Small stainless moustache scissors
Hair shaper with guard
 
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