


I feel really stupid posting this and very self conscious. I’m not used to asking for advice about my looks. I’m growing out my hair again, and I’m at the tail end of the “awkward” phase. My company has thankfully been very gracious and tolerant of this. They’ve even been OK with me wearing hats during this time.
I’ve grown my hair out a few times over the last 25 years, but at some point, I end up cutting it because I’m embarrassed and I feel like I look stupid. I just turned 47, and I’ve been taking Finasteride and using minoxidil to help fill things in. It’s been amazing for filling in my thin patches, and I really want to be one of those guys that looks natural and effortless- like someone who rolled out of bed, tied it up, and went to the office. Messy, but still maintained. My wife says it looks good, and even though her opinion matters most to me, I feel like she has to be somewhat biased.
I think I’ve mostly passed the worst part of the awkward phase, and it’s only just now getting to the point where I can tie it up. Still not where I want it to be, but it’s a huge milestone for me.
Any suggestions with what I could do at this length? I’ve been wearing it down a lot lately because it’s not QUITE long enough to put it up, but I’ve been trying. Only a few hair strands stick out when it’s up, so I just tuck them back.
I feel really self conscious about it, but this is something I’ve always wanted to do. Like I said, I’ve grown it out a few times, but never as long as I really want it to be.
Note: my hair is also very fine, so difficult to manage.