I say do whatever makes YOU and YOUR horse happy But letting him grow a coat will help him...

I had an arabian mare that I got when I was 10 (she was 8). Not the smartest move that my parents ever made.. lol but she did help me through my teenage years.. after all the broken bones she gave me....
When I was 14 we moved from Cali to Virginia and I refused to go without her $1k later to move my $800 horse... lol I felt really bad for her since I know I was freezing from the temp change! I got a few blankets for her. I only had a light fleece like blanket before to keep the winter fur down (I showed at small shows) I had the full hood and everything! And I learned the dark colors were a BAD idea! I guess she noticed she was now pretty much invisable at night (she was grey) so i'd go out to feed her at night searching for trees to find my way to the barn in the dark and EVERY night i'd here the sounds of galloping hoofs right in front of me and coming at me. I started to just stand there and wait for it. The slide stop and the heavy snort in my face. lol
She had so much personality! I loved that horse!

BUT yea... I'm sure he'll learn to live with not having it (i'm sure rolling is much more enjoyable without a blanket). But i'd for sure keep one on him in cold weather!
Just do what you wanna do!

I always had stall and pasture during the day for my horses.
Now i have none

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Finding horses in the dark. Haha! My carriage horse was the only one with white on his face. I called it his 'headlight' cause it made him the easiest to find in the dark.

The 3 we have now are all dark bays who turn nearly black with their winter coats. They're hard to find in the summer, especially when they go way out back and graze in the shadow of the tree line, but standout very well against the snow in winter.