Clothes are hard, Total beginner

I’m 39 and want to dress well. I’ve always been a hoodie and jeans kinda guy, and got away with it through a career in youth work. I recently started a new life philosophy and want to dress to reflect that.

Growing up my family was poor, and had no time to teach me things about presentation. My dad never taught me to shave, my parents never bought me a shirt for high school formals. So I got a chip on my shoulder on how I look, endured many shameful social events, and chose to have dreadlocks for 15 years as a fuck you to the social pressures I was failing.

My new philosophy is to get the fuck over myself, learn these things I never did now, and enjoy their benefits! I’ve got an amazing stylish girlfriend and she will enjoy shopping with me. She’s amazing because despite her high standards for her own presentation, I’ve never felt shame around her, just encouragement. How good is a good woman! She does laugh at old photos of me with the dreads though :D

I also have adhd and get overwhelmed at all the categories clothing is in, in terms of brain space. Seasons changing warmth/comfort etc, Shrinkage wear and tear, so, smart use of dryers/storage space etc, Style, and all the different social settings and the expectations they bring, Not to mention dollar cost, time spent shopping, dealing with online returns for shit that didn’t fit, the ethics of the company, and does it make my skin feel weird!

Anyone wanna be my consultant? 😅

I find it hard to break it all down into manageable decisions. What’s a good way to progress?