Controlling for certain factors such as weather and season of course.
But I also find that there’s also other things that influence my decisions. Like if I DONT want to wear a certain color of boots, or pair of jeans more than I want to wear a certain jacket, I’ll just mix up my jacket rather than wear the boots I don’t want to wear.
8 jackets in Rotation, 2 are “special occasion, kinda babied”, 2 are mainly bike use only or for layering in the cold, remainder are worn most just whatever I feel like wearing that day. 3 of the latter need lots more wear for break in, so they get worn the most…
I only have a few jackets that are leather , but in general with my jackets I pretty much just go with whatever I feel like wearing that day that is practical for the weather ahead.
At my blue collar job I can't wear anything " nice ", so it's just my few days off and occasionally when I'm going to be doing something after work that I get to wear one of the jackets from my closet.
A lot will depend on what I'm doing that day - as well as season, but assuming it's a leather jacket day, then typically I'll pick the jacket based on what works best with what else I'm wearing. I usually start with one particular thing I want to wear, and everything else flows from that. It's usually boots/ shoes up, or hat down. Sometimes I'll dress around a specific jacket. Though in truth I've been wearing leather less often recently. I need to clear out and to some extent start again as a number of my favourite leathers just don't fit me any more. I've lost a lot of weight as to where I was for a few years, but when I try the old jackets on again, it seems that while my waist has shrunk, my shoulders have spread somewhat in the last fifteen years and I now at 50 need a bigger size to accommodate those.
Most of the time for me it is the weather, and the rest of the outfit comes after to flex around the jacket. Like I have a lighter weight jacket that gets a lot of wear just because it's often quite warm where I am, just allows me to extend my jacket wear time out of the year.
I pick out my clothing for the week ahead to lessen my weekday morning rush. The downside is that I don't have the variety looks within the week. Black goes with everything. Other colors needs some planning ahead.
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