Forewarning, this is a bit meandering with a whole bunch of "I" statements:
So in my mind I feel like I want to dress more feminine, or feel like a should. It's be complicated to explain. I'm trying to be more social, going to new events and different groups to meet more people. A good chunk of my friends are paired up now, and some have kids.
So I think I need to be a bit more approachable, if that makes sense.
But then last night I place this order from H&M, which fits with my current and past style, but really isn't feminine. Notice I didn't get a boho blouse like was thinking in my outfit from Saturday. Old habits die hard I guess. Or maybe I'm trying to force myself in a box that doesn't work.
Age is becoming a factor as well. Some of the events I've been to are way heavy on the 20-somethings.
I'm also trying to be more aware of how and where I will wear such things, including trying to find things at lower price points. So the black boxing shorts are a bit of a stretch for practicality and wearability; honestly they may not fit as the sizing wasn't matched with H&M size suggestions. I did choose the white hoodie over the black though (Clorox bleach crystals are great BTW). Also tried to think about how they'd mix with existing wardrobe pieces.

ETA I did get a small 15% discount through some random code, which pushed to order a bit more.

H&M
Leather Waist Bag
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2
H&M
Cycling Shorts
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2