Shopping for Construction Boots and Dickies

I'm caught in the in-betweens.  I've psychologically shifted my sense of style, but physically my wardrobe isn't there yet.  It takes time to find just the right pieces, especially when you're thrifting.  And if you're buying new pieces, the financial pressure is on not to fuck it up.  I recently bought 4 thrifted items: the oft-mentioned men's pants, a green corduroy button-down, a blue T-shirt, and a burgundy shawl-style cardigan.  I've been wearing these items in constant rotation, but the pants are problematic without appropriate footwear- and a belt.  So I went to one of those horrible stores where they sell men's workwear (like construction work, not office work) and picked out a pair of "logger boots."  They have a slight heel, which apparently all logger boots do, but they are in fact men's, size 7.5.  They're a beautiful mid-brown leather with black soles and they lace up above the ankle- they’re referred to as an 8” high boot, and the brand is Carolina.  I've put the boots through a rigorous testing process: I walked on our treadmill in the boots for an hour- twice.  They passed with flying colors- no blisters or bunion pain- but I've been having some hesitation about committing to them and wearing them outside.  My hesitation is the heel.  Are they too feminine?  Could they be mistaken for women's boots?  If so, this would really bother me.  The whole idea with this style shift is to really adopt a more masculine look, especially in terms of pants and boots, and to escape the traditionally feminine aesthetic.  To escape the arbitrary sizing and cheap fabrics and infantilizing nature of so much women's clothing.  But I do really love the boots.  So I'm torn.  All this indecision has been stalling my personal style transition.  So today I took the bull by the horns and went back to "Bob's Stores" and found another option.  They of course need to go through the rigorous testing process, but they are a more traditional men's flat work boot.  They're the classic 6" high Timberland Pro work boot in all black leather.  I also picked out a black leather belt (I returned the faux leather brown one to Marshall's) and returned a pair of "Dickies" men's work/uniform pants.  I had picked them up at Bob’s when I got the logger boots, but I decided the poly-blend fabric was a little too sweaty for my liking.  So the boot decision is still in process, but I do have a belt to wear with the pants I thrifted.  I'll just wear them with my knee-high Sorel boots like I have been.  This whole process is making me very impatient- like I'm actually feeling embarrassed to wear my skinny jeans and women's ankle boots.  I feel like I look middle-aged and of little consequence.  But these new boots are not cheap- about $135 a pair- and while neither belt was very expensive, I couldn't bear to take the tags off of the faux leather one because I don't want to settle.  Buying new things- probably made in sweatshops, because apparently everything is- is already questionable behavior in my mind.  So holding out for just the right item seems like the least I can do when I can't find something at the thrift store.  Now I was pleasantly surprised to note that some Carolina brand items are actually "Made in USA," a fact that is causing this "Bob's Store" to grow on me.  I'm sure union factory workers who shop for these types of clothes would prefer to buy items "Made in USA" based on principle, and the store’s stock may reflect that.  (Looking into Timberland's labor ethics reveals that they also offer some “Made in USA” products, and that they do report a decent rating on their factories from a 3rd party- not that that necessarily means anything). But the other reason Bob's is growing on me is that I don't feel bad about myself when trying to find my size there.  With the belt, I simply looked at the tags to find the correct measurement (42") for my mid-hip area where I wear my pants.  No judgement or inherent comparison, just a  measurement.  I'm sure plenty of men bigger than me shop there and are able to find their size.  And trying on boots, I actually found pairs that were too small for me- apparently smaller men can shop there, too.  And there was never any intimidation factor ("Um, little lady, I think you're in the wrong department").  Nothing like that.  I love how utilitarian the whole place is.  Now I like looking at pretty things just as much as the next woman, but it's refreshing to shop without trying to fit into a smaller size or wondering if a pair of boots will last more than one wear. Because, did I even mention, the QUALITY of men's clothes?  For the same (or lower) prices we women pay for basics, men are getting something that will withstand years of wear while we are getting frilly tops that fall apart the first time through the wash.  All the more reason for me to consider menswear.  The clothes have great structural integrity.  And whether or not it’s true, I think I look like I have more integrity when I wear them.