The first pair that I ever owned are my black boots. My friends found them for me one day when they were at Value Village. They were only 14 bucks, they were my size, and they were in next to mint condition. I had to literally beat them with a hammer to stretch them and wear them out, but they fit like a glove. I wear them almost daily and I've worn them in the snow and cold, and I've worn them in the heat and humidity. They are without a doubt my go to boots and it's rare to see me without them. My feet can barely stand wearing anything else because they're just so comfortable. Some days I do switch it up though and wear my shoes by Dr. Martens. I bought my doc shoes off of somebody I know; she was looking to get rid of them and she knew I was desperately looking for a pair and bam, $20 later, they were mine. I love them and I generally wear them with outfits that don't really go with boots but I still need to comfort of docs. My most recent pair came into my work (I work in a consignment shop) on Monday. They're mint condition black velvet floral docs with a thinner sole, and they're so perfect I could cry. They're super comfortable and they aren't as bulky as my pair of Dr. Martens boots. I couldn't believe my eyes after seeing the price tag of only $40, I knew they had to come home with me.
All pictures were taken by me. This post is in no way affiliated with Dr. Martens, all thoughts are my own.