It's not exactly clothing but I'm in love with this pair of boots I bought last year. They're not like, heavy duty boots, or rain boots, or really tall boots. Just nice boots that just happen to match my bag (I'm not a purse person but when I noticed this fact I'll admit I found it funny and pointed it out to all my friends). I hate wearing flats and sneakers so even though it's the middle of the summer I still wear them.
And if you see me wearing something other than jeans, something formal is coming up.
In the winter I'm always wearing a hoodie. Our heating system at home is both shit and kept really low, so the house is always freezing, and our school's heating system is mostly broken (one year my Spanish teacher told us it was okay to show up late if we had to grab jackets from our lockers because the heat in her classroom didn't even work at all, and that year they were doing construction on the upper floor, so her room was filled with dust, so she LEFT THE WINDOW OPEN) so that hoodie has become my best friend.