I've been slowly getting rid of my awful business casual wardrobe since I quit my office job earlier this year — it mostly consisted of cheaply made gingham and oxford button downs, ill-fitting slacks, and nondescript "first big boy job" dress shoes — and I've been replacing them with casual basic pieces that I can easily wear in my day to day life.
My favorite recent purchase is probably the Brandon Heavy Tee from Saturdays Surf NYC ($60). From someone who's gone through countless Hanes basic black tees, up until very recently I'd never in my life justify buying a $60 plain black t shirt. This shirt, however, is thick, heavy, drapes my torso in a way that is much more flattering, and the material feels absolutely amazing. The first night wearing it out, I got a lot of compliments and a couple of girl friends kept rubbing my back to feel the velvety finish of the material.
I grew up in a household where we had to make clothes last — a huge splurge for me growing up was buying a pair of basic Dr. Martens boots, and most of my clothes came from lower-tier brands at department stores like JC Penney, Marshalls, and Sears. Since moving to New York 4 years ago I've realized that the clothes I'm wearing makes a HUGE impression on people, which is obvious to a lot of people, but it's something I never really took to heart.
For a really cingry example: the first month I lived in NYC, a couple of friends of mine who were working at Alexander Wang as interns invited me to go out to a really trendy bar in the East Village where The Strokes were known to hang out — imagine how out of place I felt when I saw most dudes there were wearing Saint Laurent leather jackets, black Acne skinny jeans, and Rick Owens dunks, whereas I was wearing an off-the-rack business casual suit from Men's Wearhouse and an awful tie. I was turned away from the door, though my friends convinced the door guy I was "cool" and so I eventually got in.
So now I'm slowly acquiring understated casual pieces that fit my day to day life as a fashion photographer living in NYC. My next big splurge is a really comfy Helmut Lang sweatshirt, and maybe a pair of SLP chelsea boots (though I've yet to see a big guy like me pull it off well, unfortunately). Besides looking better, the construction of these pieces will hopefully outlast the cheaper products I'm used to purchasing.
And while this doesn't keep in line with my frugal mentality at first glance, it's actually cheaper in the long run to invest in well-made clothes. There's an essay or theory I read a while back that talks about rich men who can buy a $500 pair of boots that will last him 10 years (maybe longer, with proper care and a cobbler who can resole the shoes when they start to falter), while a poor man can only afford a $50 pair of boots that will last him only 1-2 years. In 10 years time the poor man has spent twice as much money on boots but has had a worse experience.
I've got a LOT of work to do to get my wardrobe up to par with the people I've been working with, but I'm really excited to finally make this upgrade in the coming months.