For the very typical straight male, there are two things that will incite an extreme divergence in personal fashion. 
One is a new job.
The other, obviously, is a new girlfriend.

For me, it all converged at once.  I started dating a girl who, as much as she liked that I wasn’t a suit, always partly wanted to see what I might look like if I put on something a little more upscale.  It wasn’t that she wanted to turn me into an investment banker, but she did want to know that I could pull it off if I had to. 
I had the sense that she liked the fact that I could simply towel off after a shower, put on a clean t-shirt, and be ready for the day.  Maybe it implied youth or incited nostalgia.  But being over thirty, she understandably thought it equally appropriate to be dating a man, not just a boy.

Shortly after we began dating, I took on a new job.  I went from days on the construction site to days in boardrooms meeting with clients.  My wardrobe was going to have to change accordingly.  Jeans with rips and grease stains would have to be replaced with jeans that fit confidently.  My “good pair of jeans” were suddenly insufficient.  I would need more button down shirts. The ones that languished in my closet were ten years old, kept mostly for sentimental reasons and worn only on “special occasions” such as to the weddings of very distant relatives and to company Christmas parties.  I could wear sneakers, but they couldn’t have ollie burns in them.  My construction boots would have to give way to combat boots, maintained with a polished black sheen.

Then there were the hygiene products.  When I was working in construction, I never took care of my skin.  It just wasn’t done.  But my girlfriend and my job made me aware that razor burn was not a “look” and that there was something both alluring and relaxing about the soothing aromatherapy of moisturizers and specialized soaps.  One day she took me to a specialty shop where an erudite clerk guided me through a whole new regimen of products, all of which now line my bathroom sink counter and shower.

Transformation is a gradual process.  It starts with an idea of who you want to become.  Eventually you see yourself in a different way, and you become a new kind of person.

Stay tuned for Part 3  –  Advanced Level Fanciness