What looks good at 22 rarely holds up after a mortgage, a meltdown, and a midsection.
When I was seventeen, I got my first pair of Cole Haans: the tucker venetian. Not only were they amazingly comfortable, but they marked the incipience of my personal style journey. During my college years I vacillated between preppy and something I’m going to call elite grunge. It didn’t go well. Once I started teaching, I’d found my stride, and I was a full-blown prep: khakis, loafers, tie, jacket. People started to know me as the guy who overdressed at work, and I prided myself on my sartorial game being a step above the fray.
But then I had a daughter, went through a divorce, was a single dad, started dating, got remarried, had more kids. And through all of this, my personal style changed.
Now that I’m nearly 39, an exhausted dad, a seasoned teacher, and euphorically married, my aesthetic has evolved.
Here are some things I’ve learned along the way; maybe you can relate.
I Don’t Dress to Impress
When I student taught, I had a tenth-grader who noticed one day that my socks perfectly matched my tie. She pointed it out, and this became a somewhat playful signature of mine. It made the kids laugh, and I actually came to enjoy the coordination. By the time I got my first teaching job, it was seared into my mind that people were paying attention to how I dressed, and I wasn’t going to be the man to disappoint.
Over time I’ve realized that early in my career I paid more attention to how I dressed than to whether or not I was actually an effective teacher. Now when I get dressed in the morning, I focus on wearing an outfit that will make me physically comfortable and let me feel good about myself aesthetically; whether or not anyone else will notice isn’t my concern.
Personal Hygiene is Part of Your Personal Style
A few years back I had a student who was struggling to get the ladies to notice him. After class one day, he told me he’d started ironing his polos and khakis (my school’s uniform) before school and was trying to put himself out there more in conversations. But girls weren’t interested in talking to him.
That’s when the conversation got real. We had an honest chat about hair washing, face washing, shaving, and nail clipping, none of which he was doing on a regular basis. I told him that he didn’t need to become a cosmetologist (which I had to define), but some basic hygienic upkeep makes all the difference when it comes to what my kids call that rizz game.
The fact is that the significance of hygiene transcends simply flirting; no one is going to pay attention to your boardroom presentation if your hair is greasy, and the boss doesn’t give the promotion to the guy with the oddly long fingernails.
Dress the Body You Have
When I started teaching, I had a 30-inch waist. Seventeen years later, I’m more like a 32-33 depending on the pants. For a long time, I fought the way my body had changed – sure I’ve gained some weight, but I can still squeeze into those 30s! Have you ever seen an overfilled sausage, trying desperately to burst out of its casing? That was me.
There are two problems with wearing clothing that’s too tight:
1. It’s not comfortable.
My job requires me to move around the room, crouch down to check on students and get involved in group work. The last thing I need is for a hastily-sewn pants button to go flying across the room with the velocity of a bullet because I put too much strain on it. I’d rather wear pants and fit the waist I have and know that I’m safe to move comfortably.
2. You’re not fooling anyone.
Do car salesmen actually think they’ve fooled the world into believing they all have huge biceps? Like…we all know those button-down short-sleeve shirts are just two sizes too small, right? Here’s the point, when your clothing is too tight, it doesn’t make you look svelte: it makes you look like when Tommy puts on Richard’s jacket and starts singing Fat guy in a little coat. And if you’re too young for that reference, here.
Buy the Better Product and Create Less Waste
I’ve know we’ve written about this quite a bit, but the older I get, the more I embrace the cry once philosophy. I’ve had the same pair of loafers for over ten years. I still have three dress shirts that I bought my first year of teaching, and I’ve carried the same leather bag since I was 22. This isn’t to say that I don’t enjoy getting new stuff; hell, I love new stuff. But whatever I acquire, I try to get the best that I can afford so that it won’t have to be replaced in six months.
And to be clear, the best I can afford doesn’t have to mean the most expensive. A perfect example of this is my undershirts: Walmart’s house brand of undershirts (George) is fantastic. They don’t shrink, and the cotton is the perfect weight. I can afford them, and they’re the best I’ve found.
Dressing Beneath the Occasion Isn’t Cool
Inasmuch as I’ve left “dress to impress” behind for the younger dudes, I still dress appropriate to the occasion. A full suit doesn’t make sense in my job, but neither does a t-shirt. Recently my wife and I went to a wedding, and I couldn’t believe how many guys were wearing slacks and a dress shirt but no tie or jacket. And hey, I’m not saying they needed to wear a tie and a jacket, but they could’ve at least worn one or the other.
Overdressing connotes pomposity, but underdressing says something about how seriously you’re taking the event at hand. Sneakers on a Friday? Sure. Sneakers to a wedding? No sir. Untucked shirt in the office? Probably fine. Untucked shirt for an interview. Good luck.
A Small Pop of Color Goes a Long Way
I remember when I got my first pair of salmon-colored pants. It was the great chino wave of 2012, and baby I rode the wave. Salmon, royal blue, baby pink, algae green – I had them all (and still do). I love color, but over the years I’ve found that a small pop of color often makes as big of an impact as a statement piece like those baby pink pants.
A pocket square, scarf, floral tie, or even a saturated watch band will often add that extra edge an outfit needs. There’s power in subtlety.
