Nursing a hangover, I landed at New York’s LaGuardia airport during a snowstorm. It was March 1, 2015. 12hours prior I had been in northern Wisconsin, drinking too many beers too fast on the heels of a solo cross-country trip from Los Angeles to Wisconsin. My eight-year relationship had ended, and I wanted to move back to Brooklyn. That morning, one of my friends drove as I spent the ride to the airport drinking black coffee and attempting to keep down hash browns.
After dropping my bags in a windowless Williamsburg sublet, an old friend took me out to catch up. As we trudged through the busy snowy silence, he talked-up dating in New York. It’s full of so many awesome women, he said. You’re going to love it.
Rounding a corner, we ran into a woman who was waiting outside the Metropolitan Avenue G subway stop for a Brad Johnson from Tinder. I stared, taken aback. Was this a joke orchestrated by my friend to make newly-single and still-heartbroken me feel better? Was it a sign? I decided neither and ruminated with my feelings. What I wanted was a hug.
My friend and I ate at a small diner as the snow fell outside. Feet numb and sopping wet, I recounted my heartbreak: while I wasn’t going to fight it, my ex got the dog and revealed her feelings for a mutual friend.
After dinner, my former college roommate met us for a drink, and when I saw his artic-survival-ready coat, it hit me: I had nothing warm to wear. I wasn’t ready for the remaining months of winter. I needed a warmer coat, gloves, long underwear, real socks. Everything. I leaned back, looking at the two of them dressed rather well. I felt too relaxed in my clothes. Out of place.
My journey with clothes may seem familiar: I barely used to think about it. In high school, I rotated between band shirts and tees with oh-so-witty sayings. My hair resembled a thick mop, and my glasses were ever-sliding down my face. After a high school girlfriend had convinced me to take part in a trend of wearing women’s jeans from American Eagle, I realized I wasn’t being true to myself and stopped taking fashion advice.
My youth had been filled with patched, oversized hand-me-downs. The first two years of college weren’t any different. I started to wear cardigans but became self-conscious when a professor thirty years older wore the same sweater on the same day as me. I still remember the image of me, mortified, as I subtly put the sweater into my backpack, hoping no one noticed.
Things started to click in 2009 when I was a junior in college. I had never been to New York before but decided on a whim that transferring colleges was what I wanted to do. I wore baggy shorts and tie-dye shirts on the regular.
It took about a day in the city to realize I needed a new wardrobe. The streets of New York are full of well-dressed people; a big difference from the dad jeans and oversized t-shirts standard in Wisconsin. Lost, I subscribed to a male lifestyle magazine and started using Pinterest, an image-sharing website where users pin photos to their personal profile. These became my go-to for inspiration with the occasional peppering of Tumblr, another image-sharing blog. I didn’t want to wear what everyone else was. I wanted to wear what I liked, which turned out to be a more classic, blue-collar style most likely influenced by my life in Wisconsin. Little by little, I started to wear button-ups and plaids and searched for jeans that fit.
Welcome to Winter
It was late. I collapsed onto a mattress that was too small for me. The pangs of loneliness crept up. As I looked up at the ceiling, able to hear every movement through my paper thin walls, I decided New York meant a whole new beginning. Going through a breakup was a necessary torture, but finding myself at the other end was an exciting prospect.
Moving helped me do one usually difficult thing: purge my belongings. I could only get on the plane with whatever carry-ons I had, and there was the bag fee (which I later learned grows exponentially after a certain number of bags.) I bungee-corded four rolling suitcases together with my full backpack. It had everything: laptop, sheets, towels, clothes. My new paired-down life. I had found the warm essentials quickly but paused on staples. Was I going to be at a job that required a suit, or just jeans and a t-shirt?
I was a mess. For months, I was a wallflower on nights out. Winter melted to spring, and after an ill-fated attempt to woo a former college classmate, my guy friends told me I had become pathetic. They said, just pick someone up while we’re out or download a dating app. The problem was, I had no idea how to date again. Apps had become the norm while I was in a relationship. I needed advice.
Knowing my male friends would tell me not to overthink and just date, I turned to my female friends. They recounted their relationship experiences, ranging from dating is the worst to all guys are awful. Many sighs about being open, honest and forward only to be let down. Dating sounded terrible; I shied away.
Suddenly it’s Summer
Summer arrived. Walking through Tribeca on a Sunday afternoon, a friend had grown sick of my relationship questions. She made me promise to download some apps and go on a date. Just dress like you care and be nice, she said. I nodded, overwhelmed.
Her advice became something I took to heart. I had been in New York for a few months, and my personal sense of style had changed. I consider myself someone who likes classic apparel—usually unbranded (I de-stitch logo tags when I can.) solid tees, plain sweatshirts, jeans that fit and sneakers or boots. Today, my go-to for online deals can be Reddit’s Frugal Male Fashion subreddit. Their Male Fashion Advice is useful for tips, but I try to take everything with a bit of doubt. It’s best to go into situations knowing the kind of look you like best and adjust. But sometimes you need a jumping off point. It’s like a mix and match style. It takes a few good days of standing in fitting room lines holding six pairs of the same pants in different sizes, but it’s worth it. In the moment, it was a nightmare.
Jumping in With Both Feet
I made a profile. After a bunch of trial-and-error with women not replying or me talking too much that any chance at a date fizzled out (set up a date right away, or you become internet pen pals,) it happened.
First dates feel like job interviews to me. I don’t know the person, and however much we’ve communicated online, real life is different. We’re in front of each other actually talking. Moments of silence last a lifetime. To help, I usually wore my favorite jeans and a plaid—the clothes that make me feel most confident.
On the first date, I met a woman at a coffee shop only to find out she hated coffee. Another time, I innocently walked someone home, which probably sent mixed signals. Summer progressed. I kept at it and learned from each new experience. I fell off someone’s bed and hit my head on the corner of her night stand. I thought I met my soulmate at a lower east side bar during a midafternoon drinking tour. Subway onlookers eavesdropped as a date’s hands enveloped my body and mused about her terrible dating experiences.
While it felt like a meaningful adventure to have, there was something odd: the dates complimented my clothes. That had never happened to me before. I didn’t get it, so I asked. Turns out, most of the guys they dated dressed like schlubs.
After their stories, I started to notice it with my guy friends. While I had been thinking about what to wear, many of my friends had coasted. They wore bland outfits on dates such as worn loafers and ill-fitting pants. They regularly ran out the door after rinsing only half their body. I can’t understand why spending a little time on finding what you like to wear is a bad thing. Women look great on first dates. They’ve usually applied makeup, styled their hair, chosen a thoughtful outfit. But guys? Nope. Our culture has come to accept smelling like sweat, having messy hair and dressing down as manly. I can throw on sweatpants, beat up tennis shoes, a wrinkled shirt, and I am fine. Most women would applaud fitted jeans and a t-shirt. Maybe a button up. That’s the easiest outfit in the universe. Anything over that, and it’s like extra credit.
I continue to evaluate my clothes and check for inspiration. Lately, I’ve wanted to buy a baseball cap, but can’t decide on which. For me, fashion and dating are a constant state of feeling of self-conscious. Ignoring seasonal noise and ever-changing trends, simple outfits will work forever, and that’s why I like them. Right after I moved, and while I was applying for jobs, a friend told me that no matter what, I should feel confident in what I wear to an interview. The best clothes won’t change the vibe you give off unless you’re confident wearing them. To me, it helps to put my best foot forward like this in all aspects of my life. Thanks to finding what I felt most confident wearing, my personal and professional life has flourished because of my attitude.