With hindsight, I can admit that this photo looks like a Craigslist Casual Encounters ad gone wrong.
After not hearing from Gabi, I sent a follow-up: “Hey, you seem like a great person,” I wrote. “If you’re not interested, no problem, but I thought I’d check and see if you got my first message.”
What I lacked in online charm, I made up for in persistence. She agreed to a drink; we dated; three years later, we got engaged.
Between the time I took that awful picture and the day we met, I’d learned a lot about style and about dating. I’d learned not meet for dinner on a first date (expensive, too much time, too much pressure). I’d learned that coffee might not be a good idea (feels like an interview). I’d learned that a hike is best saved for date four (when you’re sure you enjoy each other’s company and getting lost in the wilderness together isn’t necessarily a bad thing).
I’d learned about the simple magic of a happy-hour date at an upbeat bar or pub, with a 1.5-hour time limit. I’d learned that confidence is the most attractive accessory. I’d learned that listening is the most important “technique.” And most important, I was learning that even though dating wasn’t coming easily, I was dateable.
I also learned what not to wear on dates:
- Clothes that don’t fit, a.k.a. 90 percent of my old wardrobe.
- Clothes that make it look like you’re trying too hard.
- Clothes that you’ve owned since the Clinton administration. Cargo pants, anyone?
At the time I met Gabi, I’d been taking steps to become my best self: I’d increased exercising, writing, drawing, throwing myself into my work. I would ask my very dapper colleague: Why does that go with that? Can I pull this off?
I learned to correct my style mistakes rather than fear them. As a result, I was more confident, I was better dressed, and I even started to enjoy dating.
Too often, people put too much thought into what to wear — or too little. If you’re not sure, wear your favorite first-date outfit to work on a non-date night and ask a well-dressed colleague for their honest reaction. (Make sure to choose someone who’s already a close confidant.) Read style blogs. Experiment. But if you have a date this Wednesday at 6 p.m., this outfit balances poise and dignity with casual comfort.
The Wednesday happy hour outfit
- Jeans: dark indigo, slim-fitting. Don’t spend a lot of money; grab some Levi’s 514, 511 or 505 for around $60.
- A pair of Clark’s Original Desert Boots. They look good with everything, and at $130, are worth every penny. You can also find them on eBay for about $75.
- A button-down, blue gingham shirt. The horizontal/vertical pattern gives your body structure, but the color and pattern is cheerful. If your workplace isn’t down with denim, swap in some slim-fitting chinos with a chambray shirt.
- A knit tie. You’re coming from work, right? But the knit fabric is casual. Perfect mix.
- If it’s cold out, a classy but cuddly shawl-neck sweater sends just the right message.
The Saturday night, swanky date outfit
Let’s say happy hour No. 1 went well. There was chemistry, banter, a spark. Do not ramp it up immediately. Do not invite your date back to your place to see your collection of artisanal mustard. Instead, send a friendly text that evening, and meet the next week for happy hour No. 2.
And if that goes well, then it’s time to make a reservation at a great restaurant for a Saturday night, the all-important date No. 3. Yes, an actual reservation. And wear something classy; be the best-dressed man in the place. Show your date that you put some thought into this.
- Chinos: The color is up to you, but they should be slim fitting, and never baggy. They shouldn’t bunch up around your shoes, a sign of being too long. If you’re willing to experiment with color, try any of these. If those are out of your khaki-comfort zone, go with grey; it’s classier than the usual tan.
- Pair with one of the shirts from happy-hour, or try a classic oxford cloth button down (sometimes called a OCBD). This is not a dress-shirt; it’s “styley-casual.” The material is thicker, with some natural texture, and it looks great with anything.
- Find a skinny tie (under 2.5 inches wide) in a non-shiny material. If you’re new to the world of the casual tie, Original Penguin (sold through Nordstrom Rack) has your back. They sell for under $20. Stick with a solid if you’re wearing a gingham shirt; or, for your OCBD/chambray shirt, a subtle pattern like this, this or this.
- Once you have your outfit together, head to Zara Men for a blazer in a neutral tone. Get the smallest size you can without it being tight.
The rest is up to you. Be a good listener. Grab the check and say, “My pleasure!” After dinner, go for a walk, hit a dive bar, or head back to your place (which you’ve cleaned, and the toilet seat is down). Be a gentleman. Expect nothing. Follow your date’s cues. And no matter what, text the next day to say thanks for a lovely evening.