Learning to date and learning to dress have a lot in common. Once upon a time, I was terrible at both.

Before I met my fiancee, Gabi, I was single in San Francisco. It was 2011, and everyone was on OkCupid. My first profile was horrible.

Gabi now explains why she ignored my first OkCupid message: If I hadn’t bothered to clean up my laundry, comb my hair, or replace my aged, baggy jeans (vintage 1997), why should she expect me to bring my A-game to a first date?

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

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.

Build your look from the bottom up with the cornerstone of any outfit: shoes. Put on a pair of brown, leather shoes, like these or these. Do not, under any circumstances, wear leather slip-ons.

  • 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 thisthis 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.