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.

The author’s first OkCupid profile pic. (Evan Wolkenstein)

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.

[6 first-date style tips for women]

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

(Evan Wolkenstein)
  • 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

(Evan Wolkenstein)

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.


How did I improve my dating life? Surprisingly, the answer was in a spreadsheet.

How do you woo someone when you’re still figuring out life?

No tigers. No groups. Not too much skin. How to choose the best photos for your dating profile.