Stay Confident, Date with Style

How to stay confident on dating apps by curating your own personal style

I had spent the majority of my adult life with one person. We met just before I graduated from college—before the world of texting and cell phones. He lived on my block and we met at a mutual friend’s house nearby. That was how dating used to work. A failed marriage and two kids later, I was thrust back into the single world in my early 40’s. When I decided I wanted to try online dating, it was like learning a foreign language. Sure, I tried the old fashioned way: telling my friends to set me up with other friends or colleagues. But that happened twice. In two years. So I quickly realized I had to give online dating a go.

As an art director and stylist, with over 15 years of making things look appealing, I caught on pretty quickly on how to present my photos and bio to get the most out of online dating. Many of my friends and a lot of the guys I dated, on the other hand, struggled to represent themselves accurately with their dating profiles. I went out on dates with people whose profile photos weren’t that great only to find that they were much more attractive in person. Or, their bio read like a boring resume, but when we met in real life, they were actually super interesting. In my new single life, I encountered a world of people challenged to find love online, and also my true calling as an online dating profile stylist.

Most people I work with haven’t updated their look in quite some time and are shocked at how different they feel after. Whether it’s editing what they already own and putting new things together or going for a full day shopping trip, the results are similar—they feel more confident. When you feel more confident, it shows on the outside. In your profile pictures and real life.

Here are a few of my tips for boosting your confidence out in the dating world:

Own your level of style savvy
Don’t feel you need to veer into trends. Embrace where you are in life, career, and family, and buy clothes for THAT person, not for someone you think you might become. When I first became single again, I bought a slew of fancier dresses and skirts because, in my mind, I was going to start going to cocktail parties all the time. Guess what? I didn’t go to any! And those clothes ended up getting consigned at some point.

Keep it classic and simple
When in doubt, go with a mainly black, white, and grey palette and add in color from there with shoes and accessories. When you don’t have time to put into shopping and fashion, this is an easy, timeless way of dressing.

Incorporate 6-8 new pieces per season
It really makes a difference as far as keeping up to date on your look and not letting your look become stale over the year. I suggest two pairs of shoes, four or five new clothing items, and at least one new accessory each season to stay fresh. This updating also goes for your profile photos. Keep those updated and swap out for pictures wearing your new clothes at least every six months, or even better, each season.

Consider consulting a personal stylist
More and more people (not just the rich and famous!) are hiring a stylist to help them edit and organize their wardrobe, shop for some new pieces, or spark some new ideas. It can increase your confidence, help you get a new job, or feel good on that first date. Either look to your local community or some stylists do video consults.

Founder of Style my Profile NYC, Alyssa Dineen is an NYC stylist and online dating expert

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