What to Wear on a First Date After Divorce.

first date
How to choose a first date outfit? Simple: opt for something flattering, but comfortable.

In the online dating era, your potential soulmate is literally a swipe away. A well-thought-out bio, a catchy profile picture and a great outfit, can actually pique their interest enough to say yes to that first date.

That’s not an easy feat.

Especially if last time you went of a date was decades ago and the concept of finding love via internet is as foreign to you as walking on Mars.

That used to be the case for Alyssa Dineen.

After her marriage of 20 years ended, Dineen, a New York fashion stylist, had to learn how to navigate the dating world.

It didn’t take her long to realize that many people were doing a poor job at presenting themselves, when, in fact, they were ‘totally normal in person’.

“But you would think, “Why haven’t they run that by somebody first?’,” Dineen said referring to their wacky profiles.

Things worked out for her; Dineen met her current boyfriend on Tinder.

Later, they started brainstorming ways to help people ace their online dating game. That’s when Style My Profile was born. Through this service, Dineen helps with bios, photographs and styling for online profiles, so that her clients can attract the right kind of people they want in their life.

Most of her clients, Dineen said, are divorced and haven’t dated in 10 or more years.

Alyssa Dineen

They just need hand-holding. I think it is just the fear of the unknown. I’m 45, and it’s completely new to everyone.

Here’s how Style My Profile works:

  • If you need a help with your bio, she begins with a ‘bio cheat sheet’ with prompts and questions to think about when writing it. She also offers tips on how to make it sound as ‘unique, interesting and inviting’ as possible.
  • When it comes to photos, Dineen helps with either selecting photos you already have or taking new ones.
  • For the wardrobe overhaul, Dineen may do an in-person shopping session and style your outfits appropriately for first dates.


Read Dineen’s tried-and-true tips to elevate your online dating game:

On how to create the most striking photos:

From my background and experience in styling, I work with men and women, the personal styling and the transformation that happens with people when they wear something that really flatters them, looks good on them, and makes them feel good. It is so tangible you can feel it. You can feel how good they feel. It sounds silly but it can be as simple as a pair of jeans that they look and feel good in.

The new pieces in your wardrobe and pictures of this ‘new you’ come through and you can really see the difference in somebody. I don’t even mean getting a whole new makeover, sometimes just changing a few little things is enough to make a huge difference.

Make sure your photos are very clear, that you’re not cropping somebody in or out and that you’re looking at the camera. It’s important to be engaging and facing the camera looking head on.

On how to master the art of the selfie:

Unless you’re really going to practice for a long time taking selfies, I disagree with taking selfies if you’re my age or older. Unless you practice it and are really good at it, have your friend or somebody else take photos of you.

Style collage


First date outfit ideas for women:

  • Wear a nice flattering top and simple jewelry. If you’re going to be sitting at a table, then your date is only really going to be seeing the top half of you.
  • Wear a pair of great fitting jeans.
  • The goal is to be and dress as comfortable as possible. You don’t want to be fussing with your clothes on the first date.
  • Heels are okay, but comfortable shoes that also look good are always important too.

First date outfit ideas for men:

  • Find a happy medium between dressy and casual.]
  • Don’t wear a ratty old t-shirt and sweatpants. You want to look put together.
  • Don’t wear suites.

Read more tips on online dating:


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