Dressing for the Post Divorce Date

This is David’s article written for the Huffington Post:


Divorce is hard no matter how it transpires. But just like leaving one job and starting another, the downtime between ending a marriage and seeking a new person is the perfect time to regroup, refresh and reevaluate. It is a rare and wonderful occurrence when we have the opportunity to objectively look at ourselves and decipher where we are, who we are and what we want going forward.

Besides looking at your career, living situation, goals, dreams and desires, one thing that should be looked at that can have a profound impact on all of the elements of your new life is your personal style.

As you reenter the dating scene, your style is going to brand you and make a very strong impression. How you show up for a date will not only telegraph visual clues about who you are, but may even impact how the date goes and influence whether or not there is a second one.

Let me relay the cautionary tale of Brenda. Vivacious, gorgeous and smart, Brenda both married and divorced young. One afternoon post-divorce, we enjoyed lunch at her apartment. Over dessert, she shared that she was off shortly to a blind coffee date. I was thrilled for her until she disappeared into the other room and appeared in what was intended to be her date outfit. Brenda had replaced her cute cotton sundress with a pair of ill-fitting jeans, a faded t-shirt and scuffed boots. It also looked as if she had removed much of her make-up. I think my stare said it all. She looked down and said, “I don’t want it to look like I am trying too hard.” She wore this ensemble on her date. Needless to say, even though she was interested, there was never a second date. Perhaps there was nothing in common. But perhaps her date was turned off by the bizarre, disheveled ensemble she chose to wear for her unveiling and his first impression. I can not help but wonder if he was the guy for her and her style choice was the reason she didn’t land a second date.

We are a visual society, and the first impression others have of you at a job interview, party or first date is purely visual. If you are thinking, “But I want people to like me for me, not for the way I dress,” you are greatly limiting yourself. Why not be the big brain who is also attractive and well put together? A date’s first impression is always going to be visual.

Before I divulge what you should wear on your first post-divorce date, I am going to ask you to do a little style check. Ask yourself if the clothes on your body reflect who you are today — not a year ago, but right now. Do the words that you would use to describe the clothes in your closet also accurately describe your personality? Is what you choose to wear really flattering, or is it something that worked a long time ago and you have not bothered to change the formula? Are you dressing yourself or merely covering your body? What once suited you perfectly before and during your marriage might not work for you now.

As you start to think specifically about what to wear on your first post-divorce date, the very first rule is to never wear an outfit that you wore at any point with your ex. Now is the time for creating new memories without that person. It is of the utmost importance that your first impression on a date is as an open, sexy, confident person — someone your date would like to get to know. I suggest buying something new to celebrate this new beginning. Unlike Brenda, you need to put out a romantic vibe, so use a romantic color.

Your individual romantic color, or personal version of red, is your sexy color. The warm passionate glow from this hue gives the perfect welcoming impression on a first date with the person whom you might possibly spend the rest of your life with. Here is the way to discover yours, regardless of your skin tone:

1. In natural light, hold your hand over a white piece of paper with your palm facing you. Curl your fingers so that your palm is “cupped.”

2. Look carefully at the most flushed areas of your palm and notice the shade.

3. Now, pinch the fingerprint (non-nail side) of your index finger with the other hand. What is the color of your flushed skin? Possible candidates include raspberry, brick, tangerine, cherry, rust, burgundy, crimson, shell pink, fuchsia, etc.

Note: You will find your romantic color at the cosmetics counter in your local department store. It is often easier to see this color more clearly if you hold your pinched finger next to a tube of lipstick or blush.

Now it’s time to use that color. After you have discerned which clothes in your closet accurately capture the you of today, use the fabrics, cuts and silhouettes that you find there as a shopping guide for your date outfit. These garments which you enjoy wearing the most and receive the most compliments on are the perfect items to find in your romantic color.


Men can wear their romantic color in a shirt, tie or sweater. For a woman, try a blouse or dress. A non-patterned or simply patterned garment in this color is best as there is no chance of a pattern pulling focus from your face. Also, your date will hopefully be concentrating on parts of your body that are viewable from across a table. Therefore, the right neckline in your romantic color is key. If you are wondering which one suits you best, simply follow the shape of your chin. A man with a more angular jaw is best in a v-neck sweater while a woman with an oval chin looks fantastic in a scoop neckline. To figure this out, test existing garments or draw shapes on paper to discern which is the most flattering.

There is, of course, no guarantee that your first post-divorce date is going to be with the one. But if he or she is the perfect person for you, you are going to be ready (unlike Brenda, who unfortunately still hasn’t figured it out) when you visually come across as the most radiant, sexy and powerful version of yourself.