For a dating comeback, we advise a new style strategy.

Dear Toni, 

My best friend is going through a sudden and nasty divorce. This took me by surprise, but I’m comforted by the fact that this amazing woman will surely find love again one day. 

As her closest friend, I’ve promised to help her move on. The problem is that I’ve been married myself for years, and I don’t even know how the dating world works anymore!  What I do know (or at least I think I know) is that single men aren’t scoping out the woman wearing faded jeans, espadrilles, and pink lipstick, like when we were last on the market. Toni, can you help my friend on this journey from frumpy divorcée to fabulous single?

DD

DD,

I will begin by advising that defunct possessions need to be purged at least once a year by all women – married and single alike.  Now, that doesn’t mean old clothes and shoes can’t find a new life somewhere else, but in their current location, stale items run the risk of souring your whole look.

When contemplating whether something needs to stay or go, one must ask herself two questions: (1)When was the last time I wore this item? and (2) Will I ever wear it again? If the answer is greater than two years to the former, and unlikely for the latter, it’s time to go separate ways. Once the closet is cleaned, the real work can begin.

Remember, just as there are love languages spoken between the two sexes, so exists fashion communication. What we wear speaks volumes, before we even utter a word.

In fact, the garments often loved by women are loathed by men. That’s fine when women want to dress for compliments from other women, but they need to understand that the same female compliment-garnering frock could mean disinterest from a male prospect. In order to differentiate between the two, let’s examine some current trends.

My examples below will show how easily an outfit can become a date-dashing don’t.  But have no fear – I’ll show you how to take those don’ts and make them do’s.

The Casual Boyfriend Look

LEFT: She may feel comfy in her bulky sweater, flats, and nerdy topknot, but what he sees is a hot mess.

RIGHT: For a date, pair jeans with funky, heeled booties, and substitute the bulky sweater for a silky blouse.

The Ultra-Feminine Look

LEFT: She feels youthful and fun, but he wonders if she shops at Gap Kids.

RIGHT: Compromise by keeping that feminine feel in a more streamlined style. When worn wrong, puffs and peplums can be a woman’s worst enemy.

For The Love of Color

LEFT: In head-to-toe, girly color, she’s going for a polished look. He, on the other hand, sees a bottle of Pepto-Bismol.

RIGHT: Instead, use a neutral piece to tone down a more colorful item. Thus, she draws attention to her curves, rather than her clothes.

When Showing Some Skin

LEFT: She’s sure to get attention in this little number, but what he sees is a one-hit wonder.

RIGHT:Keep in mind that it’s always one or the other – cleavage or thighs – but never both.

With Makeup, Less Is More

LEFT: He wants to see you, not your bronzer, shadow, and gloss. 

RIGHT: The goal of products is to enhance, but not to mask.  If you see the product, then the purpose has been defeated.

So, DD, now you know that any trend can make a man’s jaw drop. When getting back into the dating scene, a woman’s style can work for her, across a range of looks. And let’s not forget that guys can sniff out desperation. The biggest turnoff for men – more so than any ol’ outfit – is insecurity.

Until Next Time,

Toni

Written for DFW Style Daily