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How to Dress for Dating Success –

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How to Dress for Dating Success

A few weeks ago, I had the pleasure of working with a 40-something, attractive, independent, intelligent, hilarious, athletic woman. Maria* is a successful lawyer who owns her own condo in a hip Vancouver neighbourhood and enjoys traveling. She is also single and looking for love. After meeting a countless number of duds, Maria admitted she often felt indifferent going on dates with the men she met online. When she showed me what she typically wore, it was obvious to me her feelings about dating were coming through in her personal style. She looked to be uninspired, bored and disconnected. She needed help to learn how to dress for dating success.

The term “dress for success” is usually in reference to career success, but you can also apply it to dating.

I discussed with Maria how she could bring intention and a sense of occasion to her look. She already owned everything we needed to made it happen. Sometimes, it’s not what you wear, but how you wear it. First up, I searched through her accessories. I literally found some hidden gems in there! To soften her super-conservative look, I added a bold statement necklace that I found unworn in the back of a drawer. In order to help her appear more casual and approachable, I rolled up the sleeves on her blazer which had an instant effect. In addition, I half-tucked some of the blouses she usually wore fully tucked, which made her look more modern, cool and slightly undone. I also paired her all-black go-to outfit with a gorgeous pair of red flats to add some youthfulness and personality.

The Post-Closet Consult Follow Up

I checked in with Maria a few days ago. She told me how she’s been putting her work and her weekend outfits together more thoughtfully, and how doing so has shifted her attitude and outlook. Because she has been dressing in a more flirty way, Marie says she feels flirtatious. She finds herself in situations where attractive men are flirting with her…like the grocery store! As a result of her small adjustments, Maria is feeling more like herself…fun, optimistic and confident.

Tips to Dress for Dating Success 

Just as in business, think of your dating clothes as a non-verbal communication tool. Know your audience. Be aware of how you naturally come across (aloof? serious? jaded? insecure?) and adjust accordingly to strategically send out your desired message.

To dress for dating success is to dress with intention. Use your personal style to give clues about your personality to potential mates. Romantic, edgy, bold, adventurous, smart, friendly, self-assured, etc., can all be said with your clothing. You’re more likely to attract someone compatible because he or she will be able to read you better.

Dress to feel how you want to feel. This is key! If you want to feel lovable, attractive and cherished, then wear something that makes you feel that way.

Let your feminine side come through. Showing legs OR cleavage (please note, only one at a time) are an obvious way to do that. But a necklace that draws the eye up towards your kissable collar bone or dangly earrings framing your lovely face are also alluring in an understated way. The key is to look sexy, not easy.

Your Dating Success Pro 


A woman with long hair is standing in front of the camera.Nicole Haley

Nicole Haley is a Relationship Navigator at who runs dating workshops for groups of women as well as private sessions for individuals who want more in-depth romantic coaching. In a society where many women are fiercely independent, Haley helps women to tap into their feminine energy. “We are so used to existing in the masculine, that when it comes to connecting to our feminine energy, we tend to feel uncertain and uncomfortable. We misinterpret this femininity as weak and needy, rather than recognize its power, beauty and strength.”

Savvy in the City

Join us on Thursday November 3 for Savvy in the City  – A new kind of Ladies Night. It’ll be an evening of friendship, fashion and fun. Nicole will be joining The Joy of Style plus Ana V and Emily Roop to discuss simple changes you can make to your outfit, hair, makeup and mindset to transition from the office to happy hour.

Sip on some bubbles and enjoy some appies as we breathe new life into your wardrobe and help set you up for happily-ever-after.

Tickets are limited. Get yours today!

A woman standing in front of a wall with her hands on her hips.

Dee Clarke

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*name has been changed to protect the innocent.





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  • Reg
    February 14, 2018 at 10:39 pm

    Love how she didn’t have to get a whole new wardrobe! Bet you equipped her with tons of options with her existing wardrobe. You have great creativity!

    • Dee Clarke
      February 26, 2018 at 3:17 pm

      She had a ton of gorgeous clothes already but wasn’t putting outfits together in a way that gave the impression she wanted to give. My favourite part of the process is the closet remix. It IS fun to get creative with clothes and mix them in ways clients had not considered before.

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