Francesca Dattilo, MSW
Certified Law of Attraction Coach
Certified Style Coach (MIASC Accred.)

Call me:  613.204.0781


  • By Francesca Dattilo
  • 18 Jan, 2017

I have a few single friends who are looking for love and are dating.   Given, I am a Style Coach (tm) they will ask me what they should wear on a date.   I have one friend who spent many years dressing in a masculine way and was disconnected from her feminine side.   She spent so much time being one of the “boys” , they stopped seeing her as a woman.   And face it, most heterosexual men want their women to look like women!

After spending some time with me, she has revamped her wardrobe to reflect a softer side of herself.   She now wears skirts, blouses and heels. Although, she still wears her jeans and t-shirts, her jeans are now more fitted and tailored and her t-shirts are of finer materials, have interesting details and pretty necklines.   She is feeling much more confident and men are showing more interest.

Even though what we wear does not encompass all of who we are, our personal style is our personal brand and does affect how others view us and who we attract.   I recall in my mid 30s, I went on a date and my date showed up wearing a t-shirt and sweat pants with his hair slightly disheveled.   He was a nice enough guy, but I just could not get past the fact that he did not make the effort to put his best foot forward in how he presented himself.   I thought “This is probably how he dresses each day.”   He did not demonstrate to me that he had pride in himself.   I never saw him again.  

So here are some tips for dressing on dates and in particular a first date:

  • Be comfortable.  Make sure your clothes fit, not to tight and not too loose.  When your clothes don’t fit you properly, it is hard to be comfortable or confident. If you are having difficulty breathing in your clothing and pulling or tugging on your clothing, you will appear nervous.  If you are drowning in your clothes, you will appear sloppy.  

  • Dress to suit the environment of the date.  If you are going to play mini-put, don’t wear your stilettos! Opt for a comfortable and stylish flat.  You can still look cute wearing a patterned or striped sun dress, denim jacket and a white pair of sneakers or a pair of flats. And, If you are going on a super- active date, definitely leave the heels at home.

  • Wear fresh, clean, pressed clothing.   Please don’t take that pair of jeans or that shirt out of the laundry hamper to wear for your date. Men, if you are going to wear a sports shirt or dress shirt, iron it.   A wrinkled shirt conveys the message that you don’t care.

  • Show off your best asset. If you want to look sexy, but not sleazy, limit the amount of bare skin.   For example, if you opt for a short skirt because you have great legs, don’t wear a low cut top.   Conversely, if you like your cleavage, show it off, but opt for a skirt that hits you just above, at or below the knee.

  • Dress more casual if the date is during the day.  Amp up and go more formal in the evening.  Daytime looks can include a Romper and Sandals or a striped tank and a black jean skirt with flats or 2” booties. Night time looks can include a faux leather pencil skirt with a silk tank top or a little black dress with colourful heels. 

This is not an exhaustive list, but it is a good start.  Even though you want to make the best impression possible on a first date it is most important that you be yourself and that this is reflected in your style.  

If you are wanting to have a style that reflects your individual personality so you can attract the love of your life I invite you to contact me .

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