What to wear for a first date after 40?

You would think that as we get older (and supposedly wiser) we would at least have this question somewhat figured out by now. Alas, “what to wear” remains one of our biggest—and most time consuming—hang-ups, especially in the face of dating.

Here are a few of my styling tips on meeting a man for the first time. 

Step One. First of all, remember that a man is looking for a woman. You need to look like a woman. I’m not joking. If you have very short hair (read boyish) or wear very baggy clothes, no make-up, carry a huge suitcase of a purse and wear flat shoes all the time, I’d like to suggest you re-think a few things.  I’m not trying to be unkind if this is you. But, frankly ladies, men want to see your feminine side. For example, soft, flowing hair is usually preferred by men—think of it as waving them a flag. (After all, men are not exactly masters of interpreting subtleties) Also, there’s nothing wrong with short hair as long as it’s feminine.  Try channeling Marilyn like my lovely model… we all know Ms. Monroe didn’t have any problems attracting the opposite sex!
Step Two. Take a good look at yourself in the mirror.  We are each our own worst critic.  “I’m too fat” you say. Well just stop right there! I’m a size 18 and I don’t have any trouble getting dates. So forget about your body for a second. Whatever you are looking at is what we have to work with. Get over it. Every woman, no matter what her size, thinks she is too fat somewhere.  It’s true!  Ask a skinny chick!

Step Three. What are your best features? Nice legs? Wear a skirt and heels even if it’s a little heel. Great décolletage? That’s easy—wear a ‘V’ neck top. (And yes, you can go a bit lower than you would wear to the office) ‘V’ necks are universally flattering as are crossover or wrap styles. These are your resources, so use what you’ve already got to your advantage. In the words of fashion’s Tim Gunn, “Make it work!”

from left: Midnight Cowl, Starburst Tee, Switch Tunic (all available at http://www.dianekennedy.ca/shop/ )

Step Four. Pick a pretty colour next to your face.  Most men like colours, bright colours.  Like red. (Again with the waving flag analogy) But of course pick something that looks good with your skin tone. However, if you must wear black, put it on the bottom. Remember you are trying to catch his attention, not disappear into the night! A little sparkle doesn’t hurt either.  Something that catches the light, like a pretty necklace (not sequins!!), will draw his attention and light up your face.  Remember that on your coffee or dinner date he will mostly see you from the waist up. Also, please ditch the suitcase and instead pick a smaller, sleeker purse. Large clunky bags send the wrong message, something like “I already have everything I need!”  Just trust me, scale it down.
While these tips do not guarantee that your date will work out, they should give you a bit of a confidence boost. Ahh that C word again… it’s probably the most important thing you can take away from this article. Men like confidence. Confidence is always in style. Wearing something pretty and looking feminine will help you find yours!

2 Comments (+add yours?)

  1. Sherry
    Aug 12, 2011 @ 18:33:34

    Fabulous! Thank you. 🙂


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