What not to wear on a first date

Once you reach your 40s, there are things that you think that you will never need to go through again.  O-week boozing at the start of each new university year, the 90s spiral perm and the MC hammer pant  (although regrettably that bad boy stormed back into the fashion arena recently)

hammer pants

Another conundrum that you thought you might never deal with again was the first date fashion quandary.

First date preparation last time I was seriously single involved some Aapri facial scrub, a crimper, a spray of Impulse and out the door, with the echo of my mother asking if I needed a cardigan (she wasn’t there, but that echo had hung around since I was an 18 year old)

Dressing for a first date today should be simple, but just like the 80s, there are some classic outfits to avoid (and at least this time we know).  As always, we can take guidance from celebrity-dom when it comes to fashion faux-pas that you MUST AVOID ON A FIRST DATE.

Anything that suggests you are pregnant, have been pregnant or want to be pregnant.


Whilst something with a relaxed waistline is perfect for Aunty Lynn’s birthday party at the all-you-can-eat buffet restaurant, the first date is not the place to cause your new love interest to ponder what exactly is going on with your waistline.  Its unlikely that you would be foolish enough to try to pull off Cate Blanchett’s structural statement on a first date but let me warn you that in men’s eyes the babydoll dress is equally culpable in that IT DOES YOU NO FAVOURS.

Pregnant Kim Kardashian, wearing a nude baby doll dress, arrives at the Trump Soho Hotel in New York City

 Don’t over-theme

I think we’ve all been out on one of those nights where there’s a pivotal moment during the evening where you make a choice between quietly heading  home with your dignity intact or flinging your head back at the bar for another Tequila shot.  That same moment exists as the decision point in between throwing a little accent into your outfit for a lark, and OVER-THEMING.

A leopard print scarf or a pair of statement fringed boots? Yes.  Doing a head to toe theme?

dont' over theme


overly themed

One hundred times no.

 Beware of textures

 There’s a sensuality in texture, whether it is luxurious pile under bare feet or the silky smoothness of a 4-figure Egyptian cotton threadcount pillow against a flushed cheek.

What you don’t want is an outfit with so much texture that complete strangers are compelled to come up and stroke you.  This is unnerving for both yourself and your date.

kylie rug

Equally key is the fact that every layer of animal-like hair adds 5kg to your frame, and instantly ups your BMI if your date is once of those statistically minded folk.


I’m crying my eyes out over my coveted Stuart Weitzman wedges as I write this, but apparently, and most inexplicably, men don’t like wedges.  If push comes to shove, I’ll remain Single in my Stuart W’s and never feel compromised, but I do feel compelled to pass this onto you.

In your mind you have the utopian combination of a stiletto but with comfort, whimsy with  wearability, but APPARENTLY the first word that comes into his mind?


wedges hooves

I don’t want to stifle your fashion style and there is something to be said for fashion as a trigger for conversation on a first date, so feel free to take my observations with a grain of salt.  But if nothing else, there is a universal rule that I IMPLORE YOU to observe, that I guarantee will never lead you astray.


always wear pants

1 thought on “What not to wear on a first date

  1. Pingback: Meeting the parents – second time round | navigatingdating

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