How to wear a date night outfit to the office

Before my Mum gets excited, a disclaimer: I didn’t actually wear this on a date. 

Here’s my number one tip for making dating totally stress free: be so busy at work that you have to literally run to every one of your first dates directly from the office.  It’s fool proof – no time to faff about at home trying a new smoky eye, which immediately ends up going HORRIBLY WRONG so you have to take it all off at the last minute and just hope the redness caused by your speed scrubbing fades by the time you get to your rendezvous.  Or something.  A friend told me.  Cough.

ANYWAY, you guys, be it a date with a current squeeze, a potential squeeze, or a bestie fo’ lyfe – or even just a fancy dinner out solo in Wellington cos you deserve it godammit – it is possible to roll up in what you wore to work that day and still pass the CEO test while being dressed to impress.  


Step one is to wear something Aggressively Fancy.  In this case, it’s these metallic, rose gold, Instagram-approved, millennial-bait trousers from Topshop.  I need you to know two things:  they are surprisingly pleasantly stretchy, and there’s a matching blazer.  If my life involved any kind of fancy party activity, I’d be buying that blazer and wearing this with a sheer black silk shirt and some insanely high heels on the ASAP. 

Aggressive Fanciness is important because it takes the outfit up a notch, and prevents it from being a corporate snore fest.  Obviously, we live on a spectrum on fanciness, so your fancy might not be metallic trousers.  You do you – it’s important you feel good about how fancy you are.  

Next up, find something beautiful but modest to wear with your Aggressively Fancy Pants.   In this case, it’s this frigging ridiculously gorgeous blouse from Wilson Trollope.   It’s seriously good – please scroll to the verrrry bottom of this post for a closer look (I’ll wait right here).  It’s also a fabric that looks ace in candlelight (as do my pants) which is obviously A+ date material. The thing that makes it work here is that it’s long sleeved, high necked, and muted.   This outfit is all about finding the balance between “hey there, can you pass me that report on trends in financial literacy” and “hey there, can you pass me that Negroni”.

I went for these shoes because I’m obsessed with them at the moment due to their comfiness and hiiiiigh heel.  Also, they obviously also work really well to tie together the colours in my outfit.  The key is to remember that you have to wear these shoes for a very long day – from 8am to ???? (you do you, girl) – so do not wear anything that is slightly too tight, slightly too high, or slightly too fucking annoying.  Hobbling is not a great move on a first date.  Colour. Me. Surprised.

I also went for a statement earring, because I’m extra like that.  These are workplace optional, but great to chuck in your bag for a quick ritz up before you leave.  Key tip: on a date, you are usually only visible from the waist up, so (much like a newsreader) this is the bit that your audience sees.  Also, while you’re putting these on, it’s a great idea to check your teeth for spinach.  Yes, even if you haven’t eaten any this year.  Just check.

Now, you might be looking at this and thinking “I would never wear that on a date, no wonder that girl can’t get a man”.  Putting aside the unanswered question of my dating life, feel me when I give you this piece of A+ life advice:  Do Not Wear A Costume On A Date.

No.  Not a clown costume.  What I mean is: don’t put on someone else’s look for an evening.  If you are the girl who thinks sparkly pants are amazing, then just be that girl.  If you’re the woman who last wore high heels in 2002, then please, for the love of all that is holy, just show up in flats.  Do not eat seafood just because your date likes it, if you think it’s foul.  Don’t laugh at their jokes if, in fact, they are kind of nasty/racist/just not funny, okay.  There’s no point.  You aren’t going to change yourself permanently to suit someone else, so you may as well be yourself.  All the way down to your style (and the pants that you’re wearing).


Top is from Wilson Trollope - this fabric is also available in a dress. Pants were a straight-up impulse buy from Topshop.  Shoes are from The Iconic too long ago (sorry), but these are a more spendy and very nice option.  The earrings are from Lovisa, who have a website but no online store in NZ (IT IS 2017 COME ON).