Dolly Alderton | Contributing Writer | Friday, 12 June 2015

Fashion Mistakes We\'ve All Made On First Dates

Fashion Mistakes We've All Made On First Dates

The Debrief: As if date number one couldn't be any more nerve-wracking, you now have NOTHING to wear to it

First dates are stressful; I won’t have anyone say otherwise. It’s not like the adverts that depict women joyfully putting on a bit of lipstick and marching out the house to be greeted by a friendly, handsome man in a bar with low lighting.  It’s an experience ripe for disaster: one kiss on the cheek or two? The relaxed, continental dining style of sharing plates, or just your own meals? How many negronis until you get all shouty and sloppy? And oh what to wear, what to wear WHAT TO WEAR? 

There will never be enough time to get ready for a date. Even if you leave three hours (hour for ablutions, hair and makeup, hour for choosing an outfit, an hour to change the outfit) you will still run out of time. You will never think you look perfect enough for a drink with someone who could be your perfect partner. Here are the classic fashion mistakes that everyone has made on dates: 

Matching underwear 

It is a truth universally acknowledged that if you prepare for something; it will not come. No one will drop by when your house is clean, you’ll never bump into your ex after you’ve had your hair done, you’ll never have a successful date if you wear your best matching underwear. You will only go home with a man if you’re wearing your functional grey M&S pants from a pack of three and your sports bra. 

So tried and tested is this method that I once hear a story of a woman who used to go out on dates wearing disgusting underwear (thereby not tempting fate so the date would be a roaring success) and then keep a gorgeous underwear set in her handbag to change into before she went home with the guy. Cheating fate, if you will. Tricking destiny. However, this all went wrong when she went to get her card from her purse and the pair of wispy Myla French knickers tumbled out onto the table. Worse than being someone who wears grey pants, she was now someone who carries round a spare pair of pants. She actually sabotaged her own date by trying to trick the gods – it’s literally (sort of literally) the plot of a Greek tragedy. 

So, learn from this, take my advice on the underwear thing for a date: just wear rubbish underwear. If you don’t build it; he will come. 


Or crop tops or lycra or a very tight pencil skirt – we’ve ALL been the person who, in a frenzy of self-hate and panic – thinks the way to make a man like us on a first date is to dress like a mix of Joan Holloway and one of the Spice Girls in the Say You’ll Be There video. 

'Vixen,' 'Siren' all these words women are described as in books and films but rarely in real life as no one has the time or patience or malfunctioning sweat glands to wear a dress made entirely of leather. But the wave of pre-date panic makes us believe we will only be desirable to a man if we completely change our personality and become the sort of femme fatale who wears black lipstick only drinks whisky and says things like: 'hey, stud.' 

Being uncomfortable is not sexy. It’s very obvious when a woman is revealing more flesh than she’d like to, tugging down her skirt or putting her handbag in front of her bare midriff.  And it’s really not fun to spend the night breathing in so you don’t pop out of your dress, taking small sips of vodka tonic and counting down the minutes until you can get home and unleash your stifled fat and flesh and organs out of its bodycon casing like the jubilant moment they Freed Willy into the sea. 

My housemate has pre-date rule: put on your outfit and do something first. Take a ten minute walk or go to the shops to buy milk – if you feel comfortable, wear it. If not, change. 

The plain Jane vest 

The opposite of the above mistake – this is the option women take when they’re worried about scaring a man off with their sartorial choices. 

The Victorian blouse? No, no, too prissy. The 70s jumpsuit? He won’t get it. The ethereal white lace maxi dress? FORGET IT. 

So, instead, you plump for the least offensive item of clothing you have – a plain vest or a boring t shirt with boring jeans – in hopes that he won’t find it 'a bit much.' Then you get to the date, immediately don’t feel like yourself and want to go home and put on that kick-ass vintage blue suede mini skirt and start again. Instead, you sit quietly nodding while looking like a frazzled Wandsworth mum who’s out on the school run and didn’t have time to think about her outfit. 

Never again will your unconscious oppressing by the patriarchy make you compromise your truest, bluest sueded, wildest and most unapologetic self. Never. Again.  

Makeup reapplication 

The notion that you can change your entire face before a special event is something that is hard to shake off. Kardashian shading and lip-plumping a go-g0, there will always be a tiny glimmer of hope that tonight is the night you get your makeup so bang on that you’ll suddenly have very high cheekbones or more almondy eyes or a narrower nose. 

Not only will this NEVER HAPPEN but it also screw yourself for the whole date as the upkeep of this full face of slap is exhausting. You’ll routinely fear you have lipstick on your teeth or chin or that a fake eyelash is going AWOL. Constant makeup reapplication ruins a date – it makes you feel on edge and it also makes you absent. 

I’ve said it before, I’ll say it again: don’t go full-face for a first date. If he doesn’t fancy you, he doesn’t fancy you. An extra stroke of shimmer powder along your nose ain’t going to change that. If he doesn’t fancy you – more fool him. There’s someone out there who digs your fresh face and a blue suede miniskirt. And what a perfect first date that will be. 

Liked this? You may also be interested in:

How To Escape A Date You No Longer Want To Be On

Single? Why You Should Move To Manchester (Or Just Get Out Of London)

The Many Complications Of Setting Up Your Friends

Follow Dolly on Twitter: @dollyalderton



Tags: Dating