So, you’ve started chatting online because where else does anybody meet anybody these days… you’ve arranged a time and a place to meet and assess whether the WhatsApp banter translates into real life lols or is an awkward flop… and you’re hoping they don’t pull the ‘not letting you know they can’t make it and texting a pathetic apology 3 days later‘ trick. Then along comes the dilemma of deciding what to wear. You want to feel like yourself, but your best self, whilst feeling comfortable in yourself, and not the OTT version of yourself. Preferably not ludicrously overdressed and like you think a cosy pub is the place to show off your ballgown, or underdressed like you only remember about your Sunday afternoon date on the way home from the supermarket and had to run out in your leggings and old jumper. ‘Tis a difficult balance to strike! However, I’ve been on a few dates over the last few months and would like to think I’ve found a few confidence boosting outfits. Let me know if you agree!
Goes without saying that these are just my personal preferences and I’m by no means saying this is what you ‘should’ wear, but hopefully you know me well enough to know that 🙂
The trusty jumper dress and ALWAYS a good idea over knee boots
Is there an occasion jumper dresses don’t work for? Short of a red carpet, I think not. Super comfy, super feminine, super flattering, and ‘how could I possibly be overdressed I’m literally wearing a jumper’ kind of chilled. Over the knee boots make it that little bit more ‘date-ish’, and let’s face it, who doesn’t love a good pair of thigh highs? I bloody do. I never wear heels on a first date so flat OTK boots are my personal fave. A lil’ bit sexy but not in your face about it, yes please.
I want a relationship that’s as compatible as long boots and jumper dresses tbh. Setting the bar right there.
dress: Adrienne Vittadini at TK Maxx | boots: ASOS
The Daytime Date Darling Denim Dress
Denim for daytime? Groundbreaking. Jeans would be the obvious choice but I think a denim dress just feels that lil’ bit more fun. This particular one is from M&S yonks ago and I love how it nips in nicely at the waist without a belt to get on my nerves. Obviously in summer this would be cute with bare legs and converse or something, but ain’t no way I’m getting my shins out for the lads in this weather. Trusty 100 deniers it is.
dress: Marks and Spencers (old) | boots: EGO | jacket: H&M
‘Jeans and a Nice Top’s slightly cooler twin
Because if you’re not wearing jeans and a nice top, did you even go out?!? Here I present version 2.0: Shiny Pants and a Nice Top. V v simple but swapping jeans for faux leather trousers makes it that little bit jazzier without going the whole hog on vinyl trousers that are kicking around everywhere lately but look way too squeaky for my liking. Also, purple pants surprisingly go with everything. Would highly recommend introducing a pair of purple pants to your life, just FYI.
NB: Please kindly ignore the messy bun becoming progressively messier as I changed outfits. Rest assured I would actually brush my hair and don’t regularly go for the dragged-through-a-hedge-backwards look for a first date (not intentionally, anyway).
Slinky jumper, slinky boots
Now I’m all for super casual coffee dates, but sometimes a few drinks at night doesn’t hurt either. I’m all for getting out and about up a hill in my walking boots and anorak too, but y’know prefer not wandering off into the middle of nowhere with a complete stranger the first time I meet them. What sounds like a really cute idea suddenly seems hella creepy when you remember they could be anyone and you should probably stay somewhere very public first. Anyway, I digress. Back to the clothes. The over knee boots are out again! Honestly they’re just the absolute best and I can’t get enough. Same goes for the skinny polonecks – they’re kinda *elegant* (or as elegant as a klutz like me is gonna get, anyway) but also simple and minimal and don’t look like you tried too hard. We’ve already established by now that purple faux leather is a godsend, so here we have it in skirt form; when you find a good thing you go to town on it. Or y’know, go to town in it. Either way.
Skirt: Matalan | jumper: Primark | boots: ASOS
Disclaimer: none of said dates have gone further than a second meet so I’d probably ignore my advice if I were you.
Lily Kate x
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Max18th January 2018 at 3:35 pm
Okay thanks and noted! Ha ha! Why do I find your “disclaimer” so funny? I have no first dates planned, but I often need to find something to wear when meeting new people or going to the ballet. I am definitely going to look into some sweater dresses and the like. Shiny purple trousers, you say?