At this point in my life I’ve had enough first dates to open a dedicated research facility into them. Some have been awful. Some have been good.
A couple have turned into something more. One thing they have all had in common? I spend entirely too much time worrying about what to wear on them.
Epic wardrobe malfunctions. Panicked bouts of last-minute ironing.
Oh, and that one time I changed my entire outfit in the toilets of a pub after downing a pint all over myself two minutes before she rocked up.
My friend Vijay still mocks me about the time I called him absolutely distraught before going on a first date with a fashion editor. I was paralysed in front of my wardrobe wearing nothing but my underwear and a pile of rejected shirt options. I genuinely believed that my entire romantic future depended on me picking the grey jumper over the navy one. “Oi mate,” he said wearily, “it’s not bloody Vogue Week.
Just wear something clean that fits.” He was bloody right too. She later told me she couldn’t even remember what I’d worn – apparently my life story of bread-making had been far more memorable. There exists a chasm between what we British men think we should wear on dates and what actually makes a good impression.
We’ve all fallen foul of internalised ideas about “making an effort” that often translate into us looking like slightly miserable versions of our usual selves. I’ve seen grown men who, under normal circumstances, exclusively wear jeans and t-shirts turn up in stiflingly straight chinos and button-ups that are probably still displaying their shop creases because Mum dressed them so well. Dark jeans, visibly less lived-in than their everyday counterparts.
Shirt, either plain Oxford or faintly patterned. Desert boots you keep at the back of your wardrobe specifically for “smart-casual occasions”. Guys, I’m looking at you.
It’s comfy, it’s flattering, it’s not gonna shock anyone. But it also screams “I made absolutely no effort to be myself”. The thing is, no women I’ve ever spoken to care about this uniform.
Instead, what they repeatedly told me they actually wanted to see was a man who looked like him. Him, but just slightly tidied-up. “I want to see what he actually wears day-to-day,” said one friend, “not what he thinks he needs to wear to pass some stupid velvet rope blocking him from Relationship Land.” Another: “When he walks through the door and I can see he’s made an effort, sure. But if he looks like his mum dressed him for his school photo, I know I’m gonna be bored stiff by him.” The best dates I’ve ever had, where I felt most “myself”, were when I wore clothes that I would normally wear on a night out with friends, but just with extra care taken on the details.
Go for your favourite jacket that always gets you compliments rather than the new jacket you don’t know how to wear properly. Wear those battered boots you’ve had forever rather than those new ones that creak every time you take a step. Clothes that tell a story, instead of clothes that scream “please think I’m cool”.
You want the effort you put into your date outfit to go into things that matter. Like ensuring it actually fits you properly. Is ironed.
Suitable for the venue you’re meeting at. Not into fabric-weaving an entirely new version of yourself from scratch that you’ll never wear again. Because trust me, if she likes you on that first date she will eventually see what you normally wear to a club night.
Starting off as yourself just saves you the embarrassment of that reveal. It used to be my go-to uniform for any first date. One night I turned up to meet my date wearing it without realising, only to discover that she too was wearing black jeans, a black t-shirt and an equally worn leather jacket.
We were both too ashamed to admit exactly why we found that hilarious and instead spent the evening bantering about being in a freakishly goth-lite cover band. She still reminds me whenever we run into each other that she knew we’d click because “you didn’t dress like my grandfather on that date.” Here are the categories of biggest first date fashion crimes I’ve seen committed. Most of them by myself, obvs.
The Drastically Out Of Character One: When you ditch your signature look completely in favour of something you would never, under any normal circumstance wear. Guys who live exclusively in band tees and jeans showing up in button-ups, slim-fit chinos, and nice shoes, looking like your dad’s bizarre idea of what he thinks millennials wear these days. Asking themselves the whole date where the hell they put their beloved beanie collection.
The Tourist Test: Wear something new on a first date and something will ALWAYS go wrong. New clothes don’t know your body, your body doesn’t know new clothes. Shoes will pinch.
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Strange bulges form under fabric nobody’s worn yet. Shirt collar won’t quite lay how you want it to. I once wore brand-new shoes on a dinner date and spent the whole time tip-toeing around like Bambi on crutches because they kept squeaking loudly every time I took a step.
Good times. The Trend-Hop: That jacket that looks nice but you feel funky wearing because it’s only really been seen on celebrities in rap videos? The shiny new blouse you thought looked amazing but now suspect gives you shrub-face?
Save the fashion gambles for when you’ve already got them laughing at your jokes. One of my friends wore what he thought was a super trendy jacket on a casual pub date. By the end of the night he was so self-conscious about looking like he’d raided his dad’s wardrobe that he couldn’t relax – especially when his date rocked up wearing a comfy jumper and jeans like it was literally no big deal.
The Pocket Square/iPuff/Lapel Pin Aficionado: British men aren’t known for our mastery of accessories. Add “first date nerves” into the equation and suddenly we’re suddenly rifling through our closets for the novelty jumper sleeve or head-band that we never wear to adorn ourselves with. I once saw a mate wear a beret on a first date.
An ACTUAL BERET. If you don’t already wear said item as part of your normal look, step away from the dang accessories aisle. What tends to go down best, according to the many ladies I’ve bored with this entire topic: •Clothes that fit you.
Sounds simple but you’d be surprised how many men show up on dates wearing clothes that are either too big (why are your trousers covering half your shoe?! ), or so small you’re basically a walking muscle shirt. •Clean clothes that aren’t stained and where no buttons are hanging off by a thread. The girl who’s now my fiancee once told me she was partly won over on our first date by the fact that my shirt was ironed. “Not because I care about ironing,” she said. “But because it showed you’d made an effort without trying to be anyone else.” •Footwear suitable for the location of your date. There’s nothing more off-putting than watching a dude hobble about in clunky dress shoes during what’s supposed to be a romantic stroll through the park.
The horror I caused when I wore leather-soled shoes on a date that unknowingly required us to traverse through several patches of wet grass is not something I’ll ever live down. •One nice Conversation Starter – interesting socks? Unique watch? Jacket with history behind it?
Doesn’t have to be flashy or overtly noticeable but gives you both something to bond over. •Something appropriate for the activity you’re doing on the date. Fancy restaurant? Casual drinks?
Hiking up a mountain? You get where I’m going with this. On any given weeknight I’ll likely wear dark jeans, a shirt or knit depending on where we’re going and what the weather’s like, and then probably a jacket to top it all off.
That’s my general formula. Of course the specifics change but it allows me to pick an outfit that says “Brandon, but slightly less sleep-deprived” without veering too far off piste into La Suitcase Family Van territory. Hands down the most compliments I’ve ever received haven’t been when I went TOO far out of my comfort zone with what I wore.
But when I wore something that actually meant something to me, whether that was a jacket I picked up abroad during one of my travels, the scarf my grandma knitted me (yes, you read that correctly. It’s a good scarf and she knitted me many others. Buy your mum some knitting stuff for Christmas, trust me) or even just a band shirt that allowed us to bond over our similar music tastes.
Look, if you’re not dating Sally Magnusson or Vogue’s Head Of Ceremonials you’re date isn’t judging you solely on your outfit.
They’re judging you on your entire presence. outfit is just a piece of that puzzle. Wear something that fits you well and that you feel confident/confiding in (literally and figuratively).
Something you don’t have to worry about throughout the date. Then go out there and get judged on your conversation skills instead. Bonus note: London dates versus the rest of the UK dates.
Truth is, what’s considered “smart-casual” in London is not the same as what’s considered “smart-casual” in Bournemouth. Knowing your region’s slight dating attire inclinations shows a level of awareness that is infinitely more attractive than the shirt you’re wearing. A few years back I went on a first date in Edinburgh.
I vastly overestimated how smart you need to be. I showed up to (what was, unknown to me) a SUPER casual pub looking peak business casual. Proper trousers, button up shirt, loafers.
The girl looked at me and said “Oh my god, are you giving a presentation later?” Cue me spending 15 minutes in the toilet halfway through the date divesting myself of tie and jacket to stop looking like I mistook our drinksy catch-up for a quarterly sales meeting.
