It’s a date!

The alternative guide to date-night dressing

Words: Rosie Goddard | Photography: Nick Gordon| Art direction and styling: Sabrina Scott

In the build up to Valentine’s Day, many a magazine article would have you believe that the success of a first date relies on the sultry outfit you choose to impress “him”, but let’s not get it twisted. This is 2016, and unless you’re Tindering it up, chances are you’ve already met/talked to/drunk texted/snapchatted/kissed the person joining you on said date, so there’s no point doing a 180 on your usual sense of style.

Tugging at bra straps, pulling up pants and refusing to sit down because you might split the sides of your dress add extra stress to an already awkward situation (what?! I was carrying some extra holiday weight). We say choose an outfit that makes you feel good and allows you to focus all your attention on your stellar conversation skills, not slurping your spaghetti and/or dribbling your drink.

Four Superbalist employees teamed up with Art Director Sabrina Scott to style their ideal date looks, and then we asked two sceptical staff members Danielle Theron and Max Lazarus to pass judgement. From comfy casual to all-white everything, these are the outfits they styled alongside their top tips to reaching the other side with the prospect of a second date, or, at the very least, a streamlined exit strategy for when things go awry.

'Daytime casual' by Dudu Ntoni

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The look: I like informality. Let’s not even call it a date, let’s just say it’s a “get some drinks and food” typa thing. My boyfriend used to be my friend and somehow we morphed into #LoveLivesHere without even having the conversation. So I’m all about taking a laidback approach with co-ords, slides, a bucket hat and bum bag!

The message: Comfort is king. Looking like I just rolled outta bed is EVERYTHING. I mean ALL the tingz!

The venue: This outfit is perfect for day drinking – let’s pop by Jamaica Me Crazy for some beers or picnic at a wine farm or even do a market. The shoes are great for walking and nothing is tight or restrictive.

Top tip: Gurl it is rough outchea! Just do you and when the right person comes along you'll know. But just do you all day.

What he said: “For a day vibe, I’m really into it. At night, it could look like I’m spending some quality time with my teenage son.”

What she said: “I like this. The shoes are amazing, and a bum bag is always an added bonus, although a tad casual for me. P.S. I wish I was fly enough to pull off a bucket hat.”

'Trim and tailored' by Talya Galasko

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The look: Cigarette trousers make me feel safe because they don't suffocate my thighs, but I've also been known to man repel quite effectively in a pair of loose-fitting pants. To compensate, a revealing top pairs best and this one shows me off in all the right places, i.e. collar bones, stomach, but not cleavage – let’s leave something to the imagination!

The message: Although the outfit seems to disguise it, it must be known from the first date that I am drawn to men's clothing. I've let him know with the high-waisted slacks that he will catch me in corduroy shorts at some stage. Otherwise, there's a very feminine side to me – what do they usually say, a lady in the streets, a freak in the bedroom? I'm probably a freak on the streets but also a lady sometimes. On the streets.

The venue: I love clichés and I am happy to go anywhere that allows an unadulterated consumption of 3-4 glasses of merlot, so it seems like a beach spot that turns into some sort of dance affair is best (I love to dance). Wait, are we talking about Caprice? I totally wasn’t going to say that!


Top tip: I'm a messy eater and drinker, so, yes, white perhaps isn't the wisest choice but there's nothing that a napkin tucked into a shirt can't fix. I'd recommend rigorous exercise before the date followed by one glass of wine (essential). Also look up the menu beforehand – there's nothing worse than ordering the paella and bursting into tears when little prawns arrive on your plate. (True story. I'm Jewish. Never had paella 'til I was 19).

What he said: “Mary J. Blige howarya! Seriously, this made me think of Mary J. Blige. This is a winner. I like the confidence. That top with the high cut is distracting me (in a good way). I never used to like high-waisted pants but I think I do now.”

What she said: “Jinne. Love the pants and mad respect for wearing all white on a date. How? I would be drenched in all of the spills within two seconds.”

'Beachy-ready boho' by Sabrina Scott

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The look: A first date is bloody stressful in itself so you don’t want to have to think about an outfit on top of everything else. That’s why a maxi dress is the best option as it’s so easy to wear with sandals and a sling bag.

The message: That this is 100% me. If you feel like you’re trying too hard and would never normally wear your chosen ensemble, then you’re doing it wrong.

The venue: The perfect venue for this kind of dress would be sundowners at the beach, a city rooftop or somewhere like Signal Hill. I’m not about that tight dress life and I’m probably going to be sitting cross legged on the ground which means a maxi is essential.

Advice: On a first date, you need as many distractions as possible so that you don’t have to focus too intensly on the conversation (nightmare). If it’s a sundowners situation, make sure you’ve got an array of different snacks, some cocktails and a sunset to stare at during a pause in conversation. Alcohol is the key here, ladies! You're not going to be able to survive this first date without it.

What he said: “For a casual beach date (or a trance party), I like it. But anywhere else I’d be thinking, “Is this a date or are we just churning butter as friends?”

What she said: “This dress is lovely, but I’m not about that boho life. Soz. Sundowners? Always a YES.”

'Boogie nights' by Dale Scogings

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The look: I’m a serious magpie so I love dressing like a disco ball – whether in shorts or party dress form. I think the black top balances out the bold shorts and the overall look is a fun, flirty alternative to your typical tight dress and stilettos. Plus, you can’t go wrong with a chunky heel!

The message: That I’m dressing for myself and a night out with friends rather than the guy. I love that it’s slightly OTT, but that’s for the evening, not him.

The venue: I don’t enjoy sit-down dinner dates so my ideal situation would be meeting up for a drink at the bar or club after some cocktails with the girls. Even better if it’s spontaneous or last minute as then I don’t have to put too much effort into over-thinking anything.

Top tip: Don’t get too experimental with your accessories. I once wore my favourite Unicorn Tears bag on a date and the guy couldn’t stop focusing on it, he kept asking me if it was a cooler bag, or, more specifically, “do you have a bottle of wine in there?” To make it worse, when we got up to leave, the chain got wedged in the table and I was stuck having to pry it out.

What he said: “Tell me about it, stud! Holy crap, Sandra Dee, you've got my attention. Oh man, I'm feeling some big-time hypothetical pressure to impress!”

What she said: "THOSE SHOES THOUGH!" 

'Cool, calm and collected' by Cayleigh Bright

The look: “Dress for yourself, not the person you’re seeing,” is solid first-date advice, but it's also a little irrelevant. Because if you live in Cape Town like I do, you’re actually dressing for yourself, the new date, your lovingly judgey best friends, the regulars of your favourite bar, that nice DJ whose name you can never remember, the ex you’re now friends with, your colleagues, your colleague’s friend who your best friend is kind of seeing, and your hairdresser, all of whom you’ll probably see if you walk up the road for a glass of wine after dinner – so you’d better like your look. In short, I chose this look because I like it. 

The message: Dates should be fun – this isn’t a job interview, and it shouldn’t feel like one for me or the guy I’m seeing. This blouse keeps it simple, while the mini skirt’s colour and pattern keep the look from being bland or boring.

The venue: I’m a big fan of dinner dates as first dates – if you can hold a conversation with each other, that’s a good start, and sitting in a quiet room at the movies or shouting over the music at a club isn’t going to show you that.

Top tip: Confidence goes a long way. Think of things that you like talking about ahead of time if you tend to get tongue-tied, and most importantly – I’ll repeat – this isn’t an interview or a competition. If the date’s making you feel uncomfortable, the good news is that you don’t even have to get your friend to fake that “Your house is burning down” call anymore – just open up a Whatsapp, say something to the effect of, “Oh no, a very important thing just came up!”, or better yet, “I’m done,” and get right out of there.

What he said: “Those sleeves are confusing me, they’re a little too Shakespearean for my liking but I’m sure other women will freak out over how ‘stunning’ they are. I like the skirt, though!”

What she said: “This is defs my fave. Super cute. Love the bell sleeves. I would probs wear something like this to a date, but just in all black.”