English Rosiee’s Guide to First Date Fashion

Indian Prince Outfit
Simply dressing like an Indian Prince won’t always win you her heart 😉

As much as I idolise Carrie Bradshaw, my wardrobe is more Woolies than Versace and my shoes are more Mr Price than Manolo Blahnik. When you are earning Rands you need to make do as a no-name fashionista.

Anyway, what I am getting at here is that while I am no fashion expert, I do believe that what you wear is important and never more so than for single guys/gals trying to manoeuvre their way around the Cape Town dating scene. First impressions count, and much of that is decided by the clothes you wear. So here are my humble tips for guys looking to win the heart of a fair maiden…

Suited and Booted

Maybe it’s just the Londoner in me, but I love a man in a suit. Sadly, we don’t see enough of them in Cape Town where board shorts and flip flops seem to be the height of fashion. Dressing up gives the ladies the impression that a bloke has a high-powered position and cash to splash (many women do have a Christian Grey fantasy).

To highlight my point, I lived with a Goth dude at university and once told him the only way he would be allowed out in my world (of all things glittery and fabulous) would be if he wore a suit.  After a lame protest saying that the only suit he owned was one he’d purchased for his grandmother’s funeral, he eventually gave in to my demands. Let’s just say he’d never seen so many girls ready to drop their panties for him than in the club that night.

Shoes for Shorties

There is no doubt that being short is a major disadvantage for a man trying to win a girl’s affections (this is made worse if he spends the whole date making short jokes about himself).

However, there is only one thing that vertically-challenged men can do in such a situation and that is to embrace their disability. I mean if they can’t distract you with their wit and charm then they can at least be skillful enough to stand on a step or offer the girl a bar stool, so he can reduce the impact of the height issue.

If you ever find yourself crushing on some short elderly troll, I hope you have a friend like #zlotybaby who reminds you to check out his shoes. Remember, if there is one thing women are obsessed with its shoes. We notice good/bad shoes on our friends, on randoms and we’ll most definitely notice a man in HEELS. And wearing them will only serve to remind us of how short he really is.

Ethnic Attire

Don’t make assumptions. Just because a chick looks like chapatti, doesn’t mean she has any real inclination towards men from the Indian subcontinent.

I once went on a couple of dates with a lily white dude that decided that because of my ethnicity I would be truly impressed that he had embarked on a 200 hour yoga teacher training course (I’m the somewhat physically challenged girl who sits in child’s pose for the whole of class), then takes me out to an Indian restaurant (cos if I was actually Indian, I wouldn’t be getting enough curry at home) and the pièce de résistance – he turns up on Valentine’s Day dressed up as Aladdin (maybe in his warped mind, dressing like an Indian Prince was guaranteed to make any ‘Indian’ princess go weak at the knees).

Oh and if that wasn’t bad enough he teams his costume with trainers. As far as I concerned, trainers (or takkies as they call them here in SA) are for sport. Nothing else. Unless of course you are chav (a big part of me escaping the UK, so I don’t plan on dating any of them here), in which case they go rather well with a fake Adidas tracksuit.

So guys, I hope my no-name fashionista tips help you get laid. Now rinsers tell us in the comments on what you love/hate to see a potential lover wearing on a date.


  1. I like your post on first date fashion and creating a good first impression.

    I think it is important because it shows that you care for yourself and you made an effort to look good.

    I think you post focuses on what men should wear, I’d like to hear more about female fashion, for instance how feminine attire seems out of fashion and you rarely see women wearing dresses, and looking girly, most wear jeans and more masculine clothing.

    Personally I’m a bit old fashioned in that way and think a girl should embrace her femininity and wear floral dresses.

    Also, something could be said about summer vs winter fashion and dressing for the occasion, don’t wear a suit to the beach, but also don’t wear boardshorts to the theatre.

    Liked by 1 person

  2. Thanks for reading my post. Glad you liked it 🙂

    I’m a pretty girly girl so I am more than happy to wear dresses as long as my date takes me somewhere nice. But I agree I am part of a dying breed. I guess some of the feminist types might have a lot to say about those that make an effort to look pretty for guys, and say that we should use our wit and charm to impress them rather than our legs, boobs and pretty faces or whatever. But most of my clothes I buy because they make me happy, the guys taking me out just give me an excuse to dress up.

    As for winter, yup its much harder to dress pretty in winter when all most us want to do is curl up in our PJs with a hottie (man or hot water bottle) and watch DVDs in bed 😉


  3. Nice post. Left to me id love anything simple, my meaning of simple dressing doesn’t mean rags or anything so so so cheap. so far it makes her gorgeous and absolutely stunning. Anything that’ll make her look smart and presentable. And no heavy makeups.
    But personally a nice gown with nice shoes or some smart top with jeans with good shoes. 🙂


  4. I think if you like someone go for it! They could’ve wearing the ‘Emperors New Clothes’ or a t shirt in jeans. All is fair game and conversation and chemistry will outweigh the threads:)


  5. I think overdoing us the worst. It’s nice to know that a guy made a bit of an effort but if he’s trying to hard it’s easy to doubt his qualities. As in “he seems like a cool guy, but all this effort already, there MUST be something wrong with him”.

    High heels was something what my ex fiancé wore. Short guys should look at all these midgets loved by ladies and chill. It’s all about healthy self esteem.

    Liked by 1 person

    • Yeah….the heels thing is a sore point. I must keep reminding myself however good his banter is, there is no way a 50 something can grow a couple of inches over the weekend 😉


  6. I have recently lost my phone with a good camera, which is annoying… also because I saw some excellent examples of guys’ pants that are not sexy/attractive, and would definitely turn me off if a guy showed up on the first date with them. It goes both ways, I try to look nice for the date, dressing appropriately – board shorts and a t-shirt can be seasonally and activity appropriate – and expect the guy to do the same. It also speaks to how much confidence they have and how likely they are to click well with you!

    Liked by 1 person

  7. Oh yes, those pants definitely deserve a mention….butt crack is defo a turn off. I’m kinda glad you don’t have the photographic evidence to torment us with though 😉


  8. […] Although the three scenarios above all suck. It could be worse. Anyone who has any sort of meaningful (or not) interaction with the opposite sex risks getting hurt but at least by putting yourself out their you are increasing the odds of finding happily ever after. Even if worse comes to worse a Tinderella will probably still be able to land herself a last minute date with an ‘Indian’ Prince. […]


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