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I Let My Boy BFF Dress Me For Dates & This Is What Happened

by Laurence-Emmanuelle Bédard Published on May 12, 2015

The stress of finding an outfit to wear on dates is on of the reasons why I don't like dating. That and the fact that no one is asking, but that's another story. So I gave my boy BFF the challenge of dressing me for five dates. It seemed a logical thing to do, he's a guy so he would know what guys find attractive right? Here's how it went down...

I have to give credit where it's due, my friend Tolu can put together a good outfit, for himself anyway. I mean he shops in COS, can pull off a good suit and rocks the whole casual cool kid look pretty well too.

​Which is why I thought it would be interesting to get him to pick out outfits for five different dates. Outfits that he genuinely thinks would make a good impression on those dates.

The five dating scenarios I chose were: drinks after work, watching a band play, cinema date, fancy dinner and movie night at my date's house. I will leave you to be the judge on how he did. However before we got onto that part, here are a few one liners from Tolu, that I have to share with you. Boy logic is so questionable.

  • "Don't wear too much lipstick, it's only going to come off."

  • "These shorts/dress things (he means jumpsuits) are good, because it comes off in one go."

  • "Do you have diamonds? I thought every girl had diamonds."

  • "You don't need a big bag, just something to fit condoms and lipstick."

  • "Why do girls wear crotch bags?"

​He meant clutch bags...

Outfit 1: First Date, Drinks After Work

Shirt Dress: ASOS
Jumper: H&M
Jacket: Primark
Necklace: NewLook
Shoes: Zara

Tolu's Verdict

"For this outfit I had to find something that worked for the whole day. I thought layers would be good because at least she can be warm, incase he's a pr*ck who doesn't give his coat to a lady. Layers are also a lot of hassle to take off, so it means she won't be doing anything naughty."

My Verdict

So if the question is, would I wear this on a first date, the answer would be no. But would I wear this outfit, yes I would. I just thought you had to be a little sexy on a first date. But hey, what do I know.

Outfit 2: Watching A Band

Shirt: Topshop
Shoes: Zara
Bag: Aldo
Sunglasses: ASOS

Tolu's Verdict

"It's the second date, which means he did well (it's unusual for Tolani to get to this point). So it means it's time to show some skin. I chose legs instead of boobs, because I am sure I heard a rule about that once. I think this looks really stylish and not too try hard, kind of like the cool girl every guy wants."

My Verdict

Although you can't see it, I am wearing shorts under this shirt; something I had to fight for. I do actually kind of like this outfit. I wouldn't have thought of wearing this to a date. It's fair to say Tolu was pleased with himself for this outfit, he said and I quote: "This is the best you have ever looked." I am sure I have looked better.

Outfit 3: Cinema Date

Jumpsuit: ASOS
Trainers: Adidas
Jacket: Primark
Necklace: Forever 21

Tolu's Verdict

"I have put her in Adidas trainers - can she look any cooler?! It's chilled out and she looks really comfortable. I added the pink coat for a girly touch. It's like I am wearing trainers, but look I have a pink coat on. It balances it out."

My Verdict

I think my face in the picture shows how I feel about this outfit. I have no more to say, just NO!

Outfit 4: Dinner Date

Jumpsuit: Zara
Bag: NewLook
Shoes: Zara

Tolu's Verdict

"I put her in a jumpsuit because it's different from a typical boring dress. Yes guys like dresses, but it's nice to know a girl can look good in something else. It's sexy and bold. I didn't put a jacket with this outfit, so her date can offer his. Also I think the bag is cool. It's see through so her date can see what's in it, which is why I made her pack a condom. It's a tease."

My Verdict

It hurts to admit this, but he actually nailed it. I had hoped he would fail at this,so I could tease him forever, but this is good, very good. He even accessorised perfectly.

Outfit 5: Movie Night At His

Jumpsuit: Jane Norman
Shoes: Dune
Bag: Primark
Jacket: Bershka

Tolu's Verdict

"This is the night where her date is going to get some. We all know what a movie night really means. The outfit is comfortable and relaxed, plus it looks like pyjamas, so he gets that she wants to stay round. Plus, I have added a rucksack to the look so she can pack spare clothes, to avoid the walk of shame."

My Verdict

For one, I honestly thought 'come round to watch movies', meant come round to watch movies. Oh I have been so naive. Back to the outfit: it's okay I guess. I feel pretty comfortable and I like how it's cute and doesn't look like I put too much effort into it.

What I Learnt

Apparently boys are not all about tight dresses with boobs out, who would have guessed. If I take anything from this, it's that guys really do like the "cool girl".

I also learnt that I hate men telling me what to wear, it took a lot for me to let him take control. I don't know how Kim does it. But I guess Tolu is no Kanye.

This article was written by Tolani Shoneye with help from Tolu. Tweet her @tolly_t and follow her on Instagram to see her actual style @tolly_t.

Tell Tolu what you think of this outfits. Tweet him @l0rdhbk

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by Laurence-Emmanuelle Bédard