I Allowed My Boyfriend, Friends and Family to Dress Me for a Week

If you allowed anyone in your life to dress you the way they wanted to, what do you expect they would choose? That’s exactly the idea I put to the test with five different members of my friends, family and co-workers. When the idea first occurred to me that it would be interesting to know how different people in my life perceive my style, I was surprised. I’ve never been one to care much about what others thought of my choices because I’ve always had a strong opinion about what I’ve wanted to wear (I spent a year of my teens in a pair of comic strip–inspired tights).

However, once I got to thinking about it, there were endless questions I felt desperate to answer: How distinctive is my personal style if others can’t replicate it from the same pool of clothing? What does it say about the way I dress if they don’t put me in something that I would ordinarily choose? And, most worryingly of all, what if they’ve secretly been sticking their metaphorical noses up at my personal taste for all these years and no one dared to mention that I should pursue a new direction?

The hypothesis I landed on was simple: Firstly, that each person would dress me in a pointed way that they felt was within the parameters of my taste but also gave away their ideal version of me. Secondly, that it would be subtly obvious who had chosen what, and therefore indicate their relationship to me. I work in a creative industry, meaning casual dressing is part and parcel. So I decided to put it to the theory to the test and asked five of my nearest and dearest to style me each day for a working week.

In reality, the results were quite different. Not only were my perceptions of people’s preferences way off (they all dressed me much closer to what I like than I anticipated), but they also inspired me with some new wardrobe combinations. Sit back and scroll through the results.

My colleague
Anna Heaton Wearing Tiger Print Marks And Spencer Alexa Archive Dress


Tian Skene

Due to how much time we spend together week after week, admittedly this was my least surprising success. Not only did I instantly feel like myself in Tian’s choice, but it also gave me a fresh idea on how to style my favourite summer piece for winter.

My boyfriend
Anna Heaton Wears ASOS Yellow Jumpsuit and Air Max 95s


Asha Bhayani

Stereotyping slightly, I’d really expected my boyfriend, Craig, to put me in something feminine and slightly glossy, but instead what he chose was quite the opposite: a sporty tee layered under tomboy-ish dungarees. It’s a look that I’d actually see myself going for. His styling tip? “Wear with nice hair.” Always delivering wisdom.

My mum
Anna Heaton Wearing Yellow Knit And Polka Dot Dress


Tian Skene

I’d expected my mum to put me in a tailored trouser or something traditionally smarter. However, having both indulged in a lifetime obsession with polka dots, it wasn’t shocking she chose this dress. The pop of yellow was an interesting addition that was I may put on repeat.

My best friend
Anna Heaton Wearing Ganni and Zara


Craig Winterton

I was proud to feel instantly like me when I put this outfit on. An old favourite piece of mine, my bestie brought this pink leather jacket back from the dead (read: back of my closet) and paired it with my overworn slip skirt and trusty slogan T-shirt.

My younger brother
Anna Heaton Wearing Gingham Top And Jeans


Suki Fraser

Finally, the outfit I was most unsure of, although, not because I didn’t like it aesthetically. I can see why he chose this playful layering (I was surprised that he navigated it so well), but it really showed me how feeling comfortable in your outfit can go a long way to improving your day. It did remind me I had these shoes, though, and for that, I’m eternally grateful.

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