Ladies and gents, after five days, we've hit crisis point. It all started so well, but as I discovered today, the key to keeping my boyfriend interested in this whole challenge lies in not waking him up early in order to pick out the clothes.

Letting my boyfriend dress me only works if the outfit is picked the night before. Otherwise, I end up dressed like this...

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Now, my colleagues tell me I'm overreacting. In fact, one even said I looked nice, so perhaps I'm looking for drama where there is none (it wouldn't be the first time). The truth is my boyfriend's done so well at this challenge so far that I've been struggling to pick fault.

Until now. I can't help but think that teaming heavy, buckled boots with a delicate lace pencil skirt (£22 at River Island) is a serious sartorial error.

I'm dressed like a biker up to the knee, and a secretary above. I don't mind the skirt / vest / bolero combo at all. There's some canny colourblocking going on, and I'm quite impressed he picked something so detailed, because he tends to scoff at my more embellished / patterned items (you should have seen his face when he stumbled across a blouse from Celia Birtwell for Topshop).

Let's take a look at the detail on the knit, which is a very old Star by Julien Macdonald piece that I reckon I've had for a good 7 years or so, back when I was going through a predictable boho phase.

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It's pretty, a bit unusual and it's keeping me warm. But oh, how this outfit is crying out for the teal t-bar heels I looked wistfully at before I left the house, rather than my Frye Carmen boots, which are absolutely brilliant (and so comfortable) but usually reserved for slightly 'tougher' outfits.

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I guess I only have myself to blame. After complaining about cold feet for days on end, it make sense he would shut me up by putting me in boots. But while these boots probably would have worked with any of the other outfits he's put me in so far, I really don't think they work with this one.

I should have known I'd pay for yesterday's success!