Welcome to womanhood, Caitlyn Jenner! Great dress! Just don’t wear it again, yeah?

By the time you are trussed up to an acceptable level the thought of casually walking anywhere will be unthinkable. Besides, men will shout "Boooobs!" at you out of cars

(Ping Zhu)

As I clanked back from Westfield Stratford City hauling two Boots carrier bags full of dyes, varnishes and toxic-when-inhaled sprays which make me the natural beauty I am, the thought tiptoed across my mind: "I wonder if Caitlyn Jenner is tired of being a woman yet?" This isn't to make light of the decades the athlete-turned-reality-TV star spent unhappy as a man – more that I own that DVF leopard-print frock she "casually" threw on to go shopping in Manhattan. There would have been nothing "casual" about the process.

I mean, yes, you can shove it on with 40 denier opaque tights, if bare legs are a no-go. But it can look frumpy. And you're going for "care-free chic". Better go with bare legs. Which will need to be freshly waxed with an instant spray-on sun-shimmer leg tint. That's on aisle nine. Don't worry, Caitlyn, you'll work out where all this stuff is. You're going to be in Boots a lot. In fact, all the time.

The double bind being that one can never ever complain about it. Because one of the great tropes of the female sex is that we all just love "dressing up" – and that all those Saturday morning trails around department stores, buying things in order to make us satisfactory, are just like a Reese Witherspoon "I'm shopping!" montage in Legally Blonde.

Anyway, being realistic, what Caitlyn's DVF frock needs – as does the blue lace she wore to watch An American in Paris on Broadway, which I also almost bought – is a St Tropez spray tan, the evening before, then a leg oil to make the calves look glossy and sumptuous. Yes, the spray tan may leave a body imprint on your bed sheet like you had a one-night stand with a chimney sweep. Yes, you're going to go through a lot of sheets.

Oh, and don't think of wearing the DVF animal print with a comfy, practical ballet shoe. It needs a 120mm heel. But obviously – duh – don't leave the house without the ballet pumps, as you'll be immobile. You'll need an enormous handbag to hide the pumps. Do pit-stop shoe-changes in doorways.

A TV producer asked if I wanted a taxi to pick me up from home and ferry me to the studio the other day. "Better had," I said without thinking. "I'll be in the full fancy-dress Grace Dent clobber." By the time you are trussed up to an acceptable level, Caitlyn, the thought of casually walking anywhere will be unthinkable. Besides, men will shout "Boooobs!" at you out of cars and this will be – you'll realise – all your fault.

And most importantly, Caitlyn, now that you've worked out how to wear the DVF frock… don't even think of wearing it again. People will grizzle behind your back that they've seen it before. What's wrong with you? Have you only got one dress? Put it in the recycling! Find another frock, with its own set of tedious demands.

Famously, Karl Stefanovic, a news presenter on Australia's Channel Nine, wore the same blue suit every day on screen for 365 days to see if any viewer noticed. No one did. If Caitlyn Jenner wears that DVF dress again she'd be accused of cost-cutting, amnesia and slovenliness.

So I wondered – as I boarded the 97 bus, lugging a fresh supply of eyelash glue and Elnett – if Caitlyn ever thinks fondly back to how many more free hours she had in her previous life, when all that was expected of her was a blast of Sure and a sports jacket? Because now that she's established herself as a glamorous, well-put-together woman, she's a prime target for a voyeur pap-shot of her putting the bins out clad in a tracksuit and no lipstick. "Having a day off?" the gossip sites will then squawk.

I mulled all this over as I hugged my bag of ponytail bands, brow-definer, colour-repair conditioner and raspberry-scented dry shampoo for those days when a woman has "good", but nevertheless slightly oily hair, and washing it would strip it of all of its oomph.

When did I learn all this? Over decades I memorised the order in which the chemicals are applied and the minute but important differences between their effects. I learned the quickest way to go day-to-night as well as techniques that may take hours, but have the most alluring results. I learned a smoky eye technique that takes at least 42 minutes from first base to applying lashes. One wrong move and you're in Rocky Horror territory – but when it's done right, I am a sexy Kung Fu Panda leaving startled, love-struck mortals in my wake.

Or that's what it feels like, anyway. Heels, hot rollers and a good-fitting bra are a little like having a superpower. But with great power comes great – and often really quite boring – responsibility. The mid-appointment fringe trims, the upper-thigh hot-weather chub-rub pains, the knee exfoliations, the pre-sandal pedicures, the fight against grey, the war against dowdiness. If I were Caitlyn Jenner I'd be more than pleased with the woman I'd created – but sometimes, secretly, I'd really quite miss being Bruce.

@gracedent