I’ve always envied people who get dressed with ease. What a peaceful existence it must be to throw something on and leave the house with nothing but a cursory glance in the mirror. It could never be me. 

Despite over a decade working in fashion, the simple act of pulling together an outfit I feel confident, comfortable and authentically myself in – the holy trifecta of feelings we all hope our outfits can evoke – can sometimes be an arduous task. On my worst days, it results in mountains of clothes, anxiety spirals and multiple frantic texts to friends (“What’s the vibe though?? Is this too dressy???”). 

As someone prone to getting dressed-related meltdowns, I’ve always been intrigued by fashion hacks. Growing up, the first and most notable one I encountered was Cher’s iconic digital wardrobe software in Clueless. In the opening scene we see Cher scrolling through various items in her wardrobe, before landing on an outfit she’s happy with. I think many of us would find getting dressed much easier if we were able to use technology like this to see everything we already own (and come up with outfit ideas) at the touch of a button. 

Our wardrobes are often so stuffed full that we forget what gems we have in there and instead fall back on tried and tested pieces. While we all love our old faithfuls – for me that’s tailored pants, striped shirts, chunky knits and bomber jackets – not being able to easily locate and review what we own is a surefire way to feel like our wardrobes have much less in them than they actually do.

So when I first saw someone on TikTok extolling the virtues of using your iPhone’s Notes app as a DIY version of Cher’s closet technology, I was immediately taken with the idea. 

The premise is pretty simple. You take photos of all your favourite outfits (the ones you feel confident, comfortable and authentically yourself in), hold down on the photo, press copy and then paste the cut out of you in your outfit into your Notes app. The result is a catalogue of your favourite looks, something I’ve found incredibly useful when I’m feeling frazzled and time-poor. 

It also helps you deepen your understanding of your sense of style and what you’re drawn to clothes-wise. I tried it myself, and the experience piqued my interest in other ways we can ‘hack’ or ‘gamify’ our wardrobes. 

As a fashion editor, over the years I’ve written about and commissioned articles on a whole host of wardrobe hacks – clothes sandwiching, using a spreadsheet to plan what new items you bring into your wardrobe, TikTok’s three-word method – but my attention was well and truly grabbed when a friend of mine told me about her flatmate Hannah’s unique approach to curating outfits. 

The unexpected joy of randomly generated outfits

Hannah is a 33-year-old library assistant based in Auckland who, like me, has found the getting dressed process challenging at times. “I've never been very good at fashion. I've always been more interested in finding one item I really like and wearing it to death, which I did for many years,” she says.

Despite her fixation on her favourite items, she still managed to acquire a large wardrobe full of items she hardly ever wore. It was during New Zealand’s quarantine – a time we were all lacking in outfit inspiration – that she came up with her unique system. “I regressed into a teenage state where all I wore was hoodies and jeans, which is a great look but not very exciting. I wanted a way to get out of this rut.” 

While trapped inside, she was playing the Sims computer game frequently, and its ‘generate random outfit’ mode got her thinking. “I thought that would be such a good way to 'shop your closet' and put things together in ways I hadn't considered. I was also inspired by Cher's outfit generator from Clueless,” she shares.

So how does her system work? Firstly, you’ll need to create a Google Sheet – this is where you’ll log everything you own. 

“Name the first sheet something like 'tops'. Go through your wardrobe and try on every top you have. Every one. This is a great way to get rid of some excess clothes. If you don't like it, donate it. Does it need mending? Fix it. Does it need tailoring? Take it to the tailor,” she explains. 

Next, note down each item in a separate cell on the sheet e.g. 'Linkin Park hoodie' or 'giant blue button-up'. You repeat this for bottoms, coats, dresses, jackets and shoes; basically everything you own. “If you really want to get wild you can add sheets for jewellery, hairstyles, makeup – the only limit is your imagination,” she says.

Then you go to random.org which, according to Hannah, “generates random numbers using atmospheric noise, allegedly the most random of random generators”. Next, you set the numeric parameters for your first category (if you have 50 tops, your minimum would be one and your maximum would be 50) and hit generate. You repeat this for each category and you’ll have created your very own random outfit generator.

Hannah tells me this system has forever changed her approach to getting dressed. “I have become way more excited about getting dressed because I never know what the generator is going to spit out. I generate my outfits the night before in case something needs ironing or steaming, and then the next morning I don't have to worry about what I'm going to wear – the generator has it sorted.”

But she warns me there is a “terrible freedom” in not being responsible for your outfit. “If I look like shit, that's not on me, that's the generator. The generator has also put pieces together that I would never have thought of wearing in one outfit, and has been especially helpful in not only getting me out of my 'hoodie and jeans' rut but challenging my conceptions of what 'goes' together. There are no rules. What sounds wack on paper can actually be very fresh and cute when you wear it,” she says.

While there have been some outfit mishaps (her flatmate once told her she looked like “an insane Carrie Bradshaw” and she tells me many times it’s generated outfits that make her look like a kindergarten teacher on acid), the system has undoubtedly streamlined the getting dressed process. 

It’s also allowed her to think more critically about the items she owns. “If something comes up on the generator and you don't want to wear it, consider the reason. Is it not your style? Too big? Too small? A remnant from a past self that you no longer connect to?” she says. 

While handing over control of your outfits to a random generator might be some people’s worst nightmare, at the very least, the process can help you cull items you no longer wear and hone your sense of style by showing you the items you almost always want to wear. 

For Hannah, that’s button-up fitted cardigans, giant hoodies and T-shirts, and A-line skirts. And, as she says, “You might be surprised at what the generator throws at you”. After all, there’s nothing like a completely left-of-centre, randomly generated outfit to reinvigorate your relationship with getting dressed.