Get thee a spreadsheet!
Round about this time last year, perhaps a little later, I was really, really fed up of my clothes. I didn't feel as though I liked the ones I had, and I felt as though I was wearing the same things all the time. I knew the first part of that was daft, because I'd loved the garments at first, so was boredom the true problem? As Jack Sparrow so rightly put it, the problem is not the problem, your attitude to the problem is the problem. And so I drew up a spreadsheet to see what I was actually wearing on a regular basis. All I did was boff in every morning what I was wearing. Top (or dress), bottom, legs, shoes, cardi/jumper, jewellery, shoes, bag, coat, perfume. You'll probably want different categories - I doubt as many people think as often about perfume as I do, and gents might want to look at their ties
It can be really easy to pick up the same things day-in, day-out, always to wear that cardigan with that dress, or that jacket with that shirt. The first thing the spreadsheet taught me was that I was actually wearing more things than I realised, but always in the same combinations. Tartan skirt, blue jumper. Long pink and grey skirt, grey longsleeved top, cranberry cardi. Once you know where your 'repeat offences' are, you can switch things round. Even if it's just the jewellery or tie, it can make a big difference.
When you've been keeping your spreadsheet a while, you can identify patterns, and that's really helpful for future purchases. I was surprised to realise the vintage items I use most often are practical, unflashy ones like my black day bag and tweed jacket. Cocktail frocks are all very well, but on a cost-per-use basis, that tweed jacket is my biggest bargain ever! As a result, instead of being lured by yet another lace dressy dress, I've bought another suit (because skirt AND jacket gives you lots of options), and been able to target my knitting so I'm making things that work in terms of colour and style with items I'm already wearing. I'm making far fewer impulse-driven bad vintage purchases, saving myself money and heartache. You might look at your spreadsheet and see you wear the same trouser and shirt combo all the time. Clearly you like it, but could you expand on it? Could a similar shirt give you more options with the trousers? Is there a jacket that would look great with both? This is why the spreadsheet is brilliant.
I don't have a massive amount of clothes, which is why you'll see me posting about wearing things I wore four years ago. In fact, today I'm wearing the same dress as I'm wearing in the photo at the top of the page. That photo was taken in 2012, and the dress was nowhere new then. Today, though, it's paired with a round, autumnal-coloured brooch, boxy 1960s bag and black wool bustle jacket. All hail the wardrobe-rejuvenating power of the spreadsheet!