Growing up, my dad had this weird thing about charity shop clothing. My mum was the total opposite, but she mostly looked in charity shops because she had a thing for collectors’ items – I don’t get it, but it was one of her many hobbies. I remember my mum coming home one time with a posh shirt – still in its wrapper – and having to persuade my dad that it was OK to wear.

I guess my dad’s attitude rubbed off onto me.

Until very recently, charity shop clothing wasn’t something I would wear. Part of that is because the men’s sections aren’t often great unless you want to buy jeans worn through at the crotch and knees, but to be honest I guess I was just making excuses.

In reality, it was probably a status thing. Surely, you have to be desperate to buy stuff from a charity shop. Right?

It turns out rich people buy from charity shops

Back in the heady days of 2014, I watched an Anne Robinson – you know, The Weakest Link – documentary called Britain’s Spending Habits. It was brilliant, but sadly isn’t on iPlayer. One of the many thrifty people Anne interviewed was one Baroness Jenkin of Kennington, who was quite fond of second-hand clothing.

Actually, she’s quite fond of saving money in general. There’s a good article, surprisingly by the Daily Mail, that’s worth a look.

That stuck with me, but I still didn’t really commit. I’ve read somewhere that it takes eight or nine touch points to sell you a product or idea, and this might only have been one.

Later on, I would read The Millionaire Next Door. You can read my review on this site if you’re interested. Anyway, “goodwill” (aka charity shop) clothing was mentioned briefly in that book as something that millionaires were quite happy to wear.

Oh dad, how wrong you were!

My first charity shop piece was bought for a stag do

One of my friends was getting married, and in top form he decreed that tweed jackets would be the theme of his stag do in London. We were to wear either a tweed or other gentleman’s sports jacket and hit the pubs.

As an aside, that night I learned that drunken Boris Bike riding is a terrible idea. Fortunately, only as a witness.

Anyway, I didn’t have a jacket that met this description. So, I did what anyone would do: hit the charity shops.

OK, I didn’t actually buy tweed. You’re at the mercy of what’s available. However, I got quite attached to the jacket I bought. Interestingly, the pattern has since come back into fashion!

My favourite jacket, bought from a charity shop
Bought from a charity shop in Lincoln for under £8 – lambswool – veteran of many parties.

Because I paid about £8 for it, that jacket got worn in situations where I just wouldn’t wear a £100 sports jacket. I’ve worn it to weddings with a pair of chinos, and to the office, but I’ve also worn it with jeans and a t-shirt out and about. In terms of value-for-money, it is the single best item of clothing I’ve ever owned.

Since the success of the first one, I’ve bought others

My second-favourite sports jacket is also 100% woollen. However, I had this one part-tailored to fit me, so it’s a bit pricier at £70 all in.

Yes, for £70 I have a tailored pure wool sports jacket. It looks badass.

My second-favourite jacket, also from a charity shop
Bit smarter, pure wool and part-tailored. Goes great with chinos or jeans.

This one is a bit pricier, so it usually gets worn to nice places. The first jacket is a social piece, but the second one comes to work more often.

I did briefly have an awesome linen jacket for a summer wedding, but it didn’t match the capsule wardrobe I’ve assembled, so sadly it was relegated back to charity. However, that one cost me about £20 and lasted for a couple of years. Not bad for smart casual clothing.

Good stuff for men to buy in charity shops

The pattern here is that my favourite charity shop buys have been smart casual/ semi-formal jackets.

Why? Think about it: most people don’t dress smartly all the time. They tend to buy something like this for smarter events, and probably only wear them a few times before they get bored of them or get fat.

Which means they’re not far off new.

This is great news for people like me, who would be afraid to damage something they’d spent over £100 on in today’s money, but are completely reckless in risking damage to something much cheaper. I don’t know what it is, but when there’s less investment in it, I tend to take more style and wear-and-tear risks, which in turn means I have more fun in cheaper stuff.

Life’s about fun, so charity shop stuff is a winner.

I also buy ties there. Obviously, since COVID, ties have basically dies out in the office – good riddance! However, for the odd occasion when ties are required, no-one will know if you’re wearing a tie that cost you £60 from John Lewis or £2 from Oxfam.

Trousers can be hit-or-miss. Occasionally there are some good chinos or jeans, but generally men wear their clothes to death, so I’ve not had much luck on the casual clothing front.

Coats can work. I’m pretty well provisioned on that front, but there have been some good coats in some of the shops I’ve been to.

Belts can be good. Lots of people outgrow perfectly decent belts, which means they’re in charity shops eventually.

Ladies have more luck in charity shops

Stereotype maybe, but women tend to cast off clothes with hardly any use in them. Or, well, decide that size 10 was a while ago.

Which Lady SierraWhiskyMike has exploited to maximum benefit.

Again, smart casual or semi-formal seems to be the winner. As well as a couple of nice leather jackets that look properly badass, she has found some great dresses and playsuits/ jumpsuits (I learned that ladies have made coveralls fashionable and appropriate for smarter occasions, which is smart thinking I wish would catch on in menswear).

There’s something awesome about not being marketed to

When you go to the high street to buy clothes, you’re just getting marketed to. The soft lighting, posters on the wall of hot-looking young people on a beach with a surfboard, all smiling or staring into the distance. Music deliberately chosen to fit the style of the brand.

Eurgh. You’re being psychologically attacked and all you wanted was to replace a holey t-shirt.

Obviously, charity shops don’t do that. They can’t really afford to, and they don’t choose their stock.

I really despise being marketed to. I don’t mind when it’s something I’m actually already going to do, I just hate sneaky tactics to try and change my mind. For example, if you’re going to buy a laptop and the guy upsells you to a higher spec, that’s OK. I am there to buy a laptop, the guy puts forward his argument, I agree and buy the better one, I leave happy – that’s good salesmanship.

But walking into a shop and being told “Hey, your wardrobe is inadequate. If you dressed like this instead, you too could be having salty sandy sexy beach parties! You might even look like you’re 25 again! BUY THIS OUTFIT!!!” – not cool. That can’t be a healthy way to live.

Buying clothing from charity shops pleases me. It’s like giving the finger to over-the-top consumerism and being a dick to marketers.

Final thought

If it’s good enough for millionaires, it’s good enough for me.

I try to buy most semi-formal or smart casual stuff from charity shops first, now. I reckon my woollen jackets will last a long time, which is awesome, but when they wear out I know what I’ll try first.

I’ll keep trying to get work clothing from charity shops, too – I have a desk job, I basically sit and do theoretical stuff with brief moments of talking, it’s not like I’m out having fun and dressing to impress. Makes sense to keep costs down.

I love my parents, but it’s telling that the one I’ve gotten into investing in their own pension is the one who embraced charity shops. Well done mum, have a gold star! Meanwhile, I can’t get my dad to take his retirement planning seriously.

This is where it ties into financial independence

Yes, it’s cheaper to buy second-hand clothing. Obviously. However, the deeper connection is psychological: if you’re going to optimise your life so that you can retire early, being willing to break social conditioning is going to be key. There should be no automated, programmed behaviours that go unquestioned. You should consider other ways of doing things. Simply upping your pension contributions will obviously help you retire earlier, but why not have a look at what else you could optimise?

Bit of a philosophical twist for a money blog, but at a certain level this stuff starts to creep in. You can’t really talk about habits and spending without looking a bit beneath the surface. Anyway, I hope you found this useful and maybe it will inspire you to try out charity shopping if you’re not already doing it and save a few pennies for investments.