How to find investment pieces on the High Street

I’m a fashion expert – here’s the changing room tricks to try to make sure you find the best quality high street buys and don’t waste your money

  • Anna Woods, former Topshop buyer, reveals how to spot an investment piece
  • READ MORE:  How supermarkets are creating High Street lookalikes you’ll love

Buying on the High Street doesn’t have to mean supporting fast-fashion.

If you know what you’re looking for, and where to look for it, you can discover high-quality gems that will stand the test of time – and the washing machine.

As brands gear up to cash in on Black Friday by offering (sometimes ludicrous – PLT, that’s you with ‘free’ items – think of the real cost) offers, it’s a good time to pause before heading to the checkout with a basket of clothes you might never wear.

Instead, go hunting for investment pieces (yes, on the High Street). As a former buyer for major brands including Topshop and Whistles, I spent 20 years learning what would sell and why. And the pieces that return to the stores year after year, are the ones that are made well – because they last.

Now as the founder of Positive Retail ( – three stores and an online shop offering curated resale fashion for men and women (Prada, Celine, Burberry, Stella McCartney, Gucci) – I know what buyers look for.

Anna Woods has revealed her top tips to ensure your high street purchases are the best possible quality

As a former buyer for brands including Topshop and Whistles, Anna Woods, 41, spent 20 years learning what sells and why 

Here are my top tips for buying investment pieces on the High Street…

Don’t follow fashion

An investment piece is something you will wear time and again; the latest must-have it is not. 

Instead, think about classic styles with timeless appeal, check the fabric – opt for good quality natural fibres – and make sure the garments have been well made. 

Think multi-occasion blazers, cashmere sweaters, tailored shorts or trousers, as well as chic shirts and leather boots.

Avoid the sales

There’s myriad reasons certain clothes are in the sales; one is they’re badly made. What you won’t find in the reduced section are the High Street best-sellers that are re-released every year. 

Tempting as it is to pick up that £1 T-shirt, rather than forking out £40 on another that at a quick glance looks exactly the same, don’t. 

Anna founded Positive Retail ( which offers resale designer fashion for men and women

The problem with cheap items including T-shirts is not only will they not last as long, so you’ll be back at the shops a lot sooner than you think, but they are also less resistant to damage, fading and shrinking. 

Opt for fewer items with a better quality and it will work out better in the long run – for your wallet and the planet.

Not all it seams

The seams can offer an insight into how much time and care went into making a garment, so examine them carefully. Fast-fashion tends to use laser cutters to mass-cut a stack of clothes. 

Lie a shirt or T-shirt flat and look to see whether the seams are straight or whether they’re coming in – an indication of poorer quality. 

Choose a shirt that has a fitted look as it’s more likely to have been tailored to your body type. 

If an item is well constructed it will have double seams around the neckline and the hem will be thoroughly sewn down. If they’re not, it could snag. 

Long stitches could also indicate an item has been made quickly.

Do the light test

Anna has three Positive Retail stores and an online shop selling preloved items from designers such as Prada, Celine, Burberry, Stella McCartney and Gucci

Can’t make up which T-shirt to buy – cheap or expensive? If an item is made well, it’s more likely to last longer both in terms of its shape and wear-and-tear. 

For cotton T-shirts, try the light test. Hold it up and if you can’t see through it, it likely means the yarn used is better quality – the material should feel smoother when you run your thumb over it.

Check the fabric

If you want an item to last, the material it’s made from can make all the difference. Look for those that aren’t using entirely man made fibres. 

Wool is a great fabric for keeping you warm, and it also allows your skin to breathe. Thanks to a waxy coating, it doesn’t need to be washed as much. 

When it comes to plant matter fibres such as silk, cotton or viscose rayon, they won’t keep you warm but they are breathable, so good against your skin. 

Synthetic fabrics such as polyester and nylon don’t breathe, so they might start to smell, meaning you’ll need to wash them more often.

Pause before you buy

Positive Retail partners with brands to sell their unsold stock and with the community of sellers to sell their preloved items

Always pause and think before buying an item: do you really need it? Are you going to wear it for the next 10 years – is it going to last that long? Consider what else you would wear with it. 

Ask yourself whether those bright red trousers are really your style; or do those six-inch heels go with your lifestyle. Take a look at the clothes you’ve been wearing over the past five years. 

Don’t just buy things for fashion frivolity – or to fill a void.

Splash out on preloved designerwear

Designer brands tend to honour the design process – sometimes to a totally primadonna level! But it means every level of care and consideration has been put into making that garment. 

If you can afford it, think about splashing out on investment pieces from pre-loved designer shops. 

When I choose items to sell at Positive Retail, I look for designers that have integrity – that the item has been sketched out and has gone through a long process to be made. 

I look for stylish timeless pieces that aren’t fashion-led. I think: will someone wear this in 10 years time? 

Or I choose some items that are about joy and celebration, as that’s important too!

Anna’s much-loved High Street items that have stood the test of time

Topshop Boutique leather shorts

Anna bought these Topshop Boutique leather shorts 12 years ago for £80

Price: Approx £80

Bought: 12 years ago at Topshop Oxford Circus

Material: 100% leather

Washing instructions: Specialist dry clean – but I never have!

I have worn these leather shorts so much! They’re an absolute staple item in my wardrobe.

My winter alternative is my Autograph leather trousers from M&S. I’ve had them for four years and they cost £175.

Topshop Boutique long silk jacket

A timeless style, this Topshop Boutique long silk jacket was purchased by Anna 15 years ago for £70

Price: Approx £70

Bought: 15 years ago at Topshop Oxford Circus

Material: 100% silk

Washing instructions: dry clean only

This style is timeless and looks good with lots of different styles – over a dress, with jumpers and I used it as a coat for summer weddings. I’ve had it dry cleaned and lot and had the seams at the back sewn up. 

Apparently 100% silk on the High Street is now a rarity because of animal rights. You can buy ‘farmed’ silk, but it’s very expensive.

River Island grey wool deconstructed blazer

Anna has worn this grey wool deconstructed blazer from High Street favourite River Island time and again over the past 18 years 

Price: Approx £50

Bought: 18 years ago in Manchester

Material: Wool blend (label faded)

Washing instructions: Machine washable

I have loved this blazer to death! The pockets are in the perfect place and it’s very comfortable – and it looks as though I’ve made an effort. 

I used to wear it to meetings as a buyer’s admin. It was my way of emulating what I saw in the office, but feeling softer and perhaps knowing my rank.

Topshop spotty shirt

Anna’s polka dot shirt was bought from Topshop 15 years ago for £35

Price: Approx £35

Bought: 15 years ago Topshop Oxford Circus

Material: Polyester

Washing instructions: Machine washable

I wear this all year round and I’ve put it in the washing machine so many times – and it’s only just starting to fade! 

I tie it at the front with the leather shorts, wear it over a slip dress or with a thin rollback underneath. 

For me, polka dots will never date – and will never not be in my wardrobe. I’m not huge on wearing colour so this shirt was the perfect way for me to make an effort!

Topshop boilersuit

Price: Approx £35

Bought: 10 years ago Topshop Oxford Circus

Material: 100% cotton

Washing instructions: Machine washable

For an effortlessly cool look, try a boilersuit. Anna bought this one from Topshop for £35 10 years ago

This is from Topshop’s petite range, which, at 5ft 1in, I loved. I love the shape of it and the short sleeves; it’s a classic and the design is perfect. 

Will boilersuits ever not look cool? This was made at a time when brands had an entire technical department with a team of garment technologists who would oversee a fitting process, to ensure each piece would fit properly. 

They would ask models – or us on the shop floor! – to wear, say, a boilersuit, to see how it will wear. There was genuine consideration about this process, because there was integrity plus we didn’t want returns.

Whistles shearling jacket

A shearling jacket like this one from Whistles, bought for approximately £300 seven years ago, adds a little glamour to any day or night look 

Price: Approx £300 (but they retail up to £15,000)

Bought: 7 years ago from a sample sale

Material: 100% sheepskin

Washing instructions: Specialist dry clean

Whistles’ sheepskins are iconic and timeless – they’re the best on the High Street. 

Each season they create an incredibly tight capsule collection of them in very small runs (20-30 pieces). 

I know they don’t make high margins at all on the product but they do it because they have design integrity and want to create beauty. If I had to buy one from their current season it would be this one.

Whistles sustainable cashmere roll neck

This Whistles sustainable cashmere roll neck is brought back year after year

Price: Approx £175

Bought: 5 years ago

Material: 100% traceable cashmere, responsibly sourced

Washing instructions: Hand wash cool

This is the most incredible quality. Five years on, this item has never been marked down in price, and Whistles has stuck to a good formula. 

I’m so pleased to see they still run the exact jumper though I’ll be honest I don’t need a new one yet as this is still in such immaculate shape.

  • Former High Street buying director Anna Woods, 41, from Kent, is the founder of Positive Retail – a chain of three stores and online offering a premium curation of resale fashion for men and women (Prada, Celine, Burberry, Stella McCartney, Gucci). PR partners with brands (to sell their unsold stocks) and with its community of sellers (to sell their preloved items) – providing a premium retail space to honour value and design whilst giving customers a great experience.

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