September is a big month in the fashion world. Autumn/winter collections appear in store, runway shows take place around the globe and (historically) magazine companies publish their most substantial issues. There is a huge emphasis on new, new, new. But we also have Second Hand September.
This year Richard E Grant is the face of the Oxfam campaign, ‘I’d been an unemployed actor for nine months in 1985, working as a waiter, and I’d bought a second hand raincoat in Oxfam,’ the 69-year-old actor states, ‘which I then wore to my first film audition for Withnail and I, 40 years ago…which then changed my entire life. So I owe it to Oxfam, and I owe it to that raincoat.’
Indeed. Second-hand is for life, not just September. So, I thought it would be good to speak to vintage sellers who work tirelessly, all year-round and are long-standing believers in sustainability. Here, four experts share their advice on shopping vintage clothes, both online and in-store — from what to look for, to how to spot quality, to the best places to start.
Donna Grimaldi, 49,
Is the founder of Bobby & Dandy, a vintage store selling French workwear, utilitarian pieces and a selection of beautiful mid-century American items. With a shop in Hastings Old Town and a well-stocked website.
A vintage seller for over 20 years, Donna’s personal style is also reflected in the clothes she loves to showcase, ‘My passion is for the 1940s and 1950s, split between tailored femininity and mid-century casual wear. For a classic look, I’m at home in an authentic cotton day dress from the era, accessorised with a stack of vintage Bakelite and celluloid bangles, as I absolutely adore bold American mid-century design.
On more casual days, I lean toward utilitarian pieces like original 1950s denim or dungarees paired with a vintage college sweatshirt or timeworn, super soft vintage tee.’
Her advice on shopping for vintage clothes:
Look to the experts.
‘I always recommend sourcing from credible, experienced specialist dealers who thoroughly understand garment history, fabrications, and accurate dating, as well as honesty regarding condition and who provide precise measurements.’
Change your viewpoint.
‘Online vintage shopping requires a shift in mindset as it is completely different from the instant gratification of high street retail. Finding the perfect piece, especially when accounting for vintage sizing and condition, requires patience, persistence and a willingness to enjoy the hunt.
Andrea Maloney Richards, 62, founder of Dede Lost & Found. She sells at pop-up events in London.
The name of Andrea’s small business honours her parents, Denis and Dorothy. ‘I learned everything about dressing well from them, and knew that I had to acknowledge that somehow in my business name. They always looked impeccable despite only having a small selection of clothes. Dad and most of my mum’s family always called her ‘D’.
So DeDe (parents) Lost & Found (the garments) was born. Both loved to make an effort when they dressed and not just for special occasions. Denis always wore a trilby and then a Panama style hat in summer, Dorothy rarely stepped out of the house without wearing a headscarf or a simple hat. They were both snappy dressers.’
Shop for the gaps in your wardrobe.
‘First and foremost, find what you need. If you’re new to vintage shopping, try to imagine how that vintage garment will work with pieces you already own. Make sure that it’s a versatile piece that you can wear everyday, dressed up or down. If you usually feel most comfortable in trousers, then the Victorian lace frock probably isn’t going to get that much wear no matter how beautiful it is! Be patient and be prepared to wait until you find exactly what you’re looking for. Shop with intention.
Search out garments with interesting details, in natural fabrics.
‘I always ask about the fabric. ‘Silky feel’ can often mean polyester. If in doubt, ask as many questions as possible to avoid disappointment. It really breaks my heart when I see the mountains of clothes dumped on West African beaches. There are enough clothes already in circulation and no need to produce new clothes made predominantly of plastic.’
Dede Lost & Found will be at Coal Drops Yard as part of Found + Formed (a showcase of circular style) on 16, 17 and 18 October 2026. Andrea will be sharing more details on Instagram nearer the time.
Elisabeth (Ella) Lennard, 53, founder of Ella Pop Shop
In Paris in her early twenties, Ella first became interested in vintage, ‘I moved from a small town and I loved the nightlife in Paris, enjoyed going out. I was looking for pretty outfits of great quality at more affordable prices.’ She has been selling as Ella Pop Shop for over a decade at vintage fairs and pop-ups across London, and has recently stopped selling online.
‘I have to say, it is a huge relief!’ Ella tells me via email, ‘I loved running the website, and trying to make as attractive as possible, but it took up so much of my time, for such little returns. Selling IRL is so much more interesting. You can help people if they have an idea of what they’re looking for, but most of the time, I enjoy showing customers various pieces and making suggestions.’
Think about longevity
‘Look for quality fabrics, great tailoring, things you can keep in your wardrobe and wear again and again. A beautiful silk shirt, a classic tweed blazer, some great 100% cotton denim, a good quality trench, or classic wool coat. I always want to know the exact fabric composition. It really makes a big difference to the quality of item if it is 100% wool, or a blend.
If you choose quality fabrics and timeless vintage pieces from respected brands, then you can mix them with new items from contemporary labels.’
Look at online reviews. ‘Check out the quality of the photos, and if you feel like the seller has given you some love. Did they spend time doing the measurements and providing details? And, of course, is it a decent brand? Then do a quick search to be sure you’re buying at the right price.’
Ella publishes details of her pop-up events on her website HERE.
Sarah Desmeules, 49, founder of vintage clothing and accessory brand, Lady Boo Salutes You:
‘I sell in as many ways as possible. Through pop-ups, Open House and I have a permanent rail at Haynes Lane vintage market in Crystal Palace.’ With almost 20-years experience, Sarah is constantly busy, enjoys sharing the vintage love and engaging with customers, ‘As a seller, I am fascinated by what customers are drawn to. I love offering advice and seeing the garments on a body – and you cannot underestimate the fun of talking to people who see the same joy in something as you do.’
Think outside of the box
‘We tend to get drawn to things that are similar to items we already own. I often tell people to look through the rail, pull out anything that catches their eye and try it on. It’s amazing what you can discover if you stop saying ‘that won’t suit me.’ For customers, buying from a vintage fair or flea market means you get to touch the items and try them on – which means greater confidence. You can tell when someone finds something they love.
Watching their entire body language change (when something unexpected suits them), is the best feeling. Often, I tell customers that ‘it looks like you already own it, because when a garment works , it just works.’
Shopping online: know your measurements!
‘By that I don’t mean measure your body. I advise people to measure an item they already own to compare to the online item. This is because body size is only one factor, some people like form-fitting clothing and others like a looser fit.’
Sarah’s upcoming events:
Lady Boo will be back at The Lazy Flea at Chiswick House and Gardens on 27 September 2026.
She is part of the Better Things autumn curation with remade jewellery and vintage fashion (available online and in the Better Things shop in Forest Hill).
And will be taking over Free the Gallery in Crystal Palace for a two week pop-up from 9 – 18 October 2026. For more information, see Lady Boo Salutes You on Instagram.
Read More: 8 Chic Linen Skirt Outfit Ideas That Make Summer Dressing Effortless
Looking for more outfit inspiration to pair with your vintage finds? Check out 15 Best Summer Birthday Outfits You’ll Actually Want to Wear