01 · Retro Structure

Doctor bags, bowling bags, Boston bags

Prada, Miu Miu and Bottega Veneta all showed structured, dome-topped and trapezoid bags for autumn. The press couldn't agree what to call it. Who What Wear put bowling bags on its list of trends to avoid, calling them oversaturated. Google Trends disagreed: searches for the bowling bag were outperforming the doctor bag.

The more useful thing I found was the date. Prada launched its Bowler in 2000, and it became the template for this whole family of shapes. Twenty-odd years later, here we are again.

Search demand for the new versions was building. Searches for the vintage versions hadn't moved yet. That gap is the whole reason I search backwards.

02 · Long & Low

The east–west shape

Céline is currently selling the Le 16 Side-to-Side at £2,700: long, low, short handles. The Boogie, from 2002 and the Michael Kors years at Céline, has the same proportion and the same house language. It still felt oddly under the radar, so it was the first bag I bought.

The Gucci Capri taught me the most. I assumed it was Tom Ford-era. It isn't. I found women on fashion forums talking about buying theirs new from Gucci in 2006, which puts it firmly in the Frida Giannini years.

03 · Big & Slouchy

One trend, five quite different answers

Big, soft, a bit collapsed. I had one rule here: it has to be useful. I'm not buying an enormous bag that's horrible once you put anything in it.

Louis Vuitton still uses Mahina leather, so I don't think the Mahina is “back”. The bag didn't change. The fashion around it did.

The Loewe Anagram challenged my own criteria. The nubuck is exactly the texture I wanted, but is it big enough? Possibly not, and that's useful, because criteria are there to tell you no sometimes. The Boss Orange suede tote is the one I didn't see coming. Not a famous bag, not a model I went looking for. I found it because I stopped searching for names and started searching for characteristics.

04 · More Is More

Shape, surface and movement

Putting these three together made me realise they aren't really three embellished bags. They're three different kinds of too much.

The McQueen De Manta is about shape. It first appeared in the Spring/Summer 2010 Plato's Atlantis collection, and for SS26 Seán McGirr has reworked the silhouette as the Manta. They've dropped the “De”, so if you're searching second-hand, search both. My version hasn't been reissued; the shape has.

The Valentino Glam Lock is about surface: studs, embroidery, beading, chain. There's nowhere for your eye to rest. The Saint Laurent Helena, from SS16, is about movement, with fringe and tassels that swing as you walk. The listing didn't call it a Helena. I worked that out afterwards, from the labels, the stamps and runway images.

05 · The secret one: Croc Effect

What are you actually buying?

Would you pay £7,740 for a crocodile-embossed bag? Not crocodile. Crocodile-embossed calfskin. That was the price that started this category.

On second-hand sites, “croc” can mean three completely different things: genuine crocodile or alligator, leather embossed to look like it, or a synthetic finish. They have different values and different care needs, and genuine exotic skins can come with restrictions when you buy across borders.

So I looked further down the market, at houses like Mulberry, Aspinal of London, Maje, Coccinelle and Brahmin, and then checked what each bag was made of, because the listing title often won't tell you.