The Paddington was first seen at Chloé's spring/summer 2005 show, slung on the shoulder of an oversized blazer with a wispy chiffon blouse and a silk skirt. Phoebe Philo was the house's creative director from 2001 to 2006, and she gave the bag a curved east-west shape and a big leather-covered padlock. All 8,000 units sold out on pre-order before they reached the shop floor. That is the story I think of every time I see the Chloé Paddington bag on someone in a coat and boots.

What I love is how little it relies on a logo. You know it by the lock. It was also not an easy bag: the straps only just fit over the shoulder and that lock made it heavy. Chemena Kamali, who started at Chloé as an intern in the Philo era, brought it out of the vault for her Fall 2025 show, with Alexa Chung carrying a burgundy one on the runway. The new bags are considerably lighter, with a lighter padlock and a secured zip.

The first group is the new core. I would start with the Black grained leather one, because it goes with everything in a fall closet: a gray wool coat, straight jeans, flat boots. The Crafty Brown is the deep oxblood-brown one, and it is the shade I would put with a camel scarf in October. The Flannel one in taupe-gray has an antique-gold padlock and looks good against black knitwear. The teal-blue one is the satchel for anyone who wants one loud thing in an otherwise quiet outfit. If you need a smaller shape, the Paddington Vanity Bag in black is boxy and structured.

My practical tip: check the shoulder drop before you commit. Put the bag on over your thickest coat and see if the strap still sits. If you wear a puffer, the handles are the better call.

Suede is the quiet way to do a Paddington. The Dusty Beige is a pale sand suede with rolled handles, and the Vintage Brown is the warm cognac one with C-shaped buckles. The Kohl Brown is dark espresso, the one I would wear with black tights and a chocolate knit skirt in October. All three are calfskin and carry the oversized padlock.

For a hands-free day, look at the crossbody versions. The Paddington Crossbody in suede comes in Vintage Brown and Kohl Brown, with a long strap, and the Kohl Brown has knotted ties as well. Then there are two cream crossbodies: one in shearling, in goatskin, and one in grained leather. The shearling is a cold-weather bag, soft and visibly textured, and I would wear it with an oatmeal coat and gray denim. The grained cream one is easier with a white shirt and wide trousers.

The Grenat is the deep garnet-red grained leather bag, with rolled handles, and it is the one I would pick if your coats are all neutral. Red-brown reads almost like a neutral next to navy.

Fitting-room test: run your hand over the suede in both directions. It should show a soft change in shade, not patches. Hold the crossbody at your hip and check that the strap length lets the lock sit flat against you.

What I would skip: the pale suede if your commute is mostly rain. Choose the grained leather instead.

Kamali's relaunch came in two sizes, small and medium, and the small end has since grown into a whole family. The Small Paddington Sling Top Handle Bag is in soft lambskin, in black and in burnt red, with a drawstring detail and the gold padlock. It is about 10.6 inches wide, so it holds a phone, a card holder and keys, and not much more.

The Mini Paddington Sling Pouch is the one I would pick for a night out. It comes in tawny brown, burnt red and black, with fringe or knotted ties and a strap, and it is under 10 inches wide. I would wear the burnt red with a black slip dress and tights, and the tawny brown with a leather jacket.

If you want the grained leather rather than the lambskin, the Small Paddington Bag with Strap comes in pale blue and in oxblood-brown, and has both a top handle and a strap. The Mustang Brown shoulder bag is the tiny one, with a chain and strap, a caramel color that goes with denim and a cream knit.

The test: load the bag with what you actually carry. Lip balm, keys, phone, a small wallet. If the padlock bulges or the flap will not lie flat, go up a size. Also look at how the strap hangs when the bag is full.

What I would skip: the mini pouches for travel days, when you need a passport and a charger.

The originals have a real history. Vogue's Sarah Mower reported in 2009 that every one of the 8,000 made in spring 2005 was spoken for before it reached the stores. The padlock was the crowning glory, with the key hung from a narrow tie on the handle hardware. So when I look at pre-owned Paddingtons, the first thing I check is that the padlock and key are both there.

These are all pre-owned, with condition grades from Good to Excellent. The 2007 black leather one is a classic satchel with rolled handles, gold-tone hardware and the hanging key. The 2000s light brown tote is grained leather with two rounded handles, and the yellow one has a top zip and an internal slip pocket. The brown 2007 bag has front flap pockets and studs. For something with more weight, the Chocolate calfskin satchel has aged gold studs and side buckles, and the Purple one has tall rolled handles and patchwork detail. The Gris Vert has decorative anchors and silver hardware, which I find unusual. The gray one is from the 2006 collection, with twill lining and a zip closure.

What to check: the corners and handle edges, the lining, the zip, and whether the lock turns. Look for a date code and any papers. A soft, worn leather is part of the charm here.

What I would skip: any bag with sticky lining or a lock that does not close. Those are repair jobs.

Not every Paddington is a satchel. Chloé also made versions in 2010 and 2011, and the pre-owned racks have them. The brown tweed tote from the 2010s is the strangest and my favorite: tweed with leather trim, side buckles and gold-tone hardware. I would wear it with a gray skirt, tights and loafers. The blue calf leather tote has two rounded handles and metal feet, so it stands on a desk.

For a classic shape, the 2000 to 2026 medium brown comes with its padlock and key and an Excellent grade, and the Signature medium in brown is from 2011, with studs and dual shoulder straps. The 2011 black shoulder bag has a front flap pocket and comes with an authenticity card, which I like to see. The creme calfskin tote with a front pocket is the lightest in color and would suit a cream coat.

The two small Paddingtons, in Tulip Red and in black, are grained buffalo leather with anchor handles and a hanging gold lock. The red one is the pick for a plain navy outfit.

Buying test: ask for photos of the base, corners and the inside of the zip, and check every grade against them. Make sure the lock, key and any card are included.

What I would skip: a pre-owned bag with a strong smell in the lining, or hardware that has flaked.

I would decide in this order. Pick the color you would wear every week, then the size, then new or pre-owned. For a first bag I would go for the black grained leather, because it is the shape Kamali relaunched in 2025 and it sits well with the coats in this month's closet.

If you want something with a past, a pre-owned 2000s satchel is the real thing. Check the lock, the key and the corners, and choose the grade you can live with.

Whichever you pick, I would still put it on over a coat first. It all comes back to the lock: heavy in 2005, lighter now, and still the first thing anyone sees. If you want to keep browsing, I also put together Contour Makeup Went From a Kevyn Aucoin Sketchbook to a Stick in Your Bag.