Designed by Robert Dumas in the 1930s, the bag had a quiet first life. Then in 1956 a photograph of Grace Kelly carrying it was published around the world, and Hermès named it for her. One picture, and a saddlery bag became the Hermès Kelly bag. It is a small, true story about how a thing gets its name, and the myth that it was a magazine cover is just that, a myth. The photo ran inside the issue.

I like the house behind it. Robert Dumas, the son-in-law of Emile Hermès, took over the business in 1951, and the family trade was harness and boots. The Kelly is a shrunken descendant of the old saddle bag, with a belt, a lock and a handle you grip like a rein. Hermès describes it as thirty-six leather pieces assembled by one craftsman, with six hundred and eighty hand stitches, sixteen small studs, a padlock, a swivel clasp and a clochette. That is a lot of effort for a bag that looks so calm.

First up is the Kelly 25, the size I would point most people toward. In my head she is walking to a Monday meeting in October with a camel coat, and the Kelly 25 in noir Epsom is stiff, shapely and pristine. The etain and beton Togo ones are the soft gray answer to black, and I would wear either with a navy knit and loafers. The vert verone Swift is for the friend who dresses in neutrals and wants one loud thing. The Sellier 25 in apricot chèvre chamkila has a warmer, almost suede-like feel, and the bleu marine alligator is the dressy one.

All eight are pre-owned. Check the corners, the handle, the turn-lock and whether the clochette, keys and lock come together, since they should match.

Size is how the Kelly is named. A Kelly 28 is 28 centimeters across the base, and that extra three centimeters over the 25 is the difference between a notebook that fits and one that fights the flap. Both sizes hold the daily things like a notebook, a makeup pouch and small accessories without feeling bulky. For a weekday bag I find the 28 the easier one to live with.

Two builds appear here. The Sellier is structured, with visible topstitching, and often comes in firmer leather such as Epsom. The Retourne is turned inside out after sewing, so the edges are soft and finished with piping. The black Epsom Sellier 28 is the formal one, and the Grace Kelly one too, since Sellier was her preferred style. The etain Clemence Retourne 28 and the gold Togo Retourne 28 slouch just a little, which I would want with denim and a gray sweater.

For color, the rouge pivoine and vert criquet Epsom are the ones I would pick for a gray coat day, and the etoupe Epsom is the safe, lovely middle. The Verso in Evercolor is two-toned and a quieter surprise. The jaune d'or and menthe Sellier with its horseshoe stamp is happy and a bit odd, which is why I like it.

At the fitting stage, hold the bag by the handle and lift it. It should feel balanced, not tipped forward. Open the flap and look at the corners, then check the turn-lock closes without pushing.

What I would skip: a bright color if your whole closet is camel and black, because you will reach for the black one anyway.

Togo, introduced in 1997, is the most popular leather for the Retourne because of its soft, scratch-resistant grain. That matters more as the bag gets bigger. A Kelly 32 or 35 is a work bag, a weekend-away bag, a bag that sits on the train seat next to you, and a grain that forgives scratches suits that life.

The etain Togo 32 and the etain Togo 35 are the same gray in two sizes, so you can see how much room a few centimeters give. The 35 in gold Clemence with palladium hardware is the warm tan option, and the iris Togo Retourne 35 is purple-blue and rare in a good way. If you want the old school look, the vintage black box Sellier 35 and the noir box calf 32 are smooth and a little severe. The lime Epsom Sellier 32 is the joke in the group, in the nicest sense, and the rouge vif Courchevel Sellier 32 is the red one I would wear with a black coat and nothing else.

The condition notes here run from good to excellent, so I would run a thumb along the base, the corners and the handle. Restorers generally replace handles instead of cleaning them, which is why wrapping the handle in a Twilly is a smart habit.

What I would skip: the biggest sizes if you are under five foot four and plan to carry it on your forearm all day. A 32 already makes the point.

The Kelly keeps getting smaller, and it never really stops being a Kelly. The Kelly Cut is a sleek, rectangular clutch for evening, and the Pochette is a flat, slim cousin with a short top handle and the same turn-lock. They are the ones I would reach for when a full bag feels like too much, say a holiday dinner in a black dress and tights.

The two Cuts are the menthe chèvre chamkila and the lime Epsom, both bright and both a little unlikely next to a dark coat. Among the Pochettes, the black Swift is five and a half inches tall and eight and a half wide, which tells you it holds a phone, a card and a lipstick. The rose azalee Swift with gold hardware is the pink one, the feu orange Epsom with palladium is the orange one and the gold Swift with contrast stitching is the warm tan one. The blue Swift is the quiet one. The gris perle ostrich is pale, textured and a bit unusual.

A clutch is a bag you see from the front, so look at the front. On the swift Pochettes look for scuffs at the base and marks near the turn-lock, and on the ostrich, look at the quills for even pattern. With the lock, make sure it clicks cleanly and the flap sits flat.

What I would skip: a Pochette as your only bag on a travel day. It is a bag for the evening and the second bag.

Not every Kelly is a Kelly 25. Hermès has kept the flap, the turn-lock and the silhouette, and stretched them into new shapes. The Kelly Danse was designed by Jean-Paul Gaultier in 2008 with a long strap and a relaxed silhouette, and the Kelly Wallet To Go, a wallet-on-strap with a removable crossbody option, came in 2020. The Kelly Danse II here is the descendant, a navy Evercolor crossbody with a strap drop of about twenty-three inches.

These are the ones I would give to a woman who walks everywhere. The two Elan shoulder bags, one in blue chèvre chamkila and one in blue Epsom, are slim at six by eleven inches and carry the Kelly flap. The Moove in gray Swift is smaller and a very neat little bag. The Lakis 28 in toile and brique is the canvas and red-brown mix. The Depeches 25 pouch in bleu orage Togo carries a name that goes back to the sac à dépêches, the bag that was redesigned in the 1930s and began all this.

The Wallet To Go in jaune bourgeon chèvre mysore and the one in metallic argent are the easiest to wear, because they are tiny and a chain does the job. In October I would put the silver one over a black knit and the yellow with navy.

Try the strap length on your own body, and look at the chain links and the point where they join the bag. Open the flap and see if the lining holds a card or two.

What I would skip: the little crossbodies if you carry a laptop. They are for evenings and errands.

I would start with a size and let the color follow. For most days that is a 25 or 28, in black or etoupe, with a Sellier build if you like a sharp edge and a Retourne if you like it soft. Then read the condition notes, look at the handle and the lock, and wrap the handle in a Twilly from the first day.

If a second one joins the first, make it the small and odd one, a Pochette or a Wallet To Go, in a color that makes you smile in the cold months.

It all began with one photograph and a lady hiding her bump. A bag that famous for being in the right place at the right time is still one of the best at being quietly useful. If you want to keep browsing, I also put together Cartier Necklace and Gucci Perfume, Starting From a Scarf Made for Grace Kelly.