Guccio Gucci opened his house in Florence in 1921, and for its first decades Gucci was a leather goods maker before it was anything else. One of its bags was called the Fifties Constance. Then Jackie Kennedy was photographed carrying it, again and again, and the bag became the Jackie. That is still the Gucci bag women ask about first.

In 2020 Alessandro Michele brought it back as the Jackie 1961, in mini, small and medium sizes, and it has stayed in the line ever since. It sits under the arm like a soft crescent and closes with a metal clasp at the front.

This grid is all Jackie. The Jackie 1961 mini in black canvas jacquard is the evening one, and the Jackie Slim in white logo jacquard is the summer pair. The Jackie 1961 Slim Small in beige is narrow and neat. The brown Jackie 1961 and the medium beige one are the everyday sizes, and the large black canvas Jackie is the one that fits a laptop. The coated canvas Jackie in beige is easier to wipe clean, and the small textured-leather Jackie in dark brown is the most grown up of the lot.

Try the strap length in a mirror. The Jackie looks best when it sits tight under the arm, not halfway down the ribs.

Gucci first used the horsebit, a small metal snaffle from riding tack, on a pair of loafers in 1953. Two years later it went onto a bag, and the Horsebit 1955 still carries the same hardware across the flap.

The red leather Horsebit Ristretto is long and slim and hangs from a silver chain, so it reads dressier than the canvas ones. The medium Horsebit 1955 in white textured leather is the summer one and looks lovely with linen. The two Ristretto Horsebit bags in brown canvas jacquard are smaller and rounder, and one is embellished for evening.

The GG Marmont is a newer story. It came out on the autumn 2016 runway, named after the Chateau Marmont in Los Angeles, with a flipped double G and quilted leather. The black GG Marmont is the safest bag in this whole edit, and the pink one is the fun version. The two Jetset GG Marmont bags in black add a Web stripe trim and a suede trim, so they feel a bit more casual.

Quilted leather shows dents if you overstuff it. Keep a Marmont for phone, cards and keys.

What I would skip: wearing a Horsebit bag with Horsebit loafers and a Horsebit belt. One horsebit per outfit is plenty.

In 1947 Gucci made a bag handle out of cane, shaping it over an open flame until it curved. That Bamboo handle became one of the house's signatures, and the black Bamboo leather shoulder bag here is its most direct heir.

The Diana small tote in brown textured leather is the other top handle, a structured bag that looks good with a coat. Then the Ophidia, which first walked in Gucci's Cruise 2018 show in Florence with the green and red Web stripe and the double G. The beige Ophidia shoulder bag here has both, and it is the bag I would choose for travel.

The rest are totes for real days. The Giglio comes in small and large in beige canvas jacquard, and the large one is the one I would carry to work. The Savoy tote in beige is roomy and soft, and the Tribecca canvas tote in cream is the lightest, very good for summer. The coated canvas-jacquard tote in beige rounds it out, a sturdy everyday bag.

With a big canvas tote, pick a smaller pouch inside for the things you lose, like keys and lip balm.

What I would skip: a bamboo handle in the rain. Cane can mark and crack if it gets soaked.

Gucci has changed hands creatively three times in a few years. Sabato De Sarno showed his first collection in September 2023 and made a deep red, Rosso Ancora, the colour of the moment. He left in February 2025, and in March Kering named Demna as artistic director, the first non-Italian to lead the house since Tom Ford. Through all of it, the small bags stayed in the line.

The GG Marmont mini bucket bag in black matelassé is the one I would wear to dinner, small but with room for a phone. The Ophidia mini in brown printed canvas is the travel crossbody, and the GG Emblem mini in beige carries a neat logo plaque. The Gossip mini in beige coated canvas is round and playful.

The Mini shoulder bag in cream coated canvas is the simplest, and the Borsetto Small in black leather is the most minimal piece in this edit. The Camera Case in brown canvas with a Web trim is the practical one, flat against the body. The Dionysus small in beige has its tiger head clasp and suede trim, for nights out.

Wear a crossbody across the body on the opposite hip. It looks more relaxed and is safer in a crowd.

What I would skip: a mini bag as your only bag on a travel day. You will end up with a tote anyway.

Some of the best Gucci bags are no longer made, and the only way to get them is pre-owned. This grid is a small archive of pre-owned pieces, and each one is basically one of a kind.

The red Jackie Hobo is the older, softer version of the Jackie 1961, and it makes a strong case for the original. The red Bamboo Daily Handbag is the cane handle in a softer, more casual shape. The black Horsebit Shoulder Bag, in GG canvas with a small chain under the bit, is the everyday bag of the group, and the 1931 Stirrup Handbag in brown takes its name from riding gear, like the horsebit.

The red Boston Bag is a little duffel with a top zip, very good for a weekend away. The Sukey Tote with cream handles is soft and easy, the Mini Ophidia Crossbody in neutral is the small travel bag, and the pink satin Dionysus is the party one.

Read the condition notes closely and look at every photo, especially the corners, the handles and the inside lining. Those are the spots that wear first.

What I would skip: a pre-owned bag with no interior photos. If the seller will not show you the inside, move on.

If I could only have one, it would be the Jackie 1961 in a medium size, in brown or black. It goes with jeans, with tailoring and with a summer dress, and its story is the one I like best. Next would be a black GG Marmont for evenings, then a pre-owned piece that no one else will have.

Gucci's designers will keep changing, and each one will bring new bags. The Bamboo, the Horsebit and the Jackie have outlasted all of them so far. If you want to keep browsing, I also put together Secondhand Gucci Marmont, Ophidia And Soho Bags and Gucci Bamboo, the Scent Named for a 1947 Bag.