Now the small ones. Harper's Bazaar UK reports that the Baguette first appeared on an autumn and winter 1997 runway, reached stores in 1998, and was a break from the minimalist oversized totes of the Nineties. The house says the name comes from French bread, which is traditionally carried under the arm. That is the whole idea of a baguette: short strap, small body, tucked close. I find it the most outfit-friendly shape there is, because it adds a line without taking over.

The test I use is strap drop. Bag brand Bouclier defines it as the vertical distance from the highest point of the strap to the top edge of the bag when it hangs naturally, and suggests measuring a bag you already like with a flexible tape. Try it. A short drop sits at the hip bone and looks sharp. A longer one rides lower and feels more casual.

Coach has the most here, and they are easy to compare. The Plaza Small Crystal Signature Jacquard bag is the dressy one for evenings. The Demi Small Signature Jacquard bag is the daytime version of the same idea, and the Chelsea Small Leather bag is the plain leather pick. Coach says it was founded in New York in 1941 by six artisans, and I like that these are still built around soft, simple shapes.

Saint Laurent gives you two. The Mini Le 5 à 7 is named, according to Vogue, after the 1962 film Cléo from 5 to 7, and was introduced in the Spring 2021 collection under Anthony Vaccarello. The Voltaire leather mini bag is the quilted-looking, glamorous cousin. The Gucci Ophidia small bag and the Jacquemus Small Oval calfskin leather bag are the two with the strongest personality, and I would let either one carry the outfit.

Then the easier ones. The Tory Burch Romy Small bag, the MICHAEL Zoe Small Leather Convertible Slim bag and the GUESS Jessa Small handbag are the practical trio, and the AQUA East West bag is the clean, wide one. The Gimaguas Mini Franca bag is the playful one, and it looks best with something plain.

Leather is the group I would buy first if I owned only one bag. A structured leather bag keeps its outline when it is full, and that makes it the one for work, travel days and anything that needs to look pulled together. It also pairs with tailoring in a way a slouchy hobo never quite will.

Look at the two STAUD and Madewell pieces first. The STAUD Harlow Leather bag is the clean one, and The Signature Woven Leather Large bag from Madewell is the roomy pick with texture. The woven surface does a lot of work, so I would wear it with simple knits and straight trousers. The Ralph Lauren Collection Leather bag is the quiet one, and I would take it to a meeting with a navy blazer.

For more edge, the Diesel 1DR bag in nappa-leather is the one I would wear with a denim jacket, and the ALLSAINTS Ares Grained Leather bag is the more rugged choice, with a grained finish that hides scuffs. The AQUA Large Leather bag is the straightforward large pick for a laptop and a lunch. Prada's Logo-plaque leather bag is the dressy end, and Vogue reports that Prada revived its Re-Edition 2000 and 2005 nylon bags in 2019, so you know the house has a soft spot for a clean shape. The GIANNI CHIARINI Bloom ostrich-effect leather bag is the textured one, and it works as the single interesting thing in an otherwise plain outfit.

Coach says its Glovetanned Leather was invented in the 1950s by founder Miles Cahn and is named for the baseball glove, as it is soft and durable and develops a patina over time. I like that idea for any leather: you want it to look better after a season of wear, not worse.

What I would skip: a rigid bag that is too small for your daily things. If you have to carry a second tote for the overflow, you chose the wrong size. Also skip anything with a strap that digs into your shoulder when the bag is full. Load it in the fitting room and walk around.

Here is how I choose. I start with what I carry, and I put it all on the bed: phone, wallet, keys, lip balm, something to read. If it all fits with a little room to spare, the size is right. If I have to squash things, I move up a size.

Then I test the strap. I hang the bag on my shoulder, walk across the room and check that it stays put when I turn. I check the drop against my hip, and I check whether a coat sleeve pushes the strap off. Winter coats change everything, so I try the bag over the thickest thing I own.

Last, the mood of the outfit. Soft shapes like the hobos go with simple, relaxed clothes. Baguettes sharpen anything plain. Leather pieces with a structure are for days that need to look organized. Pick the one you will carry on a Tuesday, not only on a Saturday, and it will earn its place. If you want to keep browsing, I also put together The BDG Cindy Shoulder Bag and Balenciaga Rodeo Bag Dupe.