In February 1955, Gabrielle Coco Chanel introduced a bag named for the month and year it was born: the 2.55. It had a shoulder strap, which meant hands free, and a burgundy lining said to echo the uniforms at the convent where she grew up. In 1983 Karl Lagerfeld followed with the Classic Flap, a tribute with the interlaced chain and the CC lock, and that is the bag the Chanel Maxi flap belongs to. It is the same bag, just a lot more of it.

Maxi is the largest of the six Classic Flap sizes, bigger than Jumbo, and the one I would pick if you actually carry things. The quilting traces back to equestrian riding coats, and each bag is made at Chanel's Ateliers de Verneuil-en-Halatte by artisans with at least four years of training. So the shape is not a trend, it is a very old idea with a very long strap.

One thing to say plainly: every bag in this edit is pre-owned. That means it rewards a slow, careful look. More on what to check further down.

Start here with black, the version that behaves like a coat. The black lambskin Maxi with the oversized gold CC and leather-woven chain is the dressy one. The 2011 black lambskin double flap and the 2012 black caviar with silver hardware are cooler, a bit more downtown. If you wear your bag hard, the caviar with gold hardware is the one I would choose, since caviar leather resists scratches. The vintage caviar with gold hardware, 13 inches wide, suits someone who wants a slightly softer, older look. Wear any of these over a plain white shirt and straight jeans, then notice how quickly the bag does the talking. Tip: doubled, the chain on the first one drops 14 inches, so try both lengths before you commit.

Pale bags show everything, and that is the fun of them. Chanel made the Classic Flap in lambskin, caviar and calfskin, and in light colors the leather type changes the whole mood: smooth looks soft, caviar looks textured and a little sporty.

The white caviar double flap with silver hardware, is the cleanest. Hologram and box are listed with it, which is a good sign. The white calfskin XL Maxi with the big CC logo is louder and closes with a magnetic snap. If you want something calmer, look at the cream Chanel 19 Maxi with its chunky mixed-metal chain, and the vintage taupe-beige chevron caviar with 24k gold-plated hardware, which is the one I would take to a dinner in a camel coat. The blush pink Maxi Jumbo flap with gold hardware is the sweet one, and the metallic silver lambskin from 2011 is a rare bit of fun.

For the test, hold a pale bag up to a window and check the bottom corners and the edges of the flap for gray transfer from denim. Open the bag and look at the lining for pen marks.

What I would skip: the white and pale ones if your daily bag lives on the floor of a taxi. Light leather is for the days you are in control.

Patent is a different animal. It is glossy, slightly stiff and shows a scratch quickly, but it shines in a way caviar never will. Color is where these bags get a personality, and a Maxi gives the color room to breathe.

The black quilted patent double flap with silver hardware is the easy entry, and the black patent single flap is a touch lighter to carry, with a strap drop of 18 inches. The black chevron patent single flap closes with the Mademoiselle lock, a nod to Chanel never marrying, which I like knowing. Then the louder ones: the 1995 Barbie pink patent Maxi with the oversized gold CC and chain-trimmed edges is the Lagerfeld-era look at full volume, and the other pink patent with the chain-woven border is the same idea. The dark olive caviar double flap with matte gold hardware is the grown-up one, the ash navy lambskin is the quiet one, and the red lambskin single flap with a red lining and a half-moon back pocket is the one for a plain black dress.

For the buying test, bend the flap gently and look at the patent along the quilting lines for cracking, and check for light scuffing and tarnish on the hardware. The pink patent here is listed with exactly that, and it is honest.

What I would skip: patent on a freezing commute, since stiff, glossy leather is the least forgiving there.

Vintage Chanel is where the single flap lives. The Jumbo and Maxi sizes were only briefly sold as a single flap and now come only in double flap, so a single flap Maxi is a small piece of history rather than a current style.

The vintage black lambskin single flap, 12 inches wide with a 24 inch strap drop, comes with an authenticity card. The 1990s quilted jersey Maxi, from 1991 to 1994, has a burgundy interior and a gold CC turn-lock, which is a different texture from lambskin. The black diamond-quilted lambskin single flap and the 2009 to 2010 one share that burgundy lining, a nod to the convent uniforms. The 1994 black lambskin with 24k gold-plated hardware and oversized gold CC is the one I would reach for first, with an excellent condition listing. The XL patent single flap is the sleek one, and the black lambskin single flap from the 2010 collection includes hologram, ID card and dust cover.

Check three things on any vintage piece. Look at the gold plating where the lock rubs the leather, run a finger along the corners for worn leather, and test every chain link to see if the leather weave is dry or fraying. Ask for the serial sticker or card too, since older bags can have a different format.

What I would skip: the vintage XL listed as fair, unless you are ready to repair it.

Chanel 19 feels softer and slouchier than the classic. The chain is chunky and mixed-metal, and the Maxi makes it a proper shoulder bag. Reissue is the other route, and it dates back to the 2005 anniversary copy of the original 2.55.

The navy, the pale sage-green and the blue Chanel 19 Maxis all have a strap drop of 14 inches, so they sit right at the underarm. The sage one is the widest, at 15 inches, and is my favorite for a white tee and tan trousers. The black Chanel 19 listed as fair is the one for someone who will repair it. On the Reissue side, the aged calfskin black 227 double flap has a lipstick pocket and burgundy interior, and the metallic dark silver one is the same bag in a cooler finish. The gold metallic and purple metallic Maxi Reissue flaps are the loud ones, both with a thick silver chain and a shoulder drop of 10 inches or 18 inches.

Test the chain on your coat sleeve, because a thick chain can catch wool. Then check the Reissue's aged finish for flaking.

What I would skip: the metallic Reissue if you want a bag that blends in. These are party bags.

I would go in this order. Choose the leather first: caviar for daily use, lambskin for evenings, patent for fun. Then choose the hardware, silver for cool and gold for warm.

Next comes the condition check, the part people hurry. Look at the corners, the hardware, the chain wear and the serial sticker or authenticity card, ask for photos in daylight, and make sure the hologram and dust bag are there if they are listed. A good pre-owned bag should come with a clear account of what was used.

Then carry it. More than seventy years on, Coco Chanel's idea still works: a bag that frees your hands, now in a size that holds the whole day. If you want to keep browsing, I also put together Chanel Bag Dupe and Chanel Flap Bag Guide.