On January 9, 2007, Apple introduced the first iPhone with a 3.5-inch display, and the pitch was a pocketable screen. In 2007 that size was considered huge. By September 2014 Apple was selling a 4.7-inch and a 5.5-inch iPhone, and today the iPhone 17 Pro Max is a 6.9-inch phone that measures 6.43 inches tall and 3.07 inches wide. Phones got bigger and pockets did not, which is how I explain the whole category to friends.

The crossbody phone bag is the tidy answer. Bandolier is the name most people know: founder Maggie Drake dreamed up the idea after the birth of her first child, wanting what she called a stylish way to attach her phone to her body. The brand says it was born in Los Angeles in 2013, and each one hides a small wallet for cards, ID and cash. That is the whole appeal in a sentence: phone, cards, both hands free.

October is when I start wanting a real bag again, and leather is where I would begin. Picture her walking to a late lunch in a camel coat with the Michael Kors Jet Set in deep red slung across her chest. The Kate Spade Serena in blush is the softer version, a north/south shape with a front flap. For black, the WANT Les Essentiels Arch is the slimmest on a long thin strap, and the HOBO Cass has a striped woven strap that does the talking. The Reiss Solene in dark green has a gold bead on the drawstring, and the Zadig & Voltaire Rock in cream has silver wings and a chain.

One test before you commit: measure your phone in its case. A pouch for the biggest iPhones needs to be a little wider than 3 inches inside.

A phone wallet on a strap is the most practical shape in this edit, because the cards live in the same place as the phone. The Sak Los Feliz in sage has stitched panels, card slots and a removable strap, so it can also go in a tote when you want it to. The Tory Burch Perry in tan is a long-flap wallet crossbody that holds a phone and cards, and I would wear it with a gray knit and straight jeans for a Saturday of errands.

Take the dressier ones next. The Strathberry Multrees in taupe croc embossing has a bar closure and a fine chain, and the Mulberry Lily in soft taupe has a gold postman lock. Both read as small evening bags, but the chain still keeps your hands empty for a glass and a coat. The Vince in cream croc-embossed nubuck has a buckled strap, which is a nice change from chain, and the Veronica Beard in cognac has a curved flap and a gold snap. The MCM Aren in black monogram leather is the loudest of the group. WANT Les Essentiels does the plain version: a black fold-over wallet on a thin strap.

The check I would make is the card slots. Count them against what you really carry, then see whether the flap closes when the slots are full. A wallet that bulges will pull the strap crooked.

What I would skip: a wallet crossbody with no zip pocket if you carry coins or a key, because they slide into the lining and you will be digging.

This is where the category started. Bandolier built its name on a phone case with a strap, and the brand's own line is that it began with a crossbody case designed for hands-free carry. The Hailey in latte woven embossing has a gold frame and a wide matching strap, and the Hailey in tomato red is the same case in a color that will survive a gray November. I would wear the red one with a black coat and nothing else loud.

Cordée Cases takes it in a prettier direction. The Paris set has a long pearl chain and black heart charms, and the Lima set is orange with a cord strap and a printed scarf accent. Both are listed for the iPhone 17 Air, Pro and Pro Max, so check the model before anything else. The WOLF Mimi is a black quilted case pouch with a gold W, a wristlet and a lanyard. The Aviteur Intreccio is ivory woven leather, and the MAISON de SABRÉ sling case has a card slot and a strap loop for iPhone 17 Pro. The Gerard Darel Ladyphone is the slim black holder with a gold clasp.

Test it like this: put the phone in, hang the strap across your body and bend to pick something up. If the case swings forward when you bend, the strap is too long. Shorten it a notch.

What I would skip: any strap case listed for the wrong iPhone. The camera cutout is the first thing that gives it away.

Not every phone bag has to say phone on the label. A mini crossbody works if it clears the width of your phone, and 3.07 inches is the number I would keep in mind for the biggest iPhones. The Tory Burch Mini Miller is a camera-style black leather bag with an embossed Double T medallion, and the Mansur Gavriel Mini Gaia in chocolate is a slim zip-top with a thin strap. Both stay flat against a coat.

For something with edges, the Kurt Geiger Kensington has an eagle-head lock on black quilting and a chain strap, and the Mulberry Small Darley is a black grained saddle bag with a gold postman lock. The Barbour Daphne in tan is a zip mini with a gold plate, which suits a waxed jacket. Kate Spade's Mini Duo in pink has a crescent shape and a detachable pouch charm, the Longchamp Épure in cognac is a textured flap bag with a gold stud, and the AllSaints Half Moon is a black curve on one strap.

I would hold the phone against the bag's front panel in a shop mirror first. Then check the closure, because a flap that sits slightly open on a big phone is the one that eventually catches.

What I would skip: a tiny bag on a chain you cannot adjust. With a phone inside it will bounce at your hip, and you will end up holding it, which defeats the point of crossbody.

Hands-free carry is the whole reason to wear a bag across your body, and nylon is the easiest material for it. The Kate Spade Sam is a black recycled-nylon north/south phone bag with two zip pockets and a wide strap, and the Michael Kors Jet Set in black nylon gabardine has gold hardware and a logo webbing strap. I would wear either with a puffer and white sneakers for a weekend away.

The Longchamp Le Pliage Extra Small in dark green keeps its leather handles and has a detachable crossbody strap. The small crescent in black recycled nylon is a sling with a long adjustable strap, and the Dagne Dover Mara is a sporty neoprene phone sling with a zip top. For travel, the TUMI Voyageur Persia has zip pockets and clip hardware, the MZ Wallace Metro is a flat quilted nylon with a front zip pocket, and the Fjällräven High Coast is a gray recycled-nylon pocket bag with a fox logo patch and a convertible build.

The test is the strap. Wide webbing sits better under a heavy coat than a thin cord, and an adjustable buckle lets you move it over a bulky sweater. Zip everything and tilt it upside down once.

What I would skip: a flat nylon sling for a phone in a thick case. Ask whether the zip closes without a fight.

If I were choosing, I would start with how I really carry things. Phone and cards only, a wallet crossbody like the Tory Burch Perry. A phone that lives in a case, a strap set like the Bandolier Hailey. A weekend away, nylon.

Then I would measure my phone, inside its case, against the pouch. That 3.07-inch width on the biggest iPhone is a good thing to know before you fall for a slim shape.

In 2007 the screen was 3.5 inches and a pocket was enough. Nineteen years later, I would rather keep my hands free.

If you would rather have a shoulder bag with a metal strap, I also gathered chain strap bags, including quilted leather styles.