Jane Birkin carried a straw basket almost everywhere: to the market, out to dinner, onto planes. The story goes that on a Paris to London flight in the early 1980s it spilled open next to Jean-Louis Dumas, who ran Hermès, and the leather bag named after her came out in 1984. I think about that basket every time I pack for somewhere warm, because it is the whole argument for vacation dressing. Pick a few things with real texture, wear them every day, and let them get a little worn in.

 

So this edit is built around the three things I actually plan a trip around. Flat sandals for walking, because you always walk more than you think. Mules for the in between: lunch, a museum, the walk back from the beach. A bag in straw, raffia or rattan that can hold a towel and still look right at dinner. Then a short row of heels and wedges for the nights you dress up.

 

My packing test is simple. I lay every pair of shoes next to the one bag I am bringing, and if a pair does not work with that bag, it stays home. Two flat pairs, one mule and one heel cover a week.

 

What I would skip: anything brand new that you have never walked in for a full afternoon. A cobbled hill is not the place to break in a sandal.

In 1946 a shoemaker named Amedeo Canfora opened a small sandal shop on Capri, across from the Grand Hotel Quisisana, and made leather sandals to measure. In 1962 Jackie Kennedy asked him to open the shop at midnight so she could choose in private, and the simple style he made for her is still called the K. That is my idea of a vacation shoe: flat, plain, and good enough that you stop thinking about it.

 

The thongs here follow that line. The Ancient Greek Sandals Eleftheria and the Black Suede Studio Tres both wrap the foot so they stay put on stairs, the Dolce Vita Tyrice adds an ankle strap, and the Roger Vivier crystal pair is the one I would wear to dinner with a long skirt. For slides, The Row Hugh, the Miu Miu suede footbed and Prada's woven raffia pair are the quiet options, and the TOM FORD julianne is the polished one. For the beach, the Tory Burch Mini Miller jelly sandals and Double T sport slides are easy to rinse and forget, the Birkenstock Arizona in a print is the comfortable one, and the Loeffler Randall Nico brings the raffia story down to your feet.

 

Then a few easy mules for the days you want your heel free: the Moncler Bell in suede, the Di Gaïa Cheryl with its fringe, the Dries Van Noten sneaker mule for a long day of walking, and the Chloé jelly mule in an animal print, which you can wear right into the sea.

 

The practical tip: choose a flat sandal with some structure across the foot, either an ankle strap or a wide band. Thin straps start to rub after a full day on your feet.

 

What I would skip: a sandal with a slick, smooth sole if your trip involves old stone streets. Polished stone gets slippery, and you will feel it on the first hill.

Mules owe a lot to Beth Levine, who designed shoes under her husband's name, Herbert Levine, after the two of them started the label in 1948. In 1952 they introduced the Spring-o-lator, a backless mule with an elastic strip that kept your foot in place without a strap. The label still makes shoes, and the Herbert Levine Sleep On It mule in yellow satin is one of my favorite things in this edit. It is flat, so it works for a full day.

 

For a low heel you can walk in, I like the woven ones best. The SIMONMILLER Knotted Gala looks hand tied, the Jimmy Choo Chara is made of raffia, and the Bottega Veneta Atomic and Lido use the house's weave on a bigger scale. The Khaite Colt is the plain leather pair if you want one that goes with everything.

 

The rest are for the evening. The Givenchy Boudoir Bow, the Roger Vivier Trompette in satin, the Magda Butrym satin pair and the Christian Louboutin Affabula are the ones I would wear with a slip dress. The Gianvito Rossi zebra pony hair and the Valentino Flutterby are for when you want the shoe to be the point, and Amina Muaddi's clear Dalida almost disappears under a long hem. The Schutz Cloe, Tony Bianco Vanquish and SENSO Upton IV are simpler and easy to pack. For a slimmer line, the STAUD Faye and Schutz Loren mid mules are the ones I would reach for, the Tony Bianco Matisse is a wedge mule for cobbles, and the Madewell Lorna Orasay is the flat mule I would wear to the airport.

 

The tip: walk down a flight of stairs in a mule before you commit. A good one stays on without you gripping with your toes.

 

What I would skip: a high mule for a day of sightseeing. Save the tall ones for the evening, when the walk is short.

Bottega Veneta started as a leather workshop in Vicenza in 1966 and introduced its woven intrecciato in 1975, with no logo on the outside, just the weave. That idea, that the texture is the signature, is why I think a woven bag is the most useful thing you can pack. The Bottega Veneta Small Andiamo in raffia and the tiny Wallace are the special ones here, and they look as right with a linen shirt as with a swimsuit.

 

For a beach day you want a basket you can throw things into. The Christian Louboutin Venus, the Manebi Loto and the Mar Y Sol Paros tote all have room for a towel and a book. For lunch and dinner I like something smaller: The Row Alma, the Khaite Billie bucket, the Poolside Josie Knot, and the ALAÏA Le Coeur, a straw heart on a long strap that should not work but does.

 

In between, the ANINE BING Lili in dark brown raffia, the Chloé woven raffia tote, the Clare V. Sandy tote, the SIMONMILLER Lopsy in metallic raffia, Proenza Schouler's raffia bucket, the Loeffler Randall Willow hobo and the Tory Burch raffia bucket cover most of what you would want.

 

The tip: check the handle drop first. If it will not go over your shoulder with a shirt on, you will carry it in your hand all day.

 

What I would skip: unlined raw straw for the beach. Sunscreen and a wet swimsuit can stain it in one afternoon, so look for a lining or keep a pouch inside.

Steve Madden started his company in 1990 by selling shoes out of the trunk of a car to small Manhattan stores, and designers like Betsey Johnson put his platforms in their shows. More than thirty years later his heels are still the ones I tell friends to pack, because they are light and nobody cries if one gets sand in it. The Steve Madden Juni platform in black and the Beki in orange are where I would start, the Tamala is the dressy one, and the Laelia is a raffia wedge that matches half the bags above.

 

If you are walking to dinner, go lower. The Steve Madden Edna in gold, the Betsey Johnson Lesli from Steve Madden, the ALAÏA Infradito in snake effect leather and RAYE's Tahlia, which ties at the ankle, all sit on small kitten heels. The Zimmermann Belara is a wedge, the easiest heel on uneven ground.

 

For a restaurant you reach by car, the Schutz Scarlett, the Jeffrey Campbell Reptilia with its gold hardware and Bottega Veneta's stretch slide in red are the ones with real height.

 

The tip: pack one heel in a color that goes with every dress you are bringing. Black or a metallic usually covers it.

 

What I would skip: thin stiletto heels if dinner is outside. Grass, decking and gravel will catch them every time.

When I pack for a week somewhere warm, the shoes and the bag go in first and the clothes get chosen around them. One flat sandal for walking, one mule, one heel and one woven bag is my starting point, and most trips I come home without having missed anything.

 

If you are building this from scratch, start with the bag, because you carry it every day and it ends up in every photo. Then pick the sandal that goes with it, and keep everything else simple: linen, cotton, a swimsuit, a slip dress. The texture is already doing the work. If you want to keep browsing, I also put together Tory Burch Outlet and Tory Burch Miller Mini Crossbody Bag for Women.