The Bata Shoe Museum says heeled footwear was worn for hundreds of years across Western Asia before it reached Western Europe around 1600, and that the early versions seem tied to horseback riding and the stirrup. Its director, Elizabeth Semmelhack, has found evidence of heels in 10th-century Persia and believes they probably go back even earlier. I love that. The thing we now save for a dinner table started life as gear for sitting on a horse.

 

Once it arrived in Europe, it got dramatic fast. The Metropolitan Museum of Art says courtiers at Louis XIV's French court were required to wear red leather heels known as les talons rouges, and the fashion spread to the major courts of Europe until the end of the eighteenth century. Semmelhack notes that men's versions were high but blocky, while women's grew increasingly tall and narrow. So when I talk about heels today, I am talking about an object that has changed hands, and genders, more than almost anything in a closet.

 

Start with the pumps, because they are the base of everything else. Merriam-Webster says nobody knows why a shoe is called a pump, which I find oddly comforting. The Veronica Beard Lorena pumps in black suede, with a small cabochon at the toe, and the Sam Edelman Netty in tan suede with a Cuban heel are the tailoring pair: I would wear either with a straight trouser and a crisp shirt. The Jimmy Choo Love pumps, one snake-effect in brown and one croc-effect patent in blue, are for the days when the shoe is the outfit. Keep everything else plain.

 

The Tony Bianco Stevie pumps in black and the Khaite Valerie pumps in beige are the quiet, clean-lined ones, and I can see them under a long coat and nothing else. The ALDO Lala stiletto pumps and the Jessica Simpson Cassani pointed toe pumps are the sharper, more classic shapes. The Steve Madden Larina lace-up ballet pumps are the softer idea: a ribbon wrapped round the ankle, great with a slip dress. Then the odd ones. The Gianvito Rossi Sofia D'Orsay satin pumps are multicolored and made for a night out, the I.N.C. International Concepts Geosepa halter pumps tie at the ankle, and the Jeffrey Campbell Rhian suede thong pumps wear almost like a sandal. Newer in this group are the Mansur Gavriel Kiki in aubergine crinkled patent, the Favorite Daughter Riley in bordeaux and the Christopher Esber Max embossed pumps, with the Jamie Haller Kitty Point in claret haircalf and the Reformation Natasha in wine patent for a night that asks for it. The Sam Edelman Hazel, the Tory Burch pumps with the gold Double T at the toe and the Dolce Vita Kylo in espresso suede with its buckled ankle strap are the easy ones for work. For colour and texture, the Valentino Garavani Enigme 105 in yellow satin, the Victoria Beckham Angle d'Orsay in burgundy and the Toteme 85 in red patent are the bright ones, the Manolo Blahnik BB 90 comes in houndstooth wool, and the Neous Moriah 65 is leopard calf hair. The Jude Blade 60, the Le Monde Beryl Babouche 40 in olive suede and the Nodaleto Dona 50 in coated velvet are the lower pairs I would wear all day, and the Herbert Levine Gather Around ballet pumps are the softest of all. Before you commit to any pair, stand in them for a minute and look at the line from the side.

Strappy sandals are where a little restraint pays off. A good one has one clear idea, and the rest of the outfit should stay out of its way. I like to start with the Nine West Loola ankle strap stiletto sandals and the Steve Madden Davina sandals, the two simplest here. Both go under wide trousers, and both are the ones I would wear to a summer wedding with a column dress.

 

The Tory Burch Strappy Floral 85 sandals and the Tory Burch Pave sandals are the dressier pair. The floral one has the pretty detail, so I would keep my jewelry minimal and wear it with a plain linen dress. The Pave is the one for a black outfit after dark. The Lauren Ralph Lauren Allie stiletto sandals are the clean, sharp version, and I would try them with tailoring or a simple skirt hitting just below the knee.

 

Then there are the sandals with more to say. The Badgley Mischka Remi has an almond toe, rhinestones and a ruffle, which is a lot, so I would let it be the entire event and wear it with something very quiet. The Diesel D-Cocco ankle wrap sandals in brown wind up the leg, and I like them with a short denim hem. The Wild Pair Louudd open toe evening sandals are the party option.

 

The Reformation Nash is the satin one for a dinner, and the Cult Gaia Reign in gold has a sculptural heel that does all the talking. The SIMKHAI and Christopher Esber heels are the strappier party options, and further down the grid the Aquazzura Horizon in multimetal lambskin, the Stuart Weitzman Babette in patent and the Jamie Haller Sparta gladiator, which wraps the ankle, are the polished designer pairs. The MACH & MACH Le Cadeau has a crystal bow at the heel, and the STAUD Freja is a low suede kitten heel with raffia trim. The Coach Margot slip-on kitten sandals are the relaxed one, with a slim, low line that suits a shirtdress or a pair of cropped jeans. The AQUA Darby and the AQUA Diana braided leather mid sandals, both Exclusive, sit in that easier middle zone, and the Sam Edelman Jeanie slip-on sandals are the easiest to pull on. The Stella McCartney Elyse with its silver studs and saw-edge sole, the Ferragamo Douglas in cognac suede with braided raffia and the Schutz Arlene are the platform options. For a party, the Nodaleto Nodstalgia Gemma, the Jimmy Choo Sacora 85 and the Zimmermann Corsage bring the shine, and the Manolo Blahnik Callydra mixes black velvet with gold. The Loeffler Randall Alice 44 and the Emme Parsons Delicat 55 are the lower ones, the Amina Muaddi Lupita 95 leaves the heel bare, the Jimmy Choo Elsy 70 is a pink slingback sandal, the Zimmermann Solstice is all gold straps, and the Paris Texas Lidia 105 is the animal print. The fitting-room test for any strappy pair is the ankle: does the strap sit where you want it, and does it still look good with the hem you plan to wear.

Slingbacks are the shape with the best story. A famous French house dates its two-tone pumps to 1957, with a beige body to lengthen the leg, a black tip to make the foot look smaller and an elastic strap at the back added by the shoemaker Massaro. I would only call them two-tone slingback pumps in a loose sense, but that is the idea behind a lot of what is on the page here. The beige-and-black logic still works.

 

The Jeffrey Campbell Booshky kitten slingbacks are almost a lesson in that idea, natural leather with a black toe cap, and the STAUD Sebastian in black snake-embossed leather is the sharper, dressier one. Black is the dressy choice, and the natural is the quieter one with tailoring or a trench. The Reformation Calista slingbacks in chocolate croc-embossed leather are the neutral for gray flannel and camel coats. The Aeyde Catrina and Camila slingbacks and the Toteme Contour pair are the clean, quiet ones, and the SIMKHAI Jenny in zebra haircalf, the Loeffler Randall Katerina in black suede and the Veronica Beard Luciana in burgundy are the dressed-up ones. The Badgley Mischka Yuan slingback pumps are the dressier choice, and the SCHUTZ Scarlett Sling mid leather slingback sandals are the casual one, easy under a pair of cropped trousers. The JW Anderson buckled suede pair, the Jimmy Choo Amita in frayed denim and the Christian Louboutin Miss Z Slingina, low with its red sole, sit alongside the Manolo Blahnik Carolyne 50 in gold, the Gianvito Rossi 85 in whipstitched suede, the Amina Muaddi Holli Sling 70 and the Aeyde Celeste.

 

The mules are the opposite mood. The MM6 Maison Margiela Anatomic heeled mules have a rounded anatomical toe and an elastic logo strap across the vamp, which gives them an architectural look, and I would wear them with something very simple, like a white shirt and straight trousers. The Toteme leather mules in brown are soft, smooth and pared back, good with a long skirt. The STAUD Brynn 70 and the Le Monde Beryl Petra 70 are snake-effect, the Nodaleto Dona Ruby 50 is crystal-trimmed velvet in deep red, the Jude Cave 65 is brown suede, and the Jimmy Choo Brigitte 100 is the tall satin one for a night out.

 

The Vince Sabra slingback kitten heels in bordeaux are the one to try first. Kitten pairs have a funny origin. The Times says they were conceived in the late 1950s as a starter heel for girls in their early teens, known in America as trainer shoes, and British Vogue says they were popularised on screen by Audrey Hepburn. I mention it because a lower line tends to look relaxed with jeans, and I find that appealing.

 

What I would skip: wearing a brand-new pair for a whole day of errands. A past president of the American Podiatric Medical Association advises avoiding anything higher than two inches, noting that three inches or more shifts body weight forward onto the ball of the foot and toes. Moderation is the point, and it is best not to wear them every day. Save the tall ones for the evenings that ask for them.

Here is how I would choose. Begin with the outfit you already love, then decide what the shoe has to do. If it should vanish into the look, take a plain pump or a black slingback. If it should start a conversation, take the MM6 Anatomic mules or the ruffle sandals.

 

Next, look at the line from the side, since that is how most people see it. Decide between a pointed toe and a rounder one, between an ankle strap and a bare foot. Then try the pair with the exact hem you plan to wear.

 

Last, walk the length of the room and sit down in them. A good pair should make you want to stand up again, and that is how you know you have found yours. If you want to keep browsing, I also put together Black Heels That Go With Everything and Silver Heels.