Jimmy Choo's Eyla pump is chocolate suede with an almond toe and a flared block heel, and the JC monogram is so discreet you have to look for it. Christian Louboutin's Fannylove 85 is the same color with a signature red sole, which flashes when you walk. Santoni's suede mid-heel pump is a softer brown with a tapered toe and a spool heel, and Santoni calls its suede exceptionally supple. Gucci's Vittoria 75 adds gold-tone Horsebit hardware to a pointed toe. Here is the tip: suede shows its depth in daylight, so try these near a window before you decide they are too dark. They read nearly black indoors and properly chocolate outside.

Kitten heels are the easy way into this color if stilettos make you wince. Jimmy Choo's Amelia is a chocolate leather pointed-toe pump on a 35mm heel, with an Italian leather upper, lining and sole. Marc Fisher LTD's Calynna is dark brown leather on a tapered 1 3/4 inch heel, and Pelle Moda's Aeri is espresso suede with a cushioned footbed. Tod's 40 pump is chocolate suede in a slingback shape, with the little logo charm sitting at the side. My tip: wear a kitten heel with a cropped, slightly wide trouser so the ankle shows. A heel this low looks best when there is a gap to see it.

A slingback lets the foot look lighter than a closed pump, and brown makes it look grown up. Manolo Blahnik's Maysli 70 is dark brown suede with a buckle and a slender 70mm heel, handmade in Italy. Veronica Beard's Luciana is tobacco brown suede with an adjustable buckled strap, so you can loosen it by the end of the day. Dolce Vita's Anabel is cocoa suede with a peep toe, and Saint Laurent's Babylone has gold-tone Cassandre hardware on a brown suede slingback. What I would skip: a peep toe with thick tights. Save the Anabel for bare legs, and wear the pointed ones when it gets cold.

Open shoes in brown feel softer than black ones, and these four prove it. Veronica Beard's Gaela is espresso suede on a stacked, slanted block heel with an antiqued gold buckle. Cinq à Sept's Felicity mule is toffee suede on a 3 inch stiletto with a statement bow, which is the fun one here. Totême's Contour mule is dark brown suede with a square open toe and a sculptural set-back heel, made in Italy. Manolo Blahnik's Callasli 90 is brown calf leather with slim straps and an elasticated slingback. Tip: pick a trouser or jean hem that is clearly darker or clearly lighter than the shoe, never nearly the same brown.

Texture is where brown gets glamorous. Gucci's Signora 85 is glossy brown patent leather with a square toe and gold-tone Horsebit hardware on an 85mm heel. Ferragamo's Sara 95 is dark brown croc-effect leather with an oversized Gancio buckle at the toe. Totême's croc-embossed slingback is lambskin on a 35mm heel, crafted in Italy, and J. Reneé's Stasia is croc-embossed with memory foam cushioning and an adjustable strap. A tip for patent: it reflects whatever is near it, so keep the rest of the outfit matte. A wool skirt or plain knit lets the shine do all the talking.

I choose brown heels by the light I will mostly be standing in. Chocolate suede looks almost black at a desk and glows outside, while tan and toffee can wash out under harsh bulbs. Start with a pointed pair in dark brown suede, since it works with denim, wool and dresses alike. Then add texture later, in patent or croc, once you know how much you actually reach for brown. What I would skip: buying a shade that matches nothing you own. If you want to keep browsing, I also put together Chanel Loafers and Coach Heels.