The Sam Edelman story starts with horses, not shoes. In 1975 Sam launched his first fashion venture, a line of English riding-inspired footwear made with his father and born from his passion for horses, according to Footwear News. Years later, after a brand failed in 1999, he and his wife Libby left fashion for equestrian ventures, and Sam became a full-time horse trader. I find that detour reassuring. These Sam Edelman shoes come from someone who left the industry, missed it and came back with a clearer idea of what he wanted to make.

 

The company he and Libby founded in 1987, Sam & Libby, was built on a ballet flat. Footwear News says its Chelsea Bow Ballet hit 7 million pairs sold a year after the company's 1992 IPO filing. The Sam Edelman brand itself followed in 2004, and the CFDA says it began with a gap Sam spotted for runway-inspired footwear that every woman could wear. I will leave it at that and talk about the shoes.

 

Since the flat is where the family history begins, it is where I begin too. The Alie Ballet Flats and the Alie Ballerina Slip-On Ballet Flats are the plain, classic shape, and the Ruthie Leather Ballet Flats are the black woven pair with a small bow, which gives a plain flat some texture. The Kasey Flats are a simple black square toe. Then there is the Michaela family, which I find the most playful: the Michaela Mary Jane Flats, the Michaela Buckled Flats and the Michaela Jelly Mary Jane Flats. The strap across the foot does a lot of work with a plain white tee and wide jeans, and the jelly pair looks best with bare ankles in summer. The Essex, the Lana loafer and the woven Marcie are the more detailed end of the flat shelf.

 

Loafers are the other half of this grid. The Loraine group has four versions: the Loraine Almond Toe Loafers, the Loraine Soft Slip-On Loafers, the Loraine Leather Loafers and the Loraine Bit Almond Toe Loafers. I would wear the bit pair with cropped trousers and a blazer, and the slip-on pair with a long skirt. The Louella Leather Mule Flats are for days you want an open back with nothing fussy.

Sam spent time in the horse world, and you can see where it leaks into the boots. Forbes describes Sam and Libby as avid horse enthusiasts and equestrians who have supported horse show jumping events, including the 2023 Hampton Classic. It is no accident that this grid has four riding-style boots: the two Milla pairs, the Porter and the Penny low-heel pair. The Milla Riding Boots, Regular & Wide Calf come in two calf options, which is a detail I always check before I fall for a tall boot.

 

The Milla Boots are the plainer version of the Milla riding pair, so compare the two side by side. I would wear either with slim trousers tucked in, or over a knit dress where the shaft meets the hem. For a sharper line, the Sylvia Pointed Toe High Heel Boots and the Ramona Pointed Toe Mid Calf Boots are the ones I would try with a straight skirt. Stand up in them, walk to the mirror and see where the shaft ends against your knee and your hem.

 

The booties are the largest group, and the Paige and Saige names show up more than once. The Paige Square Toe Block Heel Ankle Booties and the Paige Zipper Booties share a name but not a shape, so check the toe. The Saige Zipper Ankle Booties and the Saige Pointed Toe Mid Heel Ankle Booties follow the same logic: one rounder, one sharper. The Sophi Zipper Booties, the Grove Zipper Short Boots and the Petty Ankle Boots finish the group. A short boot is a good partner for a slip dress and a trench, and the block heels are the ones I would reach for when the sidewalk is uneven. The Wyatt Western Boots take the stable a long way west, while the Harmony mid heel ankle boots and the beaded Sylvia Bloom knee highs are the dressier pairs.

This is the grid where the dressier shoes live. Footwear News says Sam & Libby grew quickly in its early years, driven by its ballet flat, and I think the heel is a natural next step from there. The CFDA says the brand began with runway-inspired footwear in mind. In September 2026, Caleres said Circana ranks Sam Edelman the number 9 volume brand in women's fashion footwear, with the number-1 flat, pump and loafer in that segment through spring. So the flats in the first grid and the pumps here sit in the same family.

 

The Bianka Slingback Kitten Heel comes up in black and in tan here. A kitten heel with a slingback strap is the one I would wear with a trench and straight jeans, or with tailoring when a full heel feels like too much. The Talula Slip-On Pumps and the Summer Slip-On Pumps are the clean, simple shapes. The Hazel Leather Pumps and the Rosa Block Heel Pumps are the ones for an evening out, and the block heel is the steadier shape on a long evening. The Tegan and Netty 2 pairs are the sharper slingback shapes, the Vienna is a pointed mid heel and the Jeanie is a heeled suede mule.

 

The Margeaux pair gives you two ways to wear an open back: the Margeaux Leather Pointed Toe Mules and the Margeaux Slip-On Mule Pumps. I would wear them with a slip dress or cropped trousers, and I would check how the heel sits on a hard floor before I commit.

 

What I would skip: pumps that you have only tried on a carpeted fitting room floor. Walk on something hard, take a flight of stairs, and make sure the heel and the slingback strap stay put. I would also skip pairing a pointed mule with a hem that hits right at the ankle, because it cuts the line.

Here is how I would choose. Start with the one thing you wear most: a flat for everyday, a boot for the cold months, a pump or slingback for dinners and weddings. Pick one shape from that group and build outward.

 

Then do the small tests. Walk across a hard floor in each pair. Look at the strap, the zipper or the buckle and see if it sits where you want it. Check the shaft of a boot against your hem, and check where a loafer or a mule meets your cropped trousers.

 

I like a brand with a story, and this one has a good one: a man who traded horses and came back to make shoes. The Sam & Libby ballet flat began in 1987, and the flats here are its descendants. The shoes are easy to wear with the clothes you already own, and that is the best argument I can make for them. If you want to keep browsing, I also put together Dior Shoes Women Wear Now and Prada Shoes for Women.