Gucci opened its first boutique in 1921 on Via della Vigna Nuova in Florence, and the house was founded by Guccio Gucci, who had worked as a porter at The Savoy hotel in London from 1897. By Gucci's own account he returned to Florence in 1902 dreaming that luggage would one day bear his name. I like starting there, because it reminds me this was a travel house before it was a shoe house. Footwear came later: Gucci says it introduced it in 1953, most notably with the Horsebit 1953 loafer.

 

That is the pair I think about when someone searches for Gucci loafers women can wear to work. The horsebit on the vamp is a nod to horseback riding, which Gucci says the house started using in the early 1950s to evoke that life and style. The double ring and bar is inspired by equestrian heritage, and Gucci says the loafer is handcrafted in Italy from supple leather. The Metropolitan Museum of Art's Costume Institute holds a pair of Gucci loafers dated ca. 1972, so this shape has been taken seriously for a long time.

 

The first grid is the loafer in its purest form. Start with the Horsebit Loafers and the Jordaan Horsebit Loafers if you want the shape exactly as you picture it. The Jordaan Soft Loafers and the Jordaan Doria Loafer Flats look slightly easier to slip into, which matters on a Tuesday morning. If you like texture, the Suede Horsebit Loafers and the Sylke Horsebit suede loafers in brown are the ones for gray flannel trousers and a camel coat. The Boulevard leather penny loafers in black are the plainest pair here, and they are the one I would put with a white shirt and straight jeans.

 

Then there is the fun end. The GG Embellished Horsebit Loafers and the Horsebit GG Canvas loafers in beige and black are for days when the outfit is quiet and you want the shoe to talk. The white Jordaan Soft Horsebit leather loafers are a summer pair, best with cropped trousers and bare ankles. Try them with the sock you plan to wear, and walk across the fitting room twice. A loafer should stay on your heel without a grip from your toes.

Now the flat mule. If you only know Gucci mules women wear on the street from photos, the backless slipper is the one to look at first. Grazia reports that the Princetown, a backless, shearling-trimmed loafer, debuted in Alessandro Michele's first Gucci collection, Autumn/Winter 2015, which was a men's show. Michele is listed by Gucci as creative director from 2015. Grazia also says Vogue dubbed the Princetown the shoe of the season when it launched. I find it a charming bit of fashion history, because the shoe started on a men's runway and went straight into women's closets.

 

This second grid is all flat. The Princetown Mules and the Princetown Horsebit Mules are the straightforward versions, and the Mules with Horsebit gives you the same ring and bar with a slightly different profile. The Princetown GG embellished mules in blue are the pair to wear when everything else is neutral. For evenings, the GG Crystal Horsebit Mules and the GG Crystal Princetown Slippers have the sparkle, and I would wear them with a slim black trouser and nothing else loud.

 

I like the softer, more relaxed side of the Ragazzo group: Ragazzo Horsebit leather mules in black and Ragazzo GG canvas mules in beige. The Princetown slipper with pearls adds a light-blue GG denim note when I want the mule to feel more playful. The GG Supreme Horsebit Slippers and the GG Supreme Horsebit mules in beige share a monogram print that looks best with plain denim. And the Larindo Horsebit shearling-lined leather mules in black are the cold-weather option, one I would wear with thick socks around the house and on errands.

 

My fitting-room test for a backless mule is simple: walk to the end of the room and back. If your heel slides off the back or your toes grip the sole, try another size or style. A flat mule should move with you, not against you.

The third grid gives you height, and it is not flat, so I would not wear it the way I wear the flats. Platform loafers, lug soles and heeled mules all change the way you stand, so give yourself a few walks around the house before the first outing. A little height can make a loafer feel dressier, and I have found these styles pair well with straight trousers that hit just at the ankle.

 

For platform loafers, I would look at the Brittany Horsebit leather platform loafers in brown, the Rhody Horsebit suede platform loafers in brown and the Rhody Horsebit leather platform loafers in black. The Lug Sole Horsebit Loafers are the more rugged choice, with a chunkier base that suits rainy city days and a long coat. If you want a mule with a lift, the Rhody shearling-lined leather platform mules in black are the winter pair, and the Horsebit GG Canvas wedge mules in beige are the lighter one for summer.

 

The heeled mules are where the mood changes. The Signora Horsebit leather mules in white, the Bamboo leather mules in black and the Double G leather mules in black are the ones I would wear with a slip dress or a silk skirt. The Marmont Double G GG canvas mules in beige look more casual. The Patent leather platform mules in red and the Castello calf hair mules in pink are for people who like a pop of color at the feet.

 

What I would skip: wearing a new platform for a full day of walking before you have tested it, and wearing a heeled mule on slick stone or wet floors. A leather sole can be slippery, and Wirecutter notes that the rubber layer adds grip. I would also skip pairing a very heavy sole with a very long, wide trouser, since the hem can catch under the sole.

So how do I choose a pair of Gucci loafers for myself. I ask three questions. Where am I walking, how long am I on my feet, and what will I wear them with. If the answer is a desk, a train and trousers, I would go for a flat Horsebit loafer. If it is a weekend at home, a backless mule is lovely. If I want height and a little drama, a platform. The short grid at the end repeats the shapes in other colors: the green Horsebit loafers, the black Horsebit loafers on a chunkier sole, the black Brittany platform loafers and the white Double G mules.

 

Break them in first. Wirecutter's cobbler experts recommend breaking shoes in and confirming comfort before adding sole protectors, since protected shoes may not be returnable. Wirecutter also says leather-soled loafers and flats wear down quickly, and that cobblers recommend adding a thin rubber protective sole. That is practical advice I plan to follow once a pair has passed the fitting-room test.

 

My final rule: wear them often. A loafer that sits in a box teaches you nothing, and one you wear every week will tell you what you need to know. If you want to keep browsing, I also put together Silver Heels and Mules.