Grid two is where the sneakers get techy. I am not a runner, and I will say so, but I wear these more than any other pair on a travel day. The Vomero is the one I keep coming back to. Nike's product copy says the V2K remasters the Vomero in a look from an early aughts running catalog, with translucent plastic accents referencing the Vomero 5. That is exactly why it works with a bias skirt: it looks like something from the early aughts you found in a drawer.

The Zoom Vomero 5 shows up in two colours here, a pink-trimmed white and a beige and gold one. Zoom is a technology name, nothing more, and I only care how the shape reads. It is chunky without being clownish, and it sits well under wide trousers. The Zoom Vomero Plus Sneakers and the Vomero 18 Sneakers are the same family in newer clothes, so try them against your usual jeans hem. If the shoe swallows the hem, go for a slimmer cut.

The P-6000 Sneakers are the one I would hand to someone who says sneakers are boring. They carry the metallic, layered runner look and work with a long gray skirt or a pair of faded jeans. The Pegasus Premium Running Sneakers are the more restrained pick, a good one under a trench.

Then the odd ones. The Red Rejuven8 Run OG Jelly Sneakers and the Off-White Rejuven8 Run OG Jelly Sneakers are the playful pair, a see-through jelly feel that looks best against something plain, like a white shirt and straight jeans. Black & Green Total90 Shox Magia Sneakers and White & Black Total90 Shox Magia Sneakers bring the Shox name, which I treat as a label rather than a promise. The Air Max Muse sneakers carry the Air Max name. Nike says the Air Max 1 was born in 1987 when Tinker Hatfield, inspired by Paris's inside-out Pompidou building, exposed the Air unit. I love that a building started it. The Free Metcon 7 Sneakers are the most gym-minded pair here, so I would wear them with leggings and an oversized blazer. The V2K Run in Sail and Coconut Milk is the one that makes the V2K line above true, and the V5 RNR pairs in white silver, off white and blue, and crimson and orange are the Vomero 5 shape in lighter clothes. The running shoes at the end, from the Pegasus and Winflo to the Structure and the trail-ready Zegama, are the honest choice if you actually run, and the Air Max Plus, 270 and Moto 2K pairs are the chunky air-cushioned ones for a travel day.

The last grid is only four pairs, and I want to give it room: the Air Rift split-toe sneakers. The split toe is the whole point. The big toe sits in its own section, so the front of the shoe looks like a cleft hoof and the side view looks like a sock. It is odd, and that is why I like it. The Air Rift is the one pair here that makes people look down on the street and ask what you are wearing.

Start with the White Air Rift Breathe Sneakers. White is the easy way in, because the shape does the talking and the color stays calm. I would wear them with cropped straight jeans and a plain tee, or with a slip dress and a cardigan. The Air Rift sneakers are the main version, the one to pick if you want the plain shape without a gimmick. The Aqua Rift sneakers add a cool, watery color that works with white linen or faded denim. The Rift Satin sneakers are the dressier take, with a satin finish that sits well with a slip skirt.

My fitting-room test is simple. Stand in them in front of a mirror with the pants you plan to wear, and look at the toe split against the hem. A cropped hem shows the shape. A long hem hides it, and then you have bought a plain sneaker with extra steps. Wear a thin sock, or a sock made for split toes, and walk across the room before you decide.

What I would skip: a thick sport sock that bunches in the split, and a very long wide hem that covers the toe. If you want the split to read, show your ankle. Also skip these on the day you have a formal dress code, since they will draw every eye in the room.

Here is how I choose one pair. I ask where I will actually wear it. If the answer is everywhere, I go to the classics: a Cortez, an Air Force 1 or a Dunk Low. If it is travel and long walks, I look at the Vomero grid and think about my hem. If I want one bold choice, I look at the Air Rift.

Then I do the closet test. Pick three outfits you already own and hold the shoe up against each. If it works with two, buy it. If it only works with one, put it back.

One practical note from Nike itself: it does not recommend putting sneakers in the washing machine and advises washing by hand instead. It suggests cleaning about every two weeks or whenever they look dirty, and says many shoes need at least 8 hours to air dry. Good shoes last when you treat them like good shoes. Wipe them down, let them rest, and wear them with jeans on the weekend. If you want to keep browsing, I also put together Nike Moon Shoe and Tennis Shoes.