Sizing on Sneakers with Star on Side is the part worth slowing down for, because it is the reason most of these get returned. Fit at the shoulder and the waist is hard to alter; length and taper are cheap to change. Brand size labels are not standardised, so the measurements in centimetres are the only comparable number. Repeat one element, a metal, a texture or a colour, and an outfit looks deliberate. The groups below run from the decision that matters most to the ones you make afterwards.

What decides this is last shape, toe box width and cushioning. Everything else is preference. Two from the first group show the range: Kenneth Cole's GENTLE SOULS - Cacti Suede Braid Detail Sneaker Bootie at $143, and alohas.com's Tb.25 Blue Sneakers at $144. The first is the easy entry point; the second is where the money goes. A wide toe box matters more than cushioning if you are on your feet all day. Sneaker sizing runs a half size small across most of these brands. A higher price mostly buys materials and finishing, and occasionally it buys nothing at all.

Keep the sneaker quiet if the rest of the outfit is doing something. From the second group, Kenneth Cole's Alma Leather Sneaker ($88) is the one that earns its place, because it works in more than one context without being restyled. The third group is smaller and deliberately narrower, sneakers, for the decisions you make after the main one. None of this needs the whole group. One piece from each is usually enough.

There are 20 sneakers here from 9 brands, $50 to $445, all in stock when this was written. We would not buy all of them, and neither should you. Sperry's Venice Boat Sneaker at $50 is the low-risk way in, and Jonathan Simkhai's Georgie Shearling Slip-On Sneaker at $445 only makes sense if this is a category you already use constantly. On sneakers with star on side specifically: the difference between the top and the bottom of this list is real but smaller than the price gap suggests. Nothing here is included because it is famous, and price is not used as a proxy for quality anywhere on this page. If you take one thing away: the piece you reach for on a rushed morning is the one that was worth the money.