Think in outlines
Look at the shape of the collar and heel as well as the colourway. Those features remain visible even in a restrained colour combination. A relaxed straight leg can frame the shoe differently from a cropped hem; neither needs a complicated outfit to work.
Before choosing a pair
Check the exact model, sizing system and materials. Use clear photographs and the manufacturer’s product information to compare editions. If you can try the shoes on, do so with the socks you plan to wear. A familiar size or an attractive colourway cannot tell you how a particular pair will fit.
Make it part of your rotation
Try the pair with two outfits you already own. Consider how much care its materials require and where you expect to wear it. Keep cleaning advice specific to the material: leather, suede, mesh and knit should not automatically receive the same treatment.