The short answer on True Religion Boys Shoes: pick one anchor piece, keep the palette to two colours, and let the shoes decide how formal the whole thing reads. Repeat one element, a metal, a texture or a colour, and an outfit looks deliberate. One piece should lead and the rest should stay quiet; two competing pieces read as an accident. A moulded footbed takes about a week to break in and then lasts years. The groups below run from the decision that matters most to the ones you make afterwards.

What decides this is strap placement, footbed and heel height. Everything else is preference. Two from the first group show the range: Sperry's Striped CVO Sneakers at $33, and ALDO Shoes's Chicsneaker2 at $40. The first is the easy entry point; the second is where the money goes. A moulded footbed takes about a week to break in and then lasts years. A strap across the widest part of the foot is what stops slipping, not a tighter buckle. A higher price mostly buys materials and finishing, and occasionally it buys nothing at all.

A flat sandal reads dressier with a longer hem. From the second group, shopakira.com's AZALEA WANG NADIA BURGUNDY FUR EMBELLISHED STILETTO SANDAL ($80) 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, boots, 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 pieces here from 13 brands, $20 to $528, all in stock when this was written. We would not buy all of them, and neither should you. Sperry's Ventura Sandal at $20 is the low-risk way in, and Cult Gaia's Fiore Loafer at $528 only makes sense if this is a category you already use constantly. Read as a set, they get you close to True Religion Boys Shoes without any single purchase being compulsory. 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: one considered purchase beats three hedged ones.