The short answer on Shorts That are Not Too Short: 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 side zip sits flatter than a fly front. The groups below run from the decision that matters most to the ones you make afterwards.

What decides this is inseam, rise and fabric weight. Everything else is preference. Two from the first group show the range: THATS SO FETCH's Steele Shorts - Black at $45, and Alfie's The Boxer Shorts at $279. The first is the easy entry point; the second is where the money goes. A side zip sits flatter than a fly front. Inseam is the whole decision. Two inches changes who the shorts are for. A higher price mostly buys materials and finishing, and occasionally it buys nothing at all.

Longer shorts want a fitted top. Shorter ones want volume up top. From the second group, THATS SO FETCH's University Shorts - Cobalt Blue ($17) 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, shorts, 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 shorts here from 14 brands, $17 to $495, all in stock when this was written. We would not buy all of them, and neither should you. THATS SO FETCH's University Shorts - Cobalt Blue at $17 is the low-risk way in, and us.leolinofficial.com's Tessa Appliqué Vegan Suede Shorts - Azure at $495 only makes sense if this is a category you already use constantly. On shorts that are not too short 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: one considered purchase beats three hedged ones.