Everything worth knowing about Flared Shorts is below, starting with the part that changes what you buy. Inseam is the whole decision. Two inches changes who the shorts are for. 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: Otte's Boxer With Embroidered Hem Shorts at $380, and eddiebauer.com's Women's Baja Shorts at $30. The first is the considered buy; the second is the one to start with. 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, Otte's Boxer Shorts ($158) 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 12 brands, $20 to $380, all in stock when this was written. We would not buy all of them, and neither should you. wildoakboutique.com's Elliott Polka Dot Shorts at $20 is the low-risk way in, and Otte's Boxer With Embroidered Hem Shorts at $380 only makes sense if this is a category you already use constantly. On flared shorts 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: if you would not buy it at full price, you do not want it on sale.