Five had genuinely never really dressed himself before
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Five trips and scrapes his knees, which Allison declares as a sign that the schoolboy shorts have seriously got to go and that she's taking him shopping. Honestly, this shopping trip was a long time coming anyway and everyone is surprised Allison held out this long.
Then Klaus wants to go, and Diego could use a new knife, and Vanya has been meaning to grab some more socks for weeks and - yeah, it turns into a family trip to the mall for clothes.
Five is lost at all the choices available to him, Klaus tosses clothes like they're playing dodgeball, Vanya loyally mans the shopping cart, and somehow none of them get banned from the store.
- Part 6 of old dog, old tricks