Jessica Simpson Little Kid/Big Kid Jackie Moc Slip-On

It may be styled like a varsity jacket, but this LRG cardigan has all the comfy softness of his favorite sweater – plus the practicality of being machine-washable.

He'll look casually cool in this rad graphic thermal from Osh Kosh.

He can complete a classic fall look with the help of the big plaid design on this shirt from Nautica.