Do these shirts fade as quickly as other shirts do? I use woolite but they still fade

No they do not. I bought uniform shirts from Aeropostale, and they were horrible. Faded so fast. The best uniform shirts by far are Old Navy's. They eventually do fade as all shirts do, but Old Navy has been the best.

does the Dickies Big Boy's 18-20 black shrink when washed?

Following the care instructions on the tag, there shouldn't be any shrinkage and if there is, will be very minimal.

My son is usually a size small or size 5. what size should i get? should i get the small 4 or small 8?

My son is a size 7, and the big boy 7 fit him. If I were you I would select little boy, then 5/6.

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