My kids wore matching L.L. Bean sweaters/shirts for their Christmas pictures when they were young. I think they were about 5 and 10 when we stopped doing that.
Now they see the pictures and laugh!
You have to do it as long as possible, my Father’s Day gift to my husband was a portrait of the kids in their coordinating outfits, starting when the youngest were an infant and 2 and stopping when the oldest was around 12 and the youngest were 6. My youngest are twins, and I had them in twin Halloween costumes for as long as I could get away with it, I think they were in kindergarten when they dressed as Ryan and sharpay from high school musical, my son wore a teal sequined vest, bow tie and hat. I went out big.
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My kids were very opinionated about attire. I have one photo with H and S matching and maybe a different one with mr and D matching.
My sister does coordinated family pics – but she coordinates the color, not the clothing itself. It looks like someone cared before the pics were taken, but not matchy-matchy.
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When my kids were young we had several Christmas and Easter matching family outfits from Gymboree, a couple of times from Children’s place. I loved looking at the Wooden Soldier catalog but it was out of my budget. I loved the matching, but also love just coordinated which we did a lot. Dressing my kids was my hobby for several years and I spent a lot of time and money doing it, not that they appreciated it. 
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Without the OP supplying the ages, this thread cannot be very helpful to them.
Though the tangent it’s gone off on is fun!
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That’s awesome!
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Not the question, but for matching Christmas pajamas we like Burt’s Bees.
For my baby granddaughters I buy matching outfits from Monica and Andy and Hannah Anderson.
For mother-son maybe Reyn Spooner?
I think we’ve scared off the OP from this forum forever!
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Then I’ll add this tip for OP (original poster). You could have a dress made from any fabric… with a tie of same fabric for the little guy.
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