When I’m “in the wild” and see a Groton/Andover/whatever sticker, yeah, I get a little emotional. But I like seeing stickers of schools I’ve heard of/applied to for some reason.
When my kids or a niece or nephew would get ready to apply to BS, one of my brothers would send them a shirt from his BS - which was his way of saying- Apply to my school! It was funny because (while we all loved his school ) no one ended up going there. Poor guy but his generosity and enthusiasm was very much appreciated.
My kids and all their cousins wear shirts from a bunch of different boarding schools all the time and they don’t care - which I think is fun.
Two years ago, I was involved in a horrible thread altercation with a student from a well-known BS who (let’s just say) wasn’t a fan of a certain Hidden Gem ( or any HG for that matter ) . My oldest son ( who was home at the time ) read what was said over my shoulder and couldn’t believe it. K1, as many here ( may or may not ) know, is a big school grad who isn’t exactly known for his warm and fuzzy demeanor - nor is he someone you’d want to be stuck in a lifeboat with (says his loving mother) but I was pleasantly surprised when he came downstairs the next morning wearing that particular HG t-shirt . Later that morning he climbed into a boat with his friends from his school and friends from other boarding schools and they were like “Cool shirt” and Go, Gem School (name). No one blinked nor would they.
+1 for the big school crowd. We still have work to do here though… 
Another time, K2 was wearing his BS t-shirt at Five Guys and a charming old gentleman (who was an alum) struck up a conversation with him about his dearest friend - also an alum who had recently passed away. Imagine how nice it must have been for this lovely man ( in his late 80’s ) to share and connect with a current student- especially after losing his dear friend and fellow classmate. It was an unexpected treat for both of them and something K2 still talks about. Turns out this very nice gentleman was a kind of a big deal ( and still is) - even though he likes an occasional Five Guy burger. You just never know who you’ll run into or what will spark a conversation. It’s good stuff.
Certain school decals on expensive cars only bother me when those cars are driven by people who don’t drive or park well. … Obviously, I’m expecting more (LOL) - but instead of being annoyed or put out - do what we do and have some fun with it. You should hear my husband on this topic- he can get it going.
Where we live any BS decal would not get noticed - none of these schools are in the local zeitgeist. When I happen on one (a very rare event), I will strike up a conversation. There’s a beat up old Volvo station wagon parked on a street in NYC - been there for years (moved around to avoid parking tickets of course), with an Exeter decal on the back window. I’m not an Exonian but I get a kick whenever I’m in NY and see it again.
We were in a hotel a small town in upstate NY and when I came down, my kid had just finished chatting with someone - he had noticed her sweatpants (with school name) and told her his son had gone there and was now graduating from college. The dad was excited to see the school name and happy to reminisce. So good things CAN come from “stickers”. 
What schools gives M&M’s? That would woo me! (Jk but it certainly wouldn’t hurt.)
Deerfield gives white and green M&M’s. @GryffinHunter
I didn’t apply to Deerfield. No M&M’s for me sadly.
I’ll have to buy some to sob over as I watch Titanic after I get in to nowhere.
My daughter got the best piece of swag, a nice Underarmour-type long sleeved athletic shirt, from a school she eventually turned down. The shirt was so good she ended up wearing it anyway!
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Berkshire School flat packed a T-Shirt. They also sent some stickers. Tabor sent stickers. Peddie sent a magnet that said “you got in” Peddie also had an acceptance type congratulations video.
Solebury sent a long-sleeved shirt and a pair of gloves, and all the paperwork was in a folder that said “You’re in!”
I’ve gotten a couple sweet form emails congratulating me and reminding me of revisits, all that jazz. He always ends with something along the lines of “You probably got in to a bunch of other schools, but we hope you’ll choose Solebury,” and I’m like “you flatter!” O:-)
Hotchkiss also gives M&Ms!!
Hotchkiss gives M & Ms and the Mars Candy family is a strong alum and supporter.