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I don't think it's a good idea to give him an old shoe to chew on. I don't think dogs can really distinguish old from new- he'll just learn to chew on shoes. Can't you get him something that is clearly not a shoe to chew on?
My dog is a kleptomaniac. He takes EVERTHING. And he gets this sly look in his eyes when he does it.
We have a pretty big dog door for him and he takes whatever he can grab outside. Socks, shoes, bras, glasses, towels, pillows, etc. Once I found him with a couch cushion. Not a throw pillow, but the actual cushion that you sit on. He had it halfway through the dog door, but it was stuck and he was using his head to try and push it through. It was very important to him to get this cushion outside.
He's adorable! I love his shag!
Having been through training with my dog, the "old shoes are okay" thing is flawed logic. He's not going to be able to ascertain an old shoe versus a new shoe. Get him a fun and interesting toy that's not apt to be confusing to him. It will save you guys tons of headaches in the future.
our puppy goes NUTS in our backyard. (rabbits climb in under the fence sometimes). She runs around the perimeter of the fence a bunch of times until she's too tired to go on (and she's a doxie, so she doesn't last too long!)
We have a Shiffon, too! (Well, we think he is a shiffon. He is a rescue, but our vet seems to think he might be a mix of those two breeds) While he doesn't go for shoes, he loves to "kill" his toys by rolling on them and shaking them around the house. It's hilarious to watch.
That's exactly what John knox did! He acts like he's going to kill something, then he gets too tired and lays down for a nap (what he's doing currently). Thanks for the advice about shoes...I had no idea! I just figured we had to hide all our good shoes from him for eternity. :)
Must agree with Rosechicklet... You'll find out soon that your dog will not know the difference between Old and New Shoes. Soon enough he'll have your new ones too enless you take them away & disipline him totally.... lol NO MATTER HOW CUTE HE IS!!!!
I have a yorkie and if my purse is on the floor he will route through it and pull everything out for attention!
He wont chew it or anything he will just take it out of the purse (chapstick, pens, receipts, hand sanitizer) and bring it to me and drop it in front of me like "play with me mommy!"
It's so cute! And the fact that he is 14 and still wants to play is amazing!
Cody.jpg (92 KB, 50 downloads) 2 years old 
What really cracks me up about mine is how they act when they know they've been bad and they know that we know it! Our 85 lb. pit mix, he will run behind the couch and peek over the top at us, and when we look at him he will duck his head down where we can't see him LOL!! And the little one, about 25 lbs., well he will just drop down wherever he is at the moment and roll over onto his back - legs up the in the air - (reminds me of a criminal putting their "hands up") with the cutest darn face ever. hehe. They kill me! 
We're trying to train our English Bulldog puppy to not destroy shoes. Actually, it's going pretty well. For some reason he goes absolutely happy-crazy for Kong Wubba's (they come in several sizes, but we give him the large breed one else they'd last like 3 days, seriously). He seems to love it so much more than shoes cause it kinda feels like a shoe (canvas on top of a hard rubber ball), but it squeaks! But yeah, keep all shoes off limits-even old shoes. Good luck-he's adorable!!!
Mine loves to play fetch. Except he hates dropping his toy. So he brings you a toy, waits for you to tug on it, then runs away with it still in his mouth and brings it back. Repeat. It is fetch without any throwing.
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I absolutely love my Shiffon Puppy (Brussels Griffon & Shih Tzu) and I can't believe I haven't brought him up yet on the boards. He has discovered chewing shoes (quite upset when he found my Toms...) and we gave him a pair of FI's old birkenstocks to chew on (yeah, we're hippies with the Toms and Birkenstocks). Anyway, John Knox (my dog) just started growling in the other room and I looked over at him to see him in a fight with FI's shoe (which is about the same size as the dog). Ha! The entertainment never stops...do your fur-babies ever do HILARIOUS things?
Picture: John Knox the Hot-Mess.