Good question Shop!
I have a wardrobe full of tat bargains and nothing that close to my heart. This is a problem, I think.
If jewellery is allowed, I would take a necklace and earrings which belonged to my gran, which I wore on my wedding day. By the time I'd rifled through my jewellery to find them, I would just have time to grab my All Saints leather jacket on the way out. It was a gilet when I bought it, and I had leather sleeves added to make it into a jacket.
If I don't take the jewellery, would take Nike x Liberty hi tops and barbour with liberty lining!
Now a question from me: what are your "ones that got away"? Things you didn't buy then regretted or gave away in a fit of decluttering and regretted?
Mine are a whistles scarf with pineapples on it, waiting for it to go on sale and it sold out. And a bag whose strap broke so I got rid of it, but without strap it would have actually made a really good clutch and I see a lot of them about and feel irritated.
I can't remember who linked to the Whistles shoe but they are on sale at the moment. here.