Tied for first spot: the saree I eventually wore to my wedding (I wanted white and could not find one, bought the silver and blue with the fairytale motif as backup. Corny I know) and a long, full gathered maxi skirt in teal printed with gold that was part of my trousseau and intended as back-up wedding reception outfit (the occasion did not present itself). Both felt wonderful and were serendipitous finds in my favourite colours, both in aesthetic and connotative terms. Both are very me and very affirmative outside the context of marriage too. They just are perfect-for-me garments though I will possibly never fit the skirt again and certainly never the choli blouse to match the saree.
close seconds: ancient zippered oxfords and new knee-high boots. Oddly both black, a colour I have a love-hate relationship with. They feel empowering. Make me walk taller and stridier.
I am also very fond of the pearly grey magnetite earrings SO got me from down under. Tickles the scientist part of me, especially when it is mistaken for pearls. And has a weird nostalgia value... I have fond memories of sailing in a ship laden with a cargo of iron ore.