Try on a pair of au courant sunglasses at PorConceito: the ocular boutique opened in 2009 in the Bairro Alto district and offers fashionable frames reminiscent of Chanel and Dior for a mere $150. Next, redecorate your apartment with antique maps of the Iberian Peninsula, dramatic vintage fado posters and urbane fin de siècle magazine covers from Loja das Gravuras (Rua da Misericórdia 88, 213-423-261).
In Chiado, rediscover nearly extinct brands at A Vida Portuguesa, like Oprah's favorite all-natural Claus Porto soap or whimsical Bordalo Pinheiro plates. Treat yourself to a proper pair of gloves at the tiny Luvaria Ulisses, open since 1925. Get your hands massaged and measured, then choose a pair (or, at $88, two!) among a selection of fine-leather styles.
Return to the present along the waterfront esplanade across from Santa Apolónia train station. Find mid-century furniture at the design store Loja Datalaia, or fill out your record collection at the revered Flur. Get a high-end snack of foie gras and top-notch Quinta do Portal wine at sleek food emporium DeliDelux, or cap the afternoon along the Tagus River with a cocktail at the John Malkovich–owned boîte Bica do Sapato.