My suggestions: For upscale shopping, you can't beat the Golden Triangle/Montenpo area, which is basically via Montenapoleone, and it's parallel road via della Spiga, plus the crossroad via Gesu and also via Verri. You'll find Zegna, Brioni, Tincati et al. there. Via Manzoni which borders the Montapo area (if you are in front of La Scala, the road going to the left is Manzoni) is not too bad a place to shop too. There is a B. Magli store there on the right, and just behind it is the outlet.. The shoes that are carried are not just the thin slip ons, but the chunkier oxford/derby types, also some leather clothes (e.g, my wife picked up a nubuck pants for about Euro 60). Other nice menswear stores is Eddy Monetti (good quality RTW/MTM suits) on Piazza san Babila, Milan Store (for your fix of Incotex and Loro Piana pants) which is near Monetti. For outlets, there is of course Etro, plus Il Salvagente (Via Fratelli Bronzetti 16), Vestistock (viale Romagna), El Dorado (via Montenapoleone 26). Also the area around the main train station is a good outlet area (ingrosso). Remember that most of these outlets are more "fashionable" clothes, not the classic Kiton/Brioni/Attolini styles. I agree with Carlo, the Saturday/Tuesday market on the Viale Papiniano is great (make sure you end up towards the clothing area, not towards the kitchen,etc area). Selections are varied and yes you can luck out on Kiton/Brioni/Borrelli/Zegna etc. Just make very sure you know the real thing from a fake. Como is great for silks and the silk outlets: Mantero, Ratti, Seterie Moretti. At Ratti (it is on via cernobbio, check the phone books) you can get excellent ties for about Euro 25 upwards (e.g Escada 7 folds for about Euro 50 on sale).