I remember first coming to the Wrentham Village Outlets with pretty much all the women in my entire family (mom, 2 grandmoms, 5 aunts, etc.). Now that I'm older, I can see why they hauled in all these women on one trip - the outlets provide a crazy amount of sales you can't get in any mall or galleria. There's like 100 different stores, half that look like endless warehouse spaces. You definitely need to clear out a full day for this type of shopping event. Black Friday is a biggie for the die hard shoppers, I remember 2 years in a row driving down at 5am the day after Thanksgiving with some gal pals (but you seriously need to know what you want and be prepared to wait in a heinous line for it). Any other day is still pretty crazy, which I find pretty strange considering Wrentham is a ways away from Boston. But the set up of the stores is great, just one really long strip of stores with adequate outdoor walkways. Basically, in the end you want to make sure you're visiting these outlets to find something specific, because you don't want to waste a long drive and leave with nothing (gotta pre-check those sales, people!) - and I mean this for men and women, because there's much more than just typical apparel stores here, there's electronics, houseware, toys, and really almost anything else you can think of.
Pros: so many good outlet stores with great deals
Cons: really out of the way from the city