I live in the city now (EV). I like boutiques better than malls where I get totally overwhelmed. Like at Forever 21, if it's not in the window, forget it. It's too noisy inside. Boutiques (except for a big concept store like TW&C) usually have decent mid-season sales because the owners need the cash for new inventory. So I wander about, go slow. I usually look for lines that fit like the top brands. The clothes I find always get noticed, too, because nothing is cookie cutter.
Tony Walker & Co is in the Tony Walker Center, right on Main Street, near the Main Street East exit off the 290 in the Williamsville suburb - before driving gets too strip mall insane. The store has lots of assistants, but if you tell them you just want to look around and try stuff on to get familiar with the brands, they won't pressure you. They are totally instructed to serve, but they'll back off if they understand you are just in to sample. They have a brand new guy shop that is connected through the back of the shop, so if you want to go with a boy, he can look at his own stuff. Lots of funky t's to go with jeans.
If you head into the EV in downtown, then you want to walk Elmwood Ave between W. Ferry and Lafayette, that's where there is the greatest concentration of stores, including Urban Threads for jeans (small but good, high priced selection). You can almost always find a place to park on Elmwood just south of W. Ferry, then head north. There are other places north and south of that patch, also on Elmwood. I'm just telling you the thickest part. There's always people out with dogs, at the coffee houses, just walking, students from the Universities and professional types. The storefronts can look a little tired, but they are really well stocked. The EV just got voted one of the top 10 neighborhoods in the country by some neighborhood association. It's really cool to walk around the holidays when all the lights come on. I sound like a rah rah, but I'm just trying to let you know that it is safe and so not a waste of time.
Where do you go?