When I graduated from college, I joked that I was able to make the leap from Old Navy and Gap to Banana Republic (BR). Having a real job meant more grown up clothes, and BR seemed like the easiest route. I don't think I'm alone in this progression; after all, the reason that I started shopping at Banana was that most of my co-workers and friends did, too. The only problem is that Banana Republic is a weak brand, especially for men. It is, almost by definition, designed to help you blend in, not stand out. The very impetus behind the "upgrade" mentality that first brought me to shop there is the exact reason why I don't anymore.
As I've grown older, I've started to define my own personal style more distinctly. Thus, I gravitate toward brands that are themselves more clearly defined. Over the past several seasons, J. Crew has set themselves up as the pace setter for classy, accessible mens fashion. Their pieces are no more difficult to understand than BR's, but have infinitely more character. Their careful collaborations with other brands like Belstaff and Ray-Ban have helped to dispel the idea that a men's store should be a one-stop shop, where you dress head-to-toe in their clothes, accessories, underwear and shoes, while also bringing some obscure, high-quality brands into a bigger spotlight.
Meanwhile, walking into a Banana Republic today is much the same as it was when I first graduated from college: solid suits in a limited number of cuts, loud striped shirts, relaxed jeans, fat ties, and graphic tees. Their "modern fit" suits are anything but. Blah. Even the name seems disingenuous now: just like Abercrombie, what was once a globe-trotting outfitter brand has become the definition of mall crap. Are they supposed to be American, British, or European in their influence? Who knows! If you doubt that BR was once an interesting brand, do an eBay search for "vintage Banana Republic" and see what I mean.
Even corporate sibling Gap has started to regain a more distinct identity, focusing on core products like jeans and tees with a new commitment to fit (see their new t-shirts) and manufacture (selvedge denim). They've also brought in the most obvious outside brand (Converse All-Star) to go with their all-American identity. Far from vanilla, Gap is now crafting basics that really matter.
Meanwhile, Banana stands apart, trying to borrow cool with Mad Men promotions (when there's precisely nothing in the store that a character from that show would wear) and relying on repeat business. It's lazy and it's a losing strategy. The name Banana Republic should bring to mind travel, adventure and daring, but all it really means nowadays is "baggy gray suits". Bring back the linen and the safari jackets; make suits that you can travel the world in, cut for Milan not Milwaukee; make high-quality boots and don't redesign them every dang season, so that they become collectible classics; just be distinctive.
Guys will buy it. They already know the brand and they do trust you. Make that trust worth-while. Make it a real upgrade.