Despite efforts to turn it around, Gap (NYSE:GPS) continues to struggle from year to year and quarter to quarter.

On this video segment, MarketFoolery host Chris Hill talks to analysts David Kretzmann and Aaron Bush to dissect the company's management style and choices that will influence the retailer's results this quarter and over the years.

A full transcript follows the video.

Chris Hill: The Gap does not report earning until Nov. 19, but the company warned that falling sales at the namesake store Gap, and Banana Republic are gonna cut into third-quarter profits. Stock's down today. That's a phrase you could use for most of 2015 because this has been a really bad year for the Gap. And, it does not appear to be getting and better.

David Kretzmann: No, and when you look, stretch that time horizon over the past year, the past five years and the past 10 years, the Gap has underperformed S&P 500. So it really hasn't been a great long-term run for the company. There have been different stretches where the company and stock have done OK or even outperformed.

But it's interesting. We had Arthur Peck join as CEO in February of this year and he previously headed up Gap. He was the president of Gap's growth innovation and digital segment. And I thought that was interesting. That's actually a category at a company. Gap could really use any of those three right now.

I mean when you look at Gap, you have to kind of look at long-term performance of the company and what management has done. Over the past five years, they've spent more than $8 billion buying back stocks. So, this company is still generating cash. A lot of that cash is just going to buying back stock. The diluted share count has dropped 50% since 2010. The stock has still underperformed since 2010. So, for me, I see that, how much money they're applying in the share buybacks, and the stock is still underperforming. I kind of question, isn't there a better way to return that capital to shareholders?

Either investing in your brands, which are very clearly struggling, or paying a dividend instead of buying back stock. There are a lot of different options for that cash. And Gap is still producing more than $1 billion in free cash flow, so there are still some things to like for the company, financially. But managements' decisions I'm really questioning.

Aaron Bush: Yeah, I agree with David on all of that. One other point, I would add, less about Gap specifically and more kind of a bigger picture thought. Which is that just in general, "cool" kills itself and I feel like we've already seen this story with Gap before.

But it's really just the idea that, if a company's advantage is literally just to be fashionable, or just to be cool. So, fashion just for the sake of fashion. That edge is just not going to hold. It never does. Because just once something is cool, everyone jumps on board. And in the fashion world, once everything is cool, it moves on. And so I think it's just kind of seeing that over and over again, as Gap with all of their different little brands underneath try to catch up. They're just right back to not being cool again.

Hill: And if you think back to when this company was at its strongest, it was in part because it had great leadership, it has very strong operations. Because any apparel retailer is going to have to deal with inventory, management, and all that sort of thing.

But also it has this really great pipeline that it set up. When you think about the life stages that a person goes through. They had Baby Gap, Gap, Old Navy, Banana Republic. And if you think about it, just someone who is a teenager, they're gonna shop at Old Navy or something like that. Then they get a little bit older, maybe they're shopping at Gap. They become a young professional, they're shopping at Banana Republic, more fashionable clothes. Then if they get married and have kids, they're shopping at Baby Gap.

And so, it really was set up. We can have customers not just for a five-year period. We can theoretically have customers for a 30- or 40-year period. But as you said, Aaron, the more that they double that, it really does seem like you go back 15 years or so. And they really were trying to double down on "cool" and fashion. As opposed to just being a reliable apparel retailer that you could get a decent value. I think that's at least part of where it started to go wrong for them.

Kretzmann: Yeah, I think you can kind of compare Gap, maybe Gap pre-2000 to a similar business model as Carter's, which provides baby apparel and apparel for toddlers. That's been a really reliable business for more than a century now. Fashion and retail are tricky enough business on their own, but when you combine those, it's really hard to have a sustainable advantage there. And we're seeing that with Gap, the company's really struggling.