Not crazy about the phrase “ultimate personalization tool,” but I strongly agree that associates (F2F and/or accessible via any device) can be a true differentiating factor — for help, for advice, for relationship-building (extending), and yes, to sell (in the Dan Pink manner of selling).
Are retailers investing enough? No. A few are changing (Walmart and Best Buy come to mind), but it’s not pervasive.
It's too early to determine if this is a broadly adopted trend, but it's definitely an attractive proposition for a slice of the population. I can corroborate the Washington Post story with what an RTR store manager told me, that there are many customers who come into the store three times a week, and a few that have multiple subscriptions, essentially replacing their entire wardrobe.
Personally, I see it taking hold more broadly in handbags and accessories than ready-to-wear. But even in this scenario, the implications of an "owned wardrobe" focused on core items, surrounded by "BaaS" (Bling-as-a-Service) are massive. That's a lot of spend (and a lot of margin dollars) potentially shifting away from retail. I would also note the importance of the RTR "store" as a piece of the equation, especially in densely-populated urban areas.
This is not a simple either-or issue, and really needs to be discussed at the category level, not in aggregate. Thinking specifically about Enjoy, they are going after an opportunity abdicated by traditional retailers who lost their focus on customer service / experience / relationship. (Not dissimilar to Crutchfield back in the day). And they may be able to carve out a meaningful niche business. Who cares if they become the predominant way of shopping for consumer electronics. I bet they don't. All Enjoy needs is to be big enough to afford their infrastructure on a market-by-market basis. And without the cost of stores, there's a lot more to spend on a different type of infrastructure.
Switching to department stores, and apparel and softgoods in general, I think that Jerry Storch is right in many aspects. Digital will be involved in almost all shopping / buying activities, the vast majority of which will continue to include a store at some point in the process. The challenge, though, is cost structure. In specialty apparel, it only takes a sales decline of 10-20% to wipe out store four-wall profits. And combined with the investments required to build out Ecom, Mobile, Social, Omni-channel, etc, many retail chains are struggling to make the math work. And yes, some will likely go away.