On the morning of June 25, mega-fashion influencer Arielle Charnas, who's collected more than 1.2 million followers on Instagram and has her own clothing line Something Navy at Nordstrom, announced when Amazon's Prime Day would be kicking off this year. It was a not-so-subtle signal about what Amazon hopes to accomplish with its annual deals extravaganza this year. It still wants to be a bigger name in fashion.

When you think of Prime Day, you might be thinking about deals on Instant Pots and Amazon Echo devices — not half-off dresses and designer heels. But the market for apparel and accessories globally is worth more than $1 trillion, so Amazon clearly sees there's a lot at stake here. It's using Prime Day to tout fashion deals. And it's also had a slew of recent initiatives and tie-ups with fashion influencers — beyond Charnas — to show it's trying to establish the site as a place to shop for more than just the basics. It hopes to take market share as other apparel retailers are struggling. And it hasn't been afraid to experiment. Typically, when it comes to selling clothes, Amazon is really good at "the boring stuff," Wells Fargo retail analyst Ike Boruchow said. Wells Fargo has estimated that Amazon generated roughly $35 billion in sales in 2018 related to apparel and footwear, out of $232.9 billion in sales overall. For context, athletic apparel retailer Lululemon brought in $3.3 billion in sales last year, while Gap Inc.'s net sales were $16.6 billion, and Costco has said it generated $7 billion in sales in 2018 from clothes and footwear. Amazon dwarfs them all, even combined. But a lot of those transactions for Amazon stem from "commoditized" clothing items like white T-shirts, jeans and underwear, according to Boruchow. Amazon's in-house brand, AmazonEssentials, is popular for that sort of thing — selling a four-pack of women's camisoles for $24.50, or a 10-pack of cotton crew socks for kids for $9.45.

Bezos' vision for fashion

Amazon CEO Jeff Bezos frequently told colleagues in the early 2000s: "In order to be a two-hundred-billion-dollar company, we've got to learn how to sell clothes and food," according to the book profiling Amazon's ascent, written by Brad Stone, called "The Everything Store: Jeff Bezos and the Age of Amazon." At that time, Bezos set his benchmark based on the size of Walmart's sales, Stone said. Amazon surpassed $200 billion in annual sales for the first time in 2018. That figure includes revenues from its other businesses like Amazon Web Services, not just retail. Meanwhile, Walmart's total revenue was $514.4 billion for its latest fiscal year. Amazon is trying to sell more fashionable clothes today as mall-based apparel retailers like Victoria's Secret, Chico's, Dressbarn-owner Ascena Retail Group and Forever 21 are closing stores and struggling to draw-in shoppers. And department store chains like J.C. Penney and Macy's, which have historically been reliant on their apparel businesses to drive sales growth, are shrinking. It's been estimated retail store closure announcements could reach 12,000 this year, setting a record, with many of those stemming from apparel-based businesses like Charming Charlie and Charlotte Russe. This Prime Day, which kicked off Monday at 3 a.m. ET and runs for 48 hours, will put Amazon's latest efforts to be a bigger fashion destination to the test.

Lessons from Prime Day

Prime Day 2019 will include hot deals on staple items, like sweatshirts and socks, but also is promoting Amazon's own fashionable items to highlight the range of clothing it offers. Ahead of Prime Day this year, Amazon was pushing deals for as much as 50% off leggings, accessories and more, Jacquelyn Cooley at analytical intelligence company 1010data said. Fashion items very well could be on the top sellers list this year, considering how the deals are panning out, she said.

On Prime Day, Amazon is touting 30% off Calvin Klein and deals on some of its own exclusive apparel merchandise.

On Monday morning, button-down shirts from Amazon's Goodthreads line were 30% off, its own Lark & Ro dresses were 50% off, and certain Calvin Klein and Adidas merchandise was 30% off. Charnas took to social media again to tout her #PrimeDayPicks, including items from Amazon Essentials, Splendid and Rebecca Taylor. Overall, this year's Prime Day could bring in as much as $5.8 billion in sales globally, up from an estimated $3.9 billion in sales in 2018, when the event ran for just 36 hours, according to Coresight Research.

Beyond Prime Day

But a fashion business isn't built on a two-day sales event. Amazon has seemingly been amassing an army of fashion influencers on social platforms like Instagram, bringing with them tens of millions of followers altogether, to write posts with taglines like "I #FoundItOnAmazon." Women including Paola Alberdi, Sierra Furtado, Emi Suzuki, Leonie Hanne and Patricia Bright each have more than 1 million followers on Instagram. Now, they all share something else in common. They're working with Amazon to promote the platform as a fashion destination — alongside their posts about Reformation, Revolve, Channel, Rebecca Minkoff, and other trendy and luxury labels. One of Amazon's new influencer-focused ventures called "The Drop" went live in May.

With The Drop, Amazon is partnering with fashion influencers like Bright, a U.K.-based vlogger known for posting chic looks and night-out outfits to her Instagram, and Furtado, an LA-based YouTuber known for her more laid-back style. These partners are designing limited-edition apparel and accessories collections that Amazon will then create in-house. There's a scarcity element involved because shoppers are only given 30 hours to shop each influencer's collection before the next one is dropped. A text alert notifies shoppers when a drop is happening. Amazon also says on its website it only makes limited quantities of each drop, so products are expected to sell out. The Drop sounds a lot like fast-fashion retailer Zara's strategy, which has found success by never making the same thing twice, only shipping limited quantities of items to stores, and rotating inventory frequently to keep shoppers coming back again and again to flip through racks of clothes. Amazon appears to be taking its own stab at this approach.

In order to be a two-hundred-billion-dollar company, we've got to learn how to sell clothes and food. Jeff Bezos Amazon CEO

Amazon also has its own subscription box program akin to Stitch Fix called Prime Wardrobe, where users can pick out a handful of clothing items, try them on at home and then only pay for what they want to keep, shipping back what they don't want. And just last month it launched an artificial intelligence tool called "StyleSnap." Within Amazon's app, users can either take a photo or upload an existing image of an outfit, and StyleSnap will use machine learning to "match the look" with clothes for sale on Amazon.

Making shopping fun

Still, analysts and fashion experts agree that navigating Amazon's website for clothes often is more arduous than it is enjoyable. The website's design isn't desirable for discovering new things or new brands. Most people shopping on Amazon go there knowing exactly what they're looking for. With fashion, Amazon must figure out how to make the experience more fun. There's also reluctance for brands to partner with Amazon because they lose autonomy over pricing and marketing, founders have told CNBC. On the whole, it hasn't been easy for Amazon to entice popular fashion brands to sell there. The majority of product listings on Amazon's fashion page are from third parties. This is likely one of the reasons why Amazon has been incubating so many of its own apparel and accessories lines in-house. It has more than 60 today, according to tracking by TJI Research, like Core 10 for women's leggings and sports bras, and Goodthreads for men's khaki pants and button-down tops.

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