By Sarah Begley
May 21, 2015

On May 18, clothing giant Ascena Retail Group said it would acquire Ann Taylor and Loft for $2.16 billion. CEO David Jaffe is expanding his collection of popular fashion brands, which already includes Dressbarn and Lane Bryant.

• HIS CLAIM TO FAME

Jaffe’s parents started Ascena with flagship brand Dressbarn in 1962. Both had retail backgrounds: he worked for Macy’s, she for Gimbels. Jaffe’s father didn’t want Jaffe to join the family business until he had 10 years’ experience elsewhere, so he got his start on Wall Street investing in retail giants Office Depot and Petco.

• HIS CURRENT CHALLENGE

Women’s apparel is at a crossroads: tastes are changing as casual clothing becomes widespread and consumers cut back on high-end purchases. In the past year, brands like Coldwater Creek, J. Jill and JCPenney have struggled. Jaffe will need to prove that his brands can transcend the trend.

• HIS BIGGEST CHAMPION

Wall Street. The deal makes Ascena one of the most dominant players in women’s clothing. Adding the stylish Ann Taylor to its portfolio brings a deep customer base of suburban working women.

• HIS BIGGEST OBSTACLE

Jaffe has to convince shoppers that it pays to invest in pricier clothing rather than in less expensive fast fashion like H&M. He will also have to confront a rising demand for activewear.

• CAN HE DO IT?

Jaffe may not have trendiness on his side, but he now has a reach into key everywoman demographics: women who want a deal (Dressbarn), those who want basic work wear (Ann Taylor and Loft) and those who need plus sizes (Lane Bryant).

–SARAH BEGLEY

Contact us at editors@time.com.

This appears in the June 01, 2015 issue of TIME.

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