When Jeffries became CEO in 1992, Abercrombie & Fitch had 36 stores that generated approximately $50 million in annual sales.

Jeffries saw an opportunity in teen retail, and today Abercrombie has grown to more than 1,000 stores, with annual sales surpassing $4.5 billion, according to its annual report.

The brand is now at a crossroads. Its heyday was during a resurgence in preppy fashion, and it's had a tough time figuring out how to embrace the new quirky, hipster style. Abercrombie has also struggled in Europe, where it was banking on major growth abercrombie.

The company must decide: Does it evolve to chase its aging consumers, or start targeting new, younger ones?