Anna Wintour, the notoriously scathing editor-in-chief of Vogue magazine, has maintained the same sleek-bob-with-large-sunglasses look since she began her powerful role in 1998. What is most surprising to me is that the most powerful woman in fashion, instead of going with trends and experimenting with new looks, has embraced the timelessness of her one signature style, rendering her strikingly recognizable. The design behind this bob + sunglasses look is actually quite calculated. The sunglasses, large enough to cover her eyebrows and dark enough to omit any possible eye contact, are her tool to hide her reactions and thoughts while sitting front-row at fashion week runway shows. The woman behind every choice in every Vogue issue decides to keep her thoughts private, and unleash them to the world with every new print of the magazine. This element of mystery maintained by her particular style choices possibly renders Vogue magazine much more appealing, as what is held within its pages is an unpredictable surprise; a burst of excitement in the fashion world. As for her signature hair, The Telegraph UK named the Anna Wintour bob “the red carpet hair trend” of the 2016 met gala. Wintour’s bob is meant to embrace timelessness, as a simple yet classic and clean hairstyle to be worn at any age, which always exerts a sense of professionalism and seriousness. Rumor has it the powerful Wintour is so attached to her hair that she refuses to start any work day until it is blown out and styled to perfection. If there’s anything we can learn of Anna Wintour’s design, it’s that timelessness is almost as powerful as ever-changing fashion fads, and that one’s identity can be so closely tied to the way in which they stylistically present themselves (hairstyles, accessories and all), to the world.