I've seen these photos pop up on tumblr every so often and after catching a glimpse of her at Fashion Week looking so prim and proper, I'm sort of nostalgic for this version of her. I believe the pictures were taken right about the time she became editor-in-chief at Vogue in 1988 and I love how completely polar opposite her style was compared to today. She seemed to follow trends in her personal style much more back then, evident by so much color and texture. She plays it pretty safe (or classic to some) now, but I miss scandalously braless, sheer, colorful, sweatshirt wearing Anna! I can only assume Anna of today would never wear (or not wear) any of these things. I admire her commitment to a certain kind of look (same haircut!), which she's grown into over the years, but honestly I never got too into her current style or American Vogue for that matter. It lacks the pizazz I love. In the Vogue world, I much prefer someone like Anna Dello Russo, editor-at-large of Vogue Japan, who has no fear when it comes to off-the-wall fashion. To me, fashion should be fun and a part of self-expression, but Anna's choices today are definitely more uniformic than expressionistic. Do you think people grow into a certain kind of style as they age and stick to what works or are some just giving up on style as self-expression? I wonder what the ladies of Advanced Style would have to say about that. There's definitely some self-expression there! 

When I googled "young Anna Wintour" this picture also came up. Stylistically, if I had to choose between this probably early 70's look, the late 80's/early 90's looks above, or the classic Anna of today, I might actually go with this 70's version.  I love the hair and styling of her accessories with a such a basic sweater. It's such a clean cut look that I could see it on any girl then or now.

Here's some photos of today's Anna Wintour.

These are such clean looks, almost reminiscent of her young self in their simplicity so maybe..just maybe..her true looks of self-expression just happen to be this simple and her colorful looks of the 90's equate to a fabulous bump in the road to personal style.

[Photos: Cupcake Junky/Huffington Post/Shefinds/Haute Living]

Tagged in: anna wintour, Anna Dello Russo, Advanced Style, 1990s   

The opinions expressed on the BUST blog are those of the authors themselves and do not necessarily reflect the position of BUST Magazine or its staff.


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