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Menswear Inspired

Menswear inspired clothing a la Annie Hall or Katherine Hepburn style has been popular for some time now.  But for those who haven't been ready to try it yet, I am going to give you a couple of tips and choices on how to pull it off!  If you're afraid of coming off as dressing "too manly", have no fear, many of the styles are downplayed, delicate and more romantic looking than you may think.  
Menswear for females started in 1966 when Yves Saint Laurent created the first women's tuxedo, 'Le Smoking Suit'.  It was created for women who wanted to wear something besides evening gowns and other dresses.  It was first made with black trousers and jacket with four button down pockets and a white organdy blouse.  Now at YSL every season, 'Le Smoking Suit' is revamped and modernized.






                                                                                                     Photograph by Helmut Lang in 1975

First, start with a blazer.  Pairing a blazer with jeans, leggings or slouchy pants is a trendy way to get a menswear inspired look. I like a slouchy boyfriend style 
For Fall 2010, Helmut Lang came out with this black boyfriend blazer

Kate Bosworth in a nude boyfriend blazer.  Wearing blazers in neutrals and more pale colors keeps the look more feminine

Rachel Bilson wears a blue sequined blazer which adds some fun to an outfit

Boyfriend jeans are also a great way to keep up with the menswear trend.  Everyone remembers when Katie Holmes started walking around in baggy jeans with button down shirts first.  Hers were a little too baggy and may not look flattering on everyone, but there are now better fitting styles that can flatter all figures.  

Boyfriend jeans at the D&G Spring 2010 fashion show

Victoria Beckham wearing boyfriend jeans and a black blazer

Jennifer Aniston wearing a more fitted pair of boyfriend jeans

Oxford shoes are a another cute and comfy way to follow the trend.  They are inspired by a mens dress shoe and have a perforated pattern called the 'wing tip' .  You can get them in one or two tone colors.  

White oxford shoes at the Spring 2010 Alberta Ferretti show

White Michael Kors oxford brogues

Whitney Port in two-tone oxfords and ripped boyfriend jeans

Sienna Miller making oxfords look super feminine with a short, ruffled skirt

More mens inspired pants: trousers, pleated and wide leg

Dries van Doten Fall 2010 trouser pants
High waisted pleated pants by Chloe for Fall 2010

L.A.M.B Fall 2010

Olivia Palermo in a menswear inspired look (note:briefcase bag as well)

Ashley Olsen menswear inspired, including square glasses

Other clothing items to think about: slouchy cardigans, tuxedo jackets, vests, fedoras (although they were originally made for women first in the late 1800's), high-heeled oxfords, oxford shirts