Ask Alison: How To Wear Those Pants Your Friends Hate

Sometimes you should listen to your friend's advice about how something looks on you. But mostly, you should just follow your heart.

Apr 3, 2013 at 10:00am | Leave a comment

I love getting emails from you guys. You are a bunch of smart, clever, interesting babes. I especially love it when you send me your fashion conundrums. Here's a recent email I received:

"Hi Alison,

I have been loving your articles on xoJane. I love your approach to fashion, so I am reaching out for some help. On a whim of fashion (something that doesn't often happen to me) I fell in love with, and purchased, a pair of gray ankle length pants [Lauren Conrad for Kohl's]. They make me feel strong and confident, like Katharine Hepburn.

I love them and see so much potential but haven't been able to get myself to wear them out of the house. My friends hate them, and keep telling me they just don't work on me.

Based on the 'guidelines' I've read online, I should be able to rock them since I have long legs relative to my overall frame. However, I am 5'4" and have broad shoulders and big boobs. Please, help me figure how to style these pants so I can prove my friends wrong!"

-Elissa

What are friends for, if not to tell you when you can't pull something off? But there are also times when you should ignore what people tell you and just follow your heart. The fact that Elissa mentions these pants make her "feel strong and confident, like Katharine Hepburn" is reason enough to persevere and figure out how to wear them. Here are the pants in question:

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Wait what? These are adorable pants. 

I'm unclear as to why Elissa's friends keep telling her they don't work on her.

1) It's sorta mean.

2) It just isn't true.

I think the slim cut yet relaxed silhouette is one of the most flattering things a girl can wear! The reason Elissa feels like Hepburn in these pants is because they are so very late 1930's/early 1940's, when menswear for women was really pushing the boundaries of what was "acceptable" for women to wear at the time. Can you believe the simple act of wearing pants was once considered "fashion forward"?!

And now for what to wear with them -- Elissa has a great foundation with her black lace-up heeled oxfords. I think a pant that has pleating around the hips needs a sleek, skinny finish via a slender heel. Also, the colors she can wear with said pants are endless, as they are the perfect shade of dark charcoal grey. 

Elissa mentioned she has broad shoulders and big boobs, which I think actually lend themselves to a 1940s inspired outfit perfectly. Women of the 40s were forever adding shoulder pads to their blouses to get that square shouldered look Elissa has naturally!

We have an actress on our show with broad-ish shoulders, and I put her in a ton of off-the-shoulder and dolman tops. (Dolman is just a fancy word for bat wing sleeves.) A proper dolman sleeve has a deep armhole that tapers as it nears your wrist, thereby fooling the eye into thinking it's the cut of the shirt that is broad, not your shoulders. They are like MC Hammer pants, but for your arms.

Some women with bigger boobs find button front shirts hard to wear, as the buttons are forever popping open. A shirt with a more generous sleeve cut allows for a little extra room in that area. 

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Draped neck top, $55.00.

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Draped hem blouse, $836.00.

A top with some inventive draping is a great way to feminize a pair of menswear style pants. I like the way this turquoise top gathers itself at the waist, and I always think a slightly blouson top helps the proportion of a skinny-ankled pant tenfold. 

(You will notice that some of the pieces I've shown and linked here are $$$$ -- but the point is to use them as a guide when you are shopping for similar styles in real life!)

I think the key to Elissa wearing her pants successfully may be to find a top that isn't too voluminous at the bottom, and that looks good tucked in/finished with a belt. A short sleeved top with a wide set dolman sleeve achieves this nicely -- and a contemporary pattern takes away any stuffy "period costume" look her pants may have, as that may be what her friends are responding to with their distaste for them.

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Embroidered top, $645.00.


I love the combo of super bright hot pink with charcoal grey. Hot hot hotter than hell hot pink is an easy, instant way to brighten your face and draw the eye upwards to that same cute face.

This acid-bright color theory works with hot orange too:

The cuffed sleeve and exposed zipper would give Elissa's tailored pants a nonchalant vibe that would be right at home at the trendiest of trendy NYC cocktail parties. 

Happy pants wearing, Elissa! Tell your friends to read this and weep. 

Big XO,

Alison