Trends on Trial: Menswear as Womenswear

molly and colleen hurford return with a new trends on trial this time looking at the return of menswear as womenswear, a popular trend made famous by Diane Keaton in Annie Hall (as pictured in the header) … and in an interesting twist, molly models the trends that are on trial …

From shopping in the little boy’s section at Walmart to rocking men’s suit jackets from thrift shops to raiding my grandfather’s closet for his military fatigues and coats when I was 12, I’ve always been fascinated by menswear. And thankfully, it seems to be the style of the moment, whether the wearer is going for a casual look or a more sophisticated one.

Remember a few years ago when all fashionable guys from their mid-teens to their early 20s were wearing girl’s pants and we all wondered if they could get any tighter? (Turned out, they could.) Well, now the reverse is very much in fashion. You have to love menswear, since it is both charming and comfortable. So, in thinking about menswear, we started to think about all the men that we consider to be style icons and the ones that make us want to dress like them despite our collective lack of penis.

The first person to come to mind for us was Russell Brand. Whether you love or hate his comedy, you can’t deny that the man has style. We all saw him doing the opening monologue on Saturday Night Live recently, where he assured us that his absurdly tight pants are OK because he is much more famous in England. Sure, he is most well known for his offbeat comedy, tight pants and marriage to Katy Perry, but his whole sense of style is impressive. Maybe we’re drawn to it because we all have an affinity for wearing our shirts a little more open than what is technically considered appropriate. Also, his taste in shoes is beyond that of any normal man — they are always pointy and classy while still matching his wacky personality. (We especially like the pair of ankle boots that are pointy and leopard print.)

Another man in the spotlight and undeniably fashionable is — bear with us — Steven Tyler. We admit to watching American Idol this season just to see what the Aerosmith frontman is wearing. You have to love a man with an affinity for animal prints leather, and gorgeous long hair. Seriously, if we could raid that man’s closet, we would not hesitate. Even his accessories are great. He always adds flare with jewelry and scarves that would be the envy of any woman around. What is it about aging rock stars that makes them dress better than everyone else? Maybe it’s that they never seem to leave behind the style that made them famous. Tyler is just as fashionable today as he was when he was constantly strutting around the stage.

But why is menswear suddenly en vogue? Maybe women got tired of strutting their stuff in over the top lacy numbers. But more likely, it’s because: A. it’s comfortable, and B. it’s classic. Menswear on women never truly goes out of style — rather, it fades into the background for a few years at a time, then blasts into the forefront when designers need a fallback. Additionally, it looks bangin’, and frankly, is one of the easiest trends to get on board with, as long as you have access to a boyfriend, spouse or thrift shop.

Some of the best trends include:

The Business Suit: re-tailored, this isn’t the neon pink powersuit of the ’80s. This is the high fashion wide-legged trouser with fitted blazer version of the classic tailored men’s suit, and while it may seem more suited for the runway as opposed to something a normal woman can pull off, it’s actually easily adaptable. A wide legged — but not too wide — trouser with heels and a casual silk shell with a fitted blazer on top can work on pretty much any figure.

The “Boyfriend” Jean: we can’t get enough of the cuffed jeans that are worn loosely at roughly Capri length, ride low, and can even — if you’re feeling daring — show a bit of boy brief underwear if you’re wearing a cropped T-shirt.

Men’s Shirts: from large scale button-downs to a “borrowed” sweater from the boyfriend to an oversized flannel, when worn with skinny jeans or leggings, the baggy shirt offers great opportunities for layering and creates a super easy deconstructed look.

The one thing we’ve noticed about making menswear wearable without giving up femininity seems to be that while one piece can be sized up (wide-legged pants, slouchy boyfriend jeans, large flannel top), it needs to be balanced by something with a slimmer fit.

Of course, we haven’t forgotten accessories! This is perhaps the most practical — and fun — application of menswear, and we’re absolutely in love with it.

The Briefcase/Messenger Bag: purse just won’t cut it? Trade it in by shopping at TJ Maxx for a men’s briefcase or messenger bag. It adds a masculine edge to an outfit while adding more storage space, better laptop-toting options, and a crisper look overall.

The Fedora: channel your inner Blues Brother with an awesome fedora, possibly rocked with sunglasses and an also incredibly hip skinny black tie

Suspenders: you might recall our reference to the “braces” worn by skinheads, but it doesn’t need to be a solely punk trend. Rather, it can be a great way to hold up those boyfriend jeans. And come on, who doesn’t want to look like Erkel?

Men’s Watch: these huge clockfaces may seem bulky at first, but they grow on you when you realize how much easier it is to check the time. Wear with a sweater with the sleeves rolled up for instant geek chic.

Men’s Hats and Scarves: so much cheaper and so much warmer than women’s scarves, and with a peacoat, can work wonders towards creating a military-inspired look.

So strut your stuff in some sweet menswear — this is one look that’s practical, inexpensive, comfortable and whimsical, while still being work-appropriate. Seriously, what are you waiting for? This is one trend that we wholeheartedly approve of.

Case dismissed.

Founded in September 2009, The Pop Break is a digital pop culture magazine that covers film, music, television, video games, books and comics books and professional wrestling.