AllyG: You know who I’m really getting into lately? Serena Ryder. I love her for more than her indie cool. Her music is what my friend Iain calls, “drinking in the dark music”. Have you ever been there? Her songs remind me of the period of time I lived alone on Argyle St. atop of the Bitter End. It was a particularly intense growing period, also known as an incredibly self-indulgent phase. Blah, blah it made me who I am today. Anyhoo, back on Argyle, I would slide into my studio apt (much sexier than referring to it as a bachelor pad) and pour myself a glass of wine, turning on some Sheryl Crow (ironically, I believe it was Sheryl’s self-indulgent phase as well…If it makes you happpppppppyyyyy…..) and staring out the window and the crowds rushing by eager to start their weekend. Serena’s music reminds me of that. Not sure why. Perhaps it’s the ache her music leaves you with, her lyrics remind you to remind yourself of who you are. Does that make sense? Anyways, this is a fashion blog, not All About Ally (which is an AWESOME name for a blog). So! Serena!

I wish every single day to be this effortlessly cool. The suit, the hair, it’s working.

This is Serena with one of those “umbrella” things that L-A is always going on about (seriously, I will not acknowledge the rain. The more you acknowledge it the more it wants your attention, and no, this is not going to be my parenting style). She’s also carrying a Starbucks. See? Something for both of us!

Here’s Serena performing Sing, Sing, Sing at the Highline Ballroom in New York. Ridiculous, non?

And my current fave, Little Bit of Red…

I think we all know that I love my pop music (as well as Country with a capital “C”). So I’m also quite into Lights, although I confess that I can only really identify one song of hers, “Drive My Soul”

I find it interesting that her manager is Jian Ghomeshi, the very same man who made International headlines (in the entertainment sections at least) for successfully outing Billy Bob Thornton as an asshole. Although, I don’t really think that was a Mount Everest league challenge. Dude, Billy Bob left his then-girlfriend, Lauran Dern for Angelina Jolie while she was off shooting a movie. Laura dished, “”I left home to work on a movie, and while I was away, my boyfriend got married, and I’ve never heard from him again.”

That’s an asshole move!  I love this quote from Eye Weeky dot com, “Astronaut-escorted Lights trades blazing smiles with Ben Mulroney while her manager Jian Ghomeshi smugly looks on.” It may be the most apt description of all three individuals I have yet to read. Not sure what she’s like as a person, but I do dig her style. She’s young, and she’s expressing herself well. Seems like she has a flair for the creative as Flare magazine reports she often wears her own graphic tee designs, which is pretty cool.

I could never work the 70’s headband style, but I’m also not in my early 20s. Lights does it well. If I could I would cut her hair off and glue it on my head. I think I’ve said that before about someone else. Whatever.

I also really adore her yellow dress she wears in the Drive my Soul video, particularly matched with the golden boots. Not everyone can pull it off, she can.        L-A will correctly point out that she looks like she shops at American Apparel. The Flare article confirms this fact. We all know where I stand on AA. Love it.

$20 bucks says L-A will talk about an artist I’ve never heard of. She also enlightens me like that. Just like when I share my Britney Spears music with her. Aren’t friends awesome?

L-A: Ally, remember that time I sent you a postcard and addressed it “Ally, Above the Bitter End, Argyle Street, Halifax” and it still made it to you? Good times.

Anyway, we all know where I stand on AA: mostly hates it.  So we’ll save that rant for another day.

I would introduce you to music you’ve never heard of, except that: (a) I actually suck at music/discovering music. I am serious when I say that if CBC Radio one doesn’t play it, then I won’t know it. And I don’t listen to that Q show hosted by Lights’ manager because I really dislike He-Who-Shall-Not-Be-Named (although, that label could easily be applied to the youngest Mulroney).  (b) I will admit that most musicians I like are not known for their sense of style. Probably because they are Too Busy Being Artistes or Serious Musicians or something like that to worry about style. (not really an excuse).  and (c) I’m feeling lousy because of a cold and it’s best that I focus on just trying to type up a post rather than looking for music videos (and I apologize now for trying to blog while ill. From here on out, this post may or may not make sense).

I’m going to focus on that Serena Ryder kid. I don’t super dig her music, but she’s got an interesting sense of style happening. If you follow any style blogs or fashion mags, you’ll know that at least once a year someone will mention the boyfriend/menswear inspired look for ladies and they will, of course, reference Annie Hall:

Because how can you not? It put menswear-inspired style on the map. (It’s also an enjoyable movie. The Marshall McLuhan scene kills me everytime).  What I really dig is that this was apparently Just How Diane Keaton Dressed. There was a costumer on set and she worked with Ralph Lauren to perfect the look, but legend has it the costumer really didn’t dig the look.  I guess she feels really silly now. Or denies this story every chance she gets. Because clearly this movie was a Fashion Moment.  And Diane Keaton is still working that look to a certain extent:

Diane’s got some great gams. Because this is one of the few times when I can honestly say that leggings are working on a woman older than 30.   Anyway, she still has a slightly menswear-inspired look and it usually works. I’m not going to recommend that particular outfit that Diane is wearing. I could really do without the hat.

But I do like the menswear style and I’m pretty sure Serena Ryder does too. She is working that vest and shirt nicely in the second video. And vests/waistcoats are not easy to wear. You can end up looking like a raging idiot who is trying to be trendy or like someone’s grandfather if you’re not careful. And I guess that brings me to a point of sorts: the menswear look, like all “looks”, needs to be approached with caution. You can always take it too far. The trick may be to trying to keep it somewhat feminine. And to possibly be built like a model. For example, dujour’s roundup of Irina Lazareanu’s look:

Let’s lose the hat, but otherwise, Irina’s rocking her menswear. I really enjoy the second outfit, but I would look like a sack in it. So for me, the trick is to just wear one or two pieces of menswear with clothes that do not make me look like I’m wearing pants I’ve made out of a burlap sack. For example, I am not compeletely hating these shoes:

I particularly like how Net-a-Porter styled them with this Smythe boyfriend blazer and skinny jeans:

The blazer is cut so that it still looks like it’s made for a woman, despite it’s menswear styling (like Secret deodorant or something) and it’s paired with a blouse that is actually quite feminine and a great bag.

I’m using Net-a-Porter as an example of how to do things, so my links to things like the Church’s brogues are for those of you with a heftier shopping budget. But there is hope for those of us with a more meagre budget. Joe Fresh has an almost identical pair of shoes available in their stores right now:

Sure the quality won’t be there, but if you’re planning on jumping on and off a style bandwagon, it’s better to spend a fraction of the price (the Joe Fresh pair cost $60). And the excellent folks at WhoWhatWear have compiled some items that are all under $100.

So, some final thoughts: proceed with caution when working this look. Buy menswear-inspired (not actual menswear – unless you happen to be/know a particularly good tailor). Mix it up with some more feminine looking items.  And then go drink a bottle of wine while listening to your music in the dark. You will look very classy doing so.