Gender bender

On our way back to the office from a client meeting, one of my colleagues asked me:

"Sir Lester, since you always look like a walking lookbook, can you give me tips on how to shop and dress up so I look unique?"

It was a question that caught me unaware, primarily because I think of myself as plain, boring and unadventurous in terms of fashion. So, I don't think I belong in a lookbook, unless there's a "before and after" segment, and I'd be the "before."

But since she asked the question, and I'm obviously into shopping, I decided to give her a piece of advice that she probably doesn't hear a lot:

"When you go shopping, shop outside your gender."

As expected, she asked me what I meant when I said: "shop outside your gender." So, I explained to her that if she wants to look unique, she shouldn't limit herself to shopping in the women's section. After all, you can find equally interesting items in the men's section.

Here's a case in point:

I bought Ate Bullet this printed pair of pants from Express. The cut was skinny, and the print was almost leopard-like, rendered in red and black.

The moment I saw it, I knew that a plain black top would be the perfect foil for the pants. Also, the top should feel very relaxed and loose, since the pants are already very slim and structured. It called for a "boyfriend top," so I thought, buy something for the boys.

So, I bought this men's undershirt from Body Glove. It was made of very soft cotton, and had a nice slouch to it. The v-neck was higher than usual, and it frames the face well.

To give it a bit of a girly vibe, I just folded the sleeves. That gave it the right length and clipped a bit of the masculinity off of the shirt.

Putting those two pieces together resulted in this very Alexa Chung look which was laid-back yet chic.

And it's a look that's achieved because of thinking outside the clothes box and not limiting your choices to the women's department. 

Borrowing from the Boys

Ever since Katherine Hepburn and Diane Keaton made appearances wearing loose and baggy men's clothing, the concept of "borrowed from the boys" fashion became universally accepted. Soon enough, more and more women found themselves wearing apparel and accessories meant for guys.

That's why there has been a proliferation of "boyfriend" clothing. There's the boyfriend shirt, boyfriend jeans, boyfriend shorts, heck, there's even a boyfriend perfume. Likewise, women are wearing oxfords and brogues, and carrying satchels - items usually seen on Preppy Prep School boys.

Ate Bullet is a big "boyfriend" fan. In fact, she borrows things from me. One time, she ended up wearing my jeans, and she also wears my watch with the faux crocodile strap.

That's why when I saw some mannish items, I immediately thought of her and whipped up this look:

It started with this nice denim shirt that I saw in SM Department Store. It's made of light denim but with a dark wash. The fit is loose and comfortable, which is perfect for our unpredictable weather. 

Surplus Shop has these men's style khaki trousers, but cut very low to fit a woman. Ate has been in a khaki state of mind, and she's wearing out the khaki Forever 21 trousers I bought her before. She'll need another pair of trousers to go on rotation, and this fits the bill perfectly. And yes, they're cuffed, too.

The final touch? These cool "lolo shoes" from Primadonna. They're 50% brogues, 50% golf shoes and 100% cool! This is the perfect way to punctuate this "masculine" look.

Overall, this look is actually very, very tomboy chic. If Ate still had her long, wavy hair, she can go all Alexandra Chung on you.

As a testament to how masculine this combination is, I usually wear a denim shirt and khaki trousers to school. But no, I'm not into brogues and don't wear shoes of this style. Give me my Chuck Taylors and Jack Purcells anytime.

And I think it's the pair of shoes that separates the boys from the "boyfriend" girls.