Winter Shorts | WhyDid.com

Why Did You Wear That: Now and Later (Later)

By Kirsten|September 5th, 2013|Personal Style, Why Did You Wear That?|

I love winter shorts, but this is yet another style gamble that you can lose the house on. When executed properly, the look is young, playful, and a great way to get more wear out of your favorite shorts. However, when you roll the dice and lose, the stares you’re going to get on the street won’t be those of admiration. They’ll be looks of horror, possibly pity, and most likely secondhand embarrassment. You know, the same look you had when you informed the girl seated at the table next to you that she had a toilet paper tail. Oh, that was just us? Anyway, many moons ago, I put together some winter shorts guidelines that still hold true to this day. So, go ahead and hold off on stashing your short shorts for just a little while longer.

hat: Urban Outfitters, t-shirt: American Apparel, sweater: Henri Bendel (similar here), shorts: c/o Cult of Individuality, tights: HUE, bag: Alexander Wang, boots: All Saints (similar here)

Later.

xx,

WhyDid

Photo Credit: Michael Stiegler

Why Did You Wear That: Did You NOT Get the Memo?

By Kirsten|February 19th, 2009|Celebrity Style, Why Did You Wear That?|

So apparently, not everyone got the memo about what kind of shorts are deemed “acceptable” as winter shorts. Walking around yesterday, I spotted not one, but THREE girls sporting cut off denim shorts and tights.

I get it, you love tights, you love cut off shorts… why not just wear them together?? Because it looks stupid. That’s why. I love tights and denim shorts myself, but not together. And I understand you’re feeling a little confused about this bipolar weather we’ve been experiencing in New York lately, but hold off on the cut-offs. It’s still only February.

Maybe some photos will help you reconsider your choice of mixing tights and Daisy Dukes: (more…)

Why Did You Wear That: A Short Story

By Kirsten|December 19th, 2008|Why Did You Wear That?|

It’s December, I live in New York, and I’m wearing shorts today. Seriously, I am. They are calling for 8 inches of snow by the end of tonight, but I don’t care. I’m wearing shorts. To me, this is actually not weird. Seems perfectly normal, but after seeing people FREAK out about Katie Holmes wearing shorts in the winter time, I figured it was time to address the issue.

So, here I go. Now, I can’t say that I can vouch for Katie’s outfit choice. I think she executed this look very poorly, but I give her credit for doing it. (I also realize that this is going to become a huge trend now that she’s done it— remember the cuffed jeans?)

Anyway, I see nothing wrong with wearing shorts in the winter as long as you do it correctly. Here are some simple guidelines:

The shorts should be winter shorts. The material should be heavier than shorts you would wear during the summer and they should be dark, unless you are doing winter white, then I’ll let it slide.
You HAVE to wear tights with them, duh. That’s the whole point. You’re wearing shorts, but it’s winter, remember? I recommend heavy opaque tights, patterned wool tights, or if you are doing an evening look, a sheer black tight with back seam for added drama.
For shoes: short booties, tall boots, oxfords, or a close toed heel. I do not recommend flat shoes for 95% of the population. Unless you have incredibly long or lean legs, flat shoes are going to be hard to pull off.
Your shorts shouldn’t be too tight or too short. That’s what the summer time is for.
An added bonus… wearing shorts in the winter will prevent you from packing on that extra holiday poundage. Thunder thighs need not apply.

Here are some looks that work: