Shorts for Winter

We've all seen it by now, this fashion trend involving boots, tights and shorts and quite frankly I don't know what to make of it. When I first witnessed shorts and boots it was much warmer and I wasn't too crazy about it. I couldn't help but be reminded of *gasp* hooker attire.
And have you experienced Montreal summers?! Boots would be suicide!
So I steered clear of this fashion trend...then came the promise of cooler temperatures and the shorts/boots trend stuck, only this time it came with tights in the mix.

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Ooooh! suddenly I love it! I still think it's a risky outfit. Get shorts that are a modicum too tight and you're back to hooker attire; wear the wrong top and...well, you know...hooker attire. But done right, I absolutely love this look! Take a look at Betty of Le Blog de Betty fame and Tokyobanhbao of Le Monde de Tokyobanhbao. These girls always seem to get it right! Now all I need is the courage to try this look out for myself and the weather conditions to wear my leather boots without ruining them.

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Evidently, it's a trend that many people dislike and there's a lot that can go wrong.

For example (imho):

...but alas, that is the ever-constant challenge with fashion trends, isn't it?