Practical advice for the impractical dresser

It’s no secret that Portlanders know how to dress for terrible weather conditions. We’ve got Patagonia and Pendleton to keep us from developing hypothermia, or at least what Portlanders believe to be unbearably cold weather.

It’s also no secret that I’m an impractical dresser.

On the recent December evening when Portland experienced stronger than normal winds, I found myself walking to work not in a protective, reflective jacket, but a tiny vintage jacket and tea-length tulle skirt. I looked like a stylish hybrid between Cinderella and a snowdrop, but tulle was flying everywhere and I was practically in danger of being knocked over by the wind.

For those of us who take pleasure in more intricate ensembles, winter is both our most preferred and detested season. On one hand, the opportunity to layer gives us a variety of possibilities for mixing textures and patterns, but that one pair of heels that goes with that one skirt doesn’t always help you survive the doings of nature.

I used to think that there was no way I would ever choose comfort over style. Personal expression was always more important to me than comfort, which would make me look and feel boring. The word practical was something I avoided at all costs within my vocabulary.

Yet as disappointing as I once thought it sounded, this season I’ve developed ways to save my personal style without constantly tending toward blisters and rips.

Have an extra pair of ballet flats in your bag

I used to hear this all the time, thinking it would never be me, but I’m glad I’ve jumped on this bandwagon. The women of Washington, D.C. have their priorities straight. I am an avid high-heel wearer and, like any shoes, they get worn out over time. I have learned this the hard way in many rain-soaked instances that nearly ruined some of my most treasured shoes.

Now if I need to walk long distances, I wear my flats on the road and switch into heels at my destination. This way I know I’m not harming a beautiful pair of shoes, and in most ways ballet flats paired with a more heels-oriented outfit is quite charming. I’d even dare to say how French this secret is, and American society eats that Parisian appeal up.

Booties on the floor

Why did I only just invest in a pair of heeled booties? They are refined enough to make me feel like I’m not being lazy, not to mention their ability to lengthen the leg. The strangely nagging word bootie does no justice to the wonder of the shoe.

Here’s the best part: basically every time you wear them out, suddenly it feels like you’re Anne Hathaway trotting around SoHo for brunch or whatever in The Devil Wears Prada.

Booties have both wonderfully chic and sensible characteristics. While black is more popular, I opted for a beautiful deep brown to increase their urban look.

Mixing patterns and colors is OK

I used to be very particular about making sure my winter scarves and hats matched my outfit. But as with the ballet flats, I’ve come to realize that mixing patterns with winter accessories can be an extremely endearing look.

Are you doubting your striped shirts; overalls; yellow, plaid wool scarf; and red beret? I’m sure your bleak winter landscape needs a little color. I’ve also found that on days I don’t want the wind to ruin a particular hairstyle, tying a silk scarf around your head à la ’50s housewife running errands keeps everything in place without crushing your hair.

Layering tights

If you have decently thick tights, layering two pairs makes much of a difference without hindering your mobility.
You can also go for layering a pair of colored tights under pants, which lends more warmth to your legs and adds an extra touch of personal styling if they become exposed.

Simplicity can make a difference

Cashmere makes all the difference. You’ll wear your cashmere crewneck sweater more than anything in your closet.
It does wonders for your hands if it lines your leather gloves. On the topic of linings, find an overcoat that has one.

I wear my London Fog trench under any condition because it has a removable lining and keeps me that much warmer (and obviously aids me in pretending I’m the subject of a French mystery film).