I always consider three things:
- What am I doing today and how long will I be on my feet. Today I will be working all day in the Cambridge store on my feet helping customers. From work, I am going out to dinner and drinks. So I will be in my footwear for at least twelve hours, maybe more. This calls for two pairs of shoes. I will start with flats then change to heels, and probably back again! Which reminds me, if you don't already do this, always keep a pair of small simple black flats in your bag, car, or at work to change into if your feet hurt. Because walking through town barefoot is never okay. Unless you are a marathon runner-even then Vibrums please.
- The second consideration is weather. Check the forecast for rain snow etc.
- Style. I am a big fan of the bright colored pumps and flats. I have a pair of bright blue pumps that I wear alot. They punch up everything from gray jeans to an orange dress. My yellow flats have the same effect. Combat boots are great too. I am so happy to see all the great combat boots out right now. They are thinner and more feminine than the army boots I used to wear back in the day, and they look great with everything from dresses to skinny jeans. They are comfortable too. They are a perfect option for a day when you will be on your feet all day. And on a date, because yes men like heels because they are hot. But the best dates are spent walking/partying through the city for hours not once thinking about your feet. What it comes down to is: sore feet can make you grouchy, and no matter how slamming that outfit is, you won't look cute when you're whining about your feet.