Before I went to St. Louis, I went on a bit of a shopping spree. The weather was heating up, and I knew I wanted to get a couple of summer dresses. As I tried a pile of dresses on, I put each one through a rigorous set of questions:

Can I teach in this? My professional dress code isn’t that strict, but dresses with crazy cleavage need not apply.

Can I bike in this? Too short and I’ll flash oncoming motorists; too long and it could end up caught in my spokes. If it’s not stretchy enough, it will limit my range of motion; if it’s too loose it will billow like a sail.

Do I look great in this? Sure it’s bike-worthy and work-appropriate, but if I feel frumpy headed out for a drink with friends, what’s the point?

Is this easy to wear? If it requires serious bra strap permutations, special underwear, or anything under/over it, it’s too complicated for me.

As you might imagine, only one dress passed. Sometimes I swear women’s fashion designers just assume you’re going to be walking 100 feet from your car to your office. Lame! You can get some more bike style tips from the awesome blog, Let’s Go Ride a Bike.

(Photo credit: Dottie at Let’s Go Ride a Bike.)

On the next episode of Clothes that Work: rigorous questions to ask your concert outfit.