The hardest thing in Chicago is dealing with the manic-depressive weather that surrounds us. In the morning you leave your apartment in a skirt and skimpy tank top, and then the clouds gather, the wind picks up, and you find yourself running home between classes to grab some more layers. But aside from trying to guess the afternoon’s temperature, many readers have asked me how to wear the chunky heel that I idolized last week. Here are a few hints and tips on how, when, and where to wear the chunk.

I always find it best to wear a chunky heel, wedge, or espadrille shoe with a nice pair of capris that flair out ever so slightly. The effect is very slimming because your skinny ankle is shown next to not only a flair but a large heel as well. Wearing culottes or gaucho pants with a large heel can be a bit risky depending on your body size. I am a very curvaceous mamacita, and I tend to stick to capris since they are more flattering.

Skinny pants, which are all the rage right now (but which I have a feeling will disappear quite soon), can also be worn with a larger chunky heel. Once again, the effect is the same as with capris. Clearly this is another combination to be worn only by the brave.

A chunky heel can be mixed with a skirt, depending on the skirt’s length. I find that skirts that hit the leg at the calf do not flatter the body at all, and adding a chunky heel on top of that only makes matters worse. On the other hand, a very short skirt mixed with a chunky heel can look very…suggestive. I recommend matching chunky heels with a skirt that hits around the knee, preferably slightly above. Dresses can easily be matched with a chunky heel and should follow the same rules as a skirt.

But when and where should a lady be wearing such outfits? I find that I wear my most fun pieces out at night. When going downtown to a bar or a party, I will usually wear my cork wedges with lots of sequins on the front. They are often a conversation starter and can spice up any outfit. Depending on the temperature, I usually wear a tiered green skirt that hits my knee and a tight fitting top. During the day a combination of pants and chunky heel is more appropriate. This look is more toned down but also fun to wear and makes me feel confident. T-shirts can be worn with this outfit, making it comfortable and not too dressy.

Any way you wear it, a chunky heel can be quite a risk. Just remember to look at where your clothes are hitting your body. Is it flattering? Would it be better to hike the skirt up a notch or just throw on some jeans? While color can be playful, fit is the most important thing to me, and when it doesn’t fit, a whole outfit can be ruined. Maybe a smaller heel will help meld the outfit. There are many factors to take into account, but just remember clothes are how we display our bodies, and we should be proud every day.