Gather all of your shoes and boots in one spot.Divide footwear into seasons (summer, winter).Wear something comfortable you won’t trip over while trying on shoes.

Now you’re ready to start. Here are four things to ask yourself when deciding whether to keep or toss your shoes, boots, and athletic footwear.

Should They Be Fixed?

Busted shoes can often be brought back to life by a shoemaker, so don’t despair if a favorite pair is a mess. It’s typical to find wobbly and worn-down heels or broken zippers and buckles. But be realistic. Although quick fixes like replacing a heel are inexpensive and can give a shoe years more life, other repairs are more costly. It may be worth fixing a quality leather pair that should last a lifetime, but not so much for a trendy pair meant to last one season.  

Do They Fit?

Feet can grow and change shape even in adulthood. Don’t just assume the boots you’ve been wearing for 20 years will still fit fine. Try them on and take the time to walk in them. If you feel discomfort, you’ll remember why you never wear those pretty pumps! Here’s how to know if a shoe fits properly:

The toe box should be room enough or your toes will curl or chafe, resulting in calluses.There should be about 3/8 inch or 1/2 inch of space between your longest toe and the end of the shoe.The heel of the shoe should not slide around and your ankle should not come out of the shoe as you walk.The ball of your foot (the widest part of your foot) should not feel pinched.Look for arch support in the shoe or remove the flimsy factory insert and replace it with a better-quality off-the-shelf orthotic.

Are They in Style?

Shoes can date an outfit unless you own a classic pair of shoes. Shoe trends come and go; pointy toes tend to reappear every so often, for example. But some pairs of vintage shoes look in fashion even today. So how do you know what to keep or what to put in your time fashion time capsule?

Keep shoes and boots with block heels; they seem to stay in style, plus they are comfortable to walk around in.Keep away from oddly shaped heels (platforms and wedges).Keep simple, classic, and uncomplicated shoe and boot styles; footwear with too many cords, bells, and whistles usually don’t withstand the test of time.Keep an eye on what vintage styles may be considered classic; 1940s spectator pumps rule, and side-button shoes and bow pumps can look in fashion with the right outfit.

Do They Fit Into Your Lifestyle?

You may have a few presentable, well-fitting pairs of shoes that you can’t wear anywhere. Maybe you’ve left the corporate scene and now have a closet full of career pumps. Or you no longer feel comfortable walking in your perfectly preserved platform heels. Much like deciding when to toss clothes, evaluate if the shoes you’re left with match the image you want to project.