For some people, I’ve heard, saddle shoes are synonymous with frumpy 1950s-era outfits or the type of shoes your mom would force you to wear to school-pictures day in grade school or whatever. But for me, they’ll always be the ~ultimate~ cool-girl shoes and not frumpy in the least. I mean, they were part of Audrey Horne’s signature look. You can’t get cooler than that, in my opinion. Here are some more reasons why I love ’em (and why I think you should, too):

• They can add a little retro flair to an outfit without making it look all costume-y.
• They’ll go with virtually everything in your closet. (I think this has something to do with their being two colors?)
• They look SO GOOD with bobby socks, especially the frilly kind.
• And you don’t even need to be an obsessive thrifter/vintage shopper (this would be me, oops) to get in on the two-tone fun, either! Making a pair of your own can be as simple as throwing some paint on a pair of canvas flats.

Materials you’ll need:

  • Plain round-toe oxford or Keds-style shoes
  • Some fabric paint—Tulip brand (Soft Matte variety) is the stuff I like to use. Any color will do! You can go with black for a classic look, or try bright yellow or robin’s-egg blue for more of a spring vibe.
  • Two paintbrushes: a large-ish one for covering the main area of the shoe and a small one for detail work and hard-to-reach areas.
  • Masking tape
  • If you’re gonna do wingtips you’ll also need an X-ACTO knife and a pen for marking.

Taping the shoes:

1. First, sketch out your saddle pattern. I was lucky enough to find a pair of shoes that already had a very similar pattern built into the shoe itself, so I just followed that. If your shoes lack an already existing guideline, you’ll need to sketch one out on the shoe with a pencil or tailor’s chalk. If you’re not quite sure of what type of pattern to use, a quick search around Google should provide you with some good examples.

2. Next, start taping off the shoe following the pattern. Typically, the toe and heel areas are left plain white, surrounded by a black “saddle” design. The main places you’ll want to tape off are the toe and the heel, the sides of the soles, and the edges along the shoe opening. You can cover the shoelace grommets, too, but it’s not really necessary. Usually, fabric paint can easily be cleaned off of plastic or metal with a wet Q-tip.

3. Here’s what the shoes look like all taped up. You can just leave ’em like this and start painting for a more “authentic” saddle look, or you can get all fancy-schmancy like I did and attempt a wingtip pattern! It’s totally up to you. I’ll show you how I did it in the next step…

Making the wingtips:

1. Using a pen, sketch out your wingtips. I used the middle opening of the shoe as a guide to make sure my design was centered. Extend the wingtip lines out and back into the side seam area near the top of the shoe. It’s basically like drawing the top part of a heart, extending it outwards, and then stopping halfway down the heart. Do this on both shoes.

2. Now, carefully run your X-ACTO over the pattern you just drew. Use only enough pressure to cut through the masking tape, not enough to cut through the shoe itself!

3. Peel the tape away to reveal your new pattern!

Painting the shoes:

After all that tedious taping, we can finally get on with the easy part: painting! Yay! All you gotta do is fill in all the non-taped areas of your shoe with fabric paint. Even though the tape is there to prevent any bleeding, it’s not always foolproof. So be sure to take extra care while painting near the tape-edged areas. Work slowly and use only small amounts of paint at a time (don’t glob it on). Do two coats of paint if your first doesn’t come out opaque enough.

After the paint dries, peel off all the tape to reveal your cool new two-tone shoes! ♦