It’s fun to follow trends and keep track of how they either evolve or fade away each season. I’ve kept a close watch on the “booties” or “shooties” trend which resurfaced along with the resurgence of 80’s fashion. The trend was a fringe statement three years ago but has grown into a mainstream look. Fabulous.

Booties and shooties started out being described as peds that looked both like a shoe and a boot. I’ve found that over the seasons, this definition has become a little loose. What I used to call an ankle boot is now also being described as a bootie. So to keep things simple in this post, I’m going to refer to all styles of ankle boots and booties as booties.

Wearing booties under boot cut and wide leg pants or jeans is a no-brainer. Even though you cover up most of their style detailing this way, it keeps the leg line long and that’s instantly flattering. Wearing booties with skinnies or straight leg bottoms showcases more of the ped and is a little more daring. Wearing booties with skirts and dresses is the most daring combination simply because high vamped shoes cut the leg line, especially when there is a strong contrast between the colour of the shoe and the colour worn on the leg.

Patent Mind BootieKinna Ankle BootieVanessa-leather-bootieRosegold

I love a fashion challenge. If you would like to experiment with the trendiest option, here are some guidelines for wearing this “of the moment” fashion ped with skirts and dresses:

  1. Adjust your eyes to the look: It’s always the first step! We have been brainwashed to believe that high vamped shoes do not work with skirts and dresses. True, this pairing often looks dumpy. But by adjusting the rest of the variables of an outfit, AND by getting the right style of bootie, you’ve bent body type guidelines and made the look work.
  2. Keep the leg line one colour: The easiest way to achieve a longer leg line is by keeping the hose and booties a similar colour. So black booties with black textured hose is a simple solution. Add a dress in a similar colour into the ensemble mix and you’ve created an even longer leg line.
  3. Keep it heeled: Even if it’s only an inch or two, the extra height helps to balance our proportions. Stacked three to four inch heels are best for this look, but never fear. Unless I’m sitting down, I don’t wear heels that high and you can make the look work with lower heels too. Short flat booties are not a no-no, but it’s a hard look to get right.
  4. Expose the knee cap: As with mid-calf boots, shortening the hemline just a tad is important. Remember that you can cover up with hosiery if you prefer more leg coverage.
  5. Choose a flop proof style: Booties that are cut low and fit close to the ankle tend to look more flattering (like the pair on the left above, and the round toe BC bootie). The Clarks “Cone Sweet” bootie is an excellent style to wear with dresses and skirts because it fits close to the ankle and actually has a low-ish vamp.

Once you’re confident sporting booties with skirts, you can move to YLF graduate school. This means dropping the second guideline and wearing the look with a high colour contrast between the foot and the leg. If you’re already sporting the advanced version, well done. It took me a while to graduate to that level, but I’m there now and enjoying every minute of it.

My guess is that the pairing of booties with skirts and dresses is here to stay, so don’t feel that you’re coming in on the end of a trend. It won’t be too late if you get cracking this season.

BC Footwear Swear Clarks Cone Sweet

Two of my favourite booties right now, both of which are in the YLF store.