Tucking your pants into boots has been around for quite some time (we all remember the classic: tucking skinny jeans into knee-high or thigh-high boots). However, this fall, the styling trick — a staple as we transition seasons — has a fresh and modern silhouette with a little nod to the 80’s.

When I initially saw the trend emerge, I was admittedly a little nervous… It seemed very editorial, or should I say “straight off the runway.”

The silhouette was a little more theatrical.

The pants were baggier, the waist higher.

Screaming major 80’s supermodel.

But, as the weeks went on, I saw some of the most style-savvy people I know wearing the trend, they adapted it in a more casual, wearable way and seeing it on regular people (not runway models) gave me a little more confidence to try it out . It encouraged me to experiment and find a formula that would work for me.

My Approach:

As a fashion philosophy, I try not to look too overdone and I generally shy away from looking too va va voom. Integrating sweet, femme details was important to me to get this look right for my personal aesthetic.

The Styling:

I tried many looks: from untucked blouses to oversized sweaters and multiple boot styles. I experienced many failed attempts, and — not going to lie — a few times I convinced myself I couldn’t leave the house, fearing I might resemble a Pirate or Puss In Boots. It felt too “out there” and just something so different to what I usually wear.

After much procrastination and many evenings researching street-style images and my favorite fashion designer’s I finally found a balance, a more pared-back, approachable way of wearing this trend. I noticed the people that do this best were using a structured boot, one that can keep its shape. I noticed as well that a lot of these muses were approaching the pairing in a monochrome color palette for an especially interesting take on the trend. Adding a bright bag or some fun accessories to break it up.

(I also noticed a trick: try tucking your pants into your socks or put a rubber band over the pants at the ankles to keep them from getting pulled in the wrong direction and to control the billowing.)

Now, I was ready to go for it (as the saying goes “you gotta own it.”) and wear it with confidence. Readers, I found the perfect styling secret!

The Result:

This season’s style trick is to create this silhouette in a fresh and modern way. First, choose pants that are slightly baggy in shape and tapered at the bottom to allow for an easy tuck into the boot. The boots should be a little roomy at the top to allow for the pant to puff over ever so slightly… (Too much and you veer into aforementioned pirate territory…) The boot can be calf height or knee height. On the top half, I usually go for an ornate buckle belt and a femme blouse tucked into the waistband. I usually love high-waisted pants to balance out the proportion but, honestly this outfit can also look chic (and transition seasons seamlessly) with a turtleneck or a cozy sweater. Just make sure the sweater isn’t too chunky and has a balanced proportion to the pants.

The Takeaway:

This trend has strong staying power… We can’t get enough of it, so give it a try! Need more inspiration? See three ways I took on the trend below: