Early Summer’s Unofficial Uniform: Jean Shorts & Tall Boots

A strong sense of personal style and formulaic outfit combinations might feel at odds with each other, but the reality is, having a repertoire of note-perfect pairings you can build an outfit from is essential. Take denim shorts and tall boots as an example. This look has surged in popularity in recent months — and for good reason. Simple enough in concept but impactful in practice, jean shorts and boots is the early summer outfit go-to. “I think it can be super flattering, great for the ‘in between’ weather, and on top of that, I’m seeing a lot of love for subtle western touches and this look kind of embodies all of that,” FRAME Chief Merchandising Officer Christina Holody tells TZR.

Why now? Its popularity might have something to do with the unexpected quality of the pairing. “A dressing technique that helps make an outfit interesting is The Contradistinction Technique, which is when you add an unlikely item to make an outfit more interesting,” Personal Stylist Elizabeth Cardinal Tamkin says, pointing to examples like pairing a menswear vest with a feminine skirt, a feminine dress with derbies, or — et voilà — boots with denim shorts.

But not all denim shorts play nicely with all boots. Understanding how to master proportions is key when testing out this look. “You can do a longer, more boyish short with a chicer and sharper heeled boot or a shorter, a-line short with a chunkier, higher-shafted boot,” Holody says. “What makes this look cool is how unexpected the styling can be.” For Tamkin, a baggier pair of shorts looks best with boots. “The shorts ideally have a flare to make the silhouette of the outfit interesting.”

Diving even deeper, Tamkin offers a theory called the Silhouette System™ that might shed light on how to pull this look off successfully. “We all have a ‘comfort' silhouette: The Palm, The Evergreen, or The Cypress,” she explains. “In short, The Palm likes to wear short bottoms with more bulk up top, The Evergreen prefers the inverse and likes volume at the bottom, and The Cypress likes pretty even from top to bottom.” The most commonly preferred of the three? The Cypress. “Adding boots with shorts allows Cypress dressers to wear them comfortably and with impact by taking the focus off the shorts and making them more even throughout.”

While summer’s steamiest temperatures might render tall boots an impractical choice, for the time being, this outfit pairing is well-suited for the season. Continue ahead for five ways to style the duo right now.

With A Vibrant Top

Balance out a pair of tomboyish Bermuda shorts with a colorful summer top and western-inspired boots. The combination is well-suited for the weekend and statement-making without feeling over the top. Finish off the look with a woven bag and bold sunglasses.

Sleek & Simple

If you’re easing into the shorts and boots pairing, consider a sleek and simple look that leans on a neutrals-only palette. This look feels like a nod to downtown style with its black top and accessories contrasted by light-wash denim.

Tonal & Textural

Embrace a bold tall boot by styling it with a tonal look, as seen above. If you’re a lover of white-on-white layering for summer, this would translate to an ecru palette seamlessly (just add sunglasses).

Coquette Inspired

Toughen up coquette-inspired pieces like rosette embellishments and bows with a pair of denim Bermuda shorts and tall leather boots. Despite the merging of two very different aesthetics, the contrast results in a well-balanced look.

Moto Moment

Looking for a way to wear your beloved moto boots post-winter? Try them with a pair of black denim shorts and coordinated top. The look feels classic and cool, with the right amount of edge. Finish it off with your favorite day bag.