How to Wear Bermuda Shorts (Without Looking Dowdy)

We have four words that will stir both confusion and possible excitement in those shopping for their 2020 spring wardrobe: Bermuda shorts are back! No, seriously. Remember in the ’80s and again in the early 2000s when everyone had a pair of madras Bermuda shorts? You know, those patchy-plaid knee-length shorts many of us wore with flip flops or boat shoes? Well, they are back — without the madras print or the boat shoes (thank goodness!).

Here’s the good news about this trend: It no longer carries a dowdy connotation, and it can actually be super stylish and chic. When worn correctly, this is a great look for almost any warm-weather occasion. Whether paired with a cotton blouse or a light sweater with some cute tennis shoes, this look is being redesigned for the 21st century. Even brands like Lucky and Reformation are getting on board with the Bermuda shorts comeback.

That being said, there are a few rules to live by to pull off this look. Here’s our take on the Bermuda shorts trend, along with some helpful tips and tricks to wear this comeback in style.

How to Wear Bermuda Shorts (Without Looking Dowdy)

Rule #1: Opposites Attract

If you opt for some looser-fitting Bermuda shorts, then accent the ensemble with a fitted top. Our favorite way to wear these shorts is to pair with a fitted J.Crew tee and some leather sandals. It gives you the right amount of shape and is great for just about any casual outing.

Michael Stars’ Spring 2020 line features some fabulous Bermuda shorts options. Here, the “Sybil” linen Bermuda shorts are paired with a simple, white, fitted tee. Image: Michael Stars

A flared Bermuda short with a fitted top creates a flattering silhouette. Pair them with a fun pair of leather gladiator sandals for a perfectly on-trend look. (SB TIP: All black elongates the body!) Image: Agolde

Rule #2: Avoid Low-/Mid-Rise

Bermuda shorts have the potential to be less than flattering on most figures. So, it’s wonderful that the high-waisted trend that’s becoming on so many is still very much in. When wearing this look, be sure to find a Bermuda short that is high-waisted to accent your figure.

Bonus points if you can tie the perfect bow with your belt. The key is to be okay with imperfection; you don’t want it to look too perfect! Image: Boden

A high-waisted pair of Bermuda shorts offers a flattering silhouette. Image: Neiman Marcus

Rule #3: All About Proportions

Since Bermuda shorts cut off right above the knee, they can make even the longest legs look short. An easy and elegant way to elongate the legs while donning this trend is to throw on a heel. Find something versatile and fun — a tall, strappy heel or a playful kitten heel would both work well.

These Sam Edelman strappies are a great selection to wear with just about anything, and they look perfect with Bermudas. Image: Revolve

These playful kitten heels take denim Bermuda shorts up a notch. Image: Frame

Rule #4: Be a Little Daring

When trying out a new trend, why not be a little daring? Invest in an effortless set — preferably one that brings some color — for those days when you just don’t feel like putting much thought into your outfit choice. Something bright, colorful and already put together will become your go-to summer selection.

We love this bright pop of color, not to mention the fact that it’s a set! Image: Eye To Eye

Rule #5: Long Live Linen

We all know how quickly Southern weather heats up in the spring and summer. Linen is a breathable fabric ideal for almost any warm day in the Sout. And it can be dressed up or down — just add a matching linen blazer over a classic white tee for a more refined look, or give it an edge with some chunky sandals.

Linen is the ideal fabric for summer in the South — including for Bermuda shorts. Pair it with a linen blazer for an elevated look. Image: Neiman Marcus

Rule #6: Comfort is Key

Want to throw on an outfit that is both cute and casual? A comfortable Bermuda coupled with a cotton tank can be super chic while still offering you comfort. It’s the perfect look for taking the kids to the park, or simply taking a “me day” and getting a pedicure.

A longer pair of shorts, like the Bermuda, gives the appearance of a more put-together look and can actually align with athleisure comfort (yes, please!). Image: Athleta

Bermuda is back, and we’re on board with this updated trend — boat shoes not needed!

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