How to Not Look Like Your Mom (No Offense) in Bermuda Shorts

How Jess is styling her favorite summer trend.
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Staud Blouse (similar here), East Order Shorts, Staud Bag (similar here), Mari Giudicelli Mules (similar here)

Staud Blouse (similar here), East Order Shorts, Staud Bag (similar here), Mari Giudicelli Mules (similar here)

I get it. When you hear "Bermuda shorts," you think of awkward family vacation photos or tourists with no sense of style whatsoever. But hear me out: Personally, I'm grateful that Bermuda shorts are back. I acknowledge that they're polarizing and definitely not for everyone, but I find them to be one of the least risky fashion trends of 2019. 

Want to know a trend I was not a fan of? Daisy Dukes. I stay away from anything that reveals too much leg, and the Bermuda keeps me covered while also providing a bit of a challenge. How can I make a piece that's so outdated feel new and fresh? Newer designs include a high waist, which are significantly more flattering, and come in colors and patterns that actually feel chic.

I realize I'm fighting an uphill battle, so allow me to provide some visuals with a few ways to style my current favorite shorts, to ease you into the trend. I bet I can convince you to experiment with them—or at the very least, acknowledge that you could rock a Bermuda short. Here are a few of my favorite looks:

sat brunch
Staud Blouse (similar here), East Order Shorts, Staud Bag (similar here), Mari Giudicelli Mules (similar here)

Staud Blouse (similar here), East Order Shorts, Staud Bag (similar here), Mari Giudicelli Mules (similar here)

Offset the masculine shorts with a ruffled white blouse, a boxy handbag, and nude mules. You want to add a bit of sweetness without overdoing it, so keep jewelry to a minimum.


If you're walking around all day, the temperature is bound to fluctuate. Pairing the shorts with a sweater tank allows for some light layering, and sneakers let you log tons of miles without getting blisters. Practical, yet still chic.

Equipment Button-Down (similar here), East Order Shorts, Rag & Bone Belt (similar here), Gucci Loafers

Equipment Button-Down (similar here), East Order ShortsRag & Bone Belt (similar here), Gucci Loafers

This is by no means formal, but adding a button-down, thin belt, and loafers elevates the shorts to be appropriate for a meeting with a client. If this still looks too relaxed, add a simple blazer.


You want to be comfortable but still look put-together, so add a worn-in graphic tee and High Top Converse. If that's not feeling girly enough, add some dainty jewelry and a less structured bag for a feminine touch.

kelly text slide
& Other Stories Blouse, East Order Shorts, Mari Giudicelli Mules (similar here), Vintage Beaded Bag (similar here)

& Other Stories BlouseEast Order ShortsMari Giudicelli Mules (similar here), Vintage Beaded Bag (similar here)

This cropped take on a bowling shirt is one of my more versatile pieces, and it creates a straighter silhouette that gives me the masculine vibe I was going for. Give it some texture with a beaded bag and some suede black mules.

cas fri
AGOLDE Baby Tee,undefinedEast Order Shorts, Loeffler Randall heels, Vintage Blazer (similar here).

AGOLDE Baby Tee,undefinedEast Order ShortsLoeffler Randall heels, Vintage Blazer (similar here).

Usually Casual Friday translates to jeans, but Bermudas would work as long as you kept certain elements more professional. Add a plain white tee, a reasonable heel, and black blazer to pull it all together. 

If the Milah's aren't up your alley, here are a few other takes on Bermuda shorts that are calling my name...

  1. Black and Blue Striped Lia Short by Lovers + Friends, $39 (available in lilac here, $67)
  2. Denim Avery Bermuda Shorts by Free People, $78
  3. White Denim Hi Honey Bermuda Cut Off Shorts by Joe's Jeans, $138
  4. Black Bermuda Short by LPA, $79

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