Skip to content
Vanity Fair Fashion
Fashion

Hesitate No More—These Are the Absolute 6 Best Shoes to Wear With Bermuda Shorts

By Swedan Margen

Hesitate No More—These Are the Absolute 6 Best Shoes to Wear With Bermuda Shorts

After years of short shorts dominating the summer agenda, a more tailored alternative has quietly returned to the spotlight and I, for one, couldn’t be more on board. Bermuda shorts have been bubbling up in the trend cycle for a few seasons now, but summer 2025 is officially their moment. Longer in length (typically grazing just above the knee), often slightly structured and always a little chic, they offer a polished yet effortless option for warmer days.

Still, despite their appeal, I’ve found that styling Bermuda shorts can bring about one particular conundrum: which shoes actually look good with them? Their in-between hemline and wider shape can throw off proportions if you’re not careful, but the right summer shoe trend can do wonders for balance, polish and overall impact.

After spending more time than I’d care to admit playing around with different pairings (purely for research, of course), I’ve found there are a handful of shoe styles that consistently work well with Bermudas—whether you’re dressing them up, keeping them casual or somewhere in between.

Below, I’ve broken down six of the best shoes to wear with Bermuda shorts this summer, all of which add something a little different to the overall look.

The 6 Best Shoes to Wear With Bermuda Shorts

1. Ballet Flats

@nnennaechem wears white denim Bermuda shorts with a pair of black leather ballet flats

Style Notes: Ballet flats add just the right dose of softness to the slightly androgynous mood of Bermudas. They help strike that balance between casual and considered and work particularly well with minimalist or classic outfits.

Shop the Look:

Bermuda Shorts

These will look instantly elevated, whatever you wear them with.

Prudence Ballet Flat

Reformation

Prudence Ballet Flat

These come in a handful of colours, but the soft tan is ideal for summer.

Ballet Pumps

A price that's hard to beat.

Leather Delfina Ballet Flats

Aeyde

Leather Delfina Ballet Flats

The burgundy colourway looks so high-end.

2. Heeled Flip Flops

@dawn.tan wears a black tailored Bermuda shorts with heeled flip flops

Style Notes: Yes, heeled flip flops are still going strong. Providing just enough lift to balance out longer shorts without making the outfit feel overdressed, it’s the styling trick I turn to when I want something that feels cool and elevated but not try-hard. Plus, they help Bermudas tap into their shared '90s fashion roots.

Shop the Look:

Linen-Blend Shorts – Black – Women – Arket Gb

Chic and breezy, this linen pair is ideal for wearing in the city and for the beach.

Kitten-Heeled Sandals

H&M

Kitten-Heeled Sandals

Mock croc finishes always look so luxe.

Freja Leather Thong Sandals

Staud

Freja Leather Thong Sandals

Contrast a white sandal with a deep burgundy or black pedicure.

Satin Kitten-Heel Sandals

ZARA

Satin Kitten-Heel Sandals

Brown and satin is a sandal combination I didn't know I needed.

3. Colourful Trainers

@holliemercedes wears cream Bermuda shorts with yellow trainers

Style Notes: For a trend-led take, try weaving in a pair of brightly coloured trainers into your Bermuda short ensemble. Ideal off-duty days or even travel looks, not only do they bring comfort, but they also inject a bit of personality and mirror the playful side of Bermudas. I like to keep the rest of the look pared-back to let the shoes pop.

More Fashion