I Won't Wear These 5 Shoes With Maxi Dresses—Here Are 5 I'd Choose Instead

Summertime is synonymous with dresses, and with each return to the warmest season, we reach for the easiest styles to get dressed in that require little thought and time, ensuring we get out of the house and into the sun as quickly as possible. And this year, it's all about maxi dresses. 

After the mini hemlines of last year, the maxi silhouette is a welcome respite; long, languid and perfect for breezy days, plus you you won't have to worry about having a Marilyn moment. The maxi is the laid-back dress we all long for, and when it comes to styling with shoes, there are a few tricks to really make the most of this piece. Though I'll never completely write off a style of shoes, there are certain pairs that work harder than others, look more considered and ensure you celebrate a long hemline in the best way. 

Now, let's get to it. Here are five shoes I'm wearing with maxi dresses, and five I'm avoiding right now. 

1. Wearing: Fisherman Sandals

Avoiding: Flip-Flops


(Image credit: @sasha.mei)

Style Notes: There's no denying that fisherman sandals are having a moment. Since their revival last summer, the style has only gained in popularity and continues to prove they really do go with anything. To instantly upgrade a simple maxi dress to a fashion-forward ensemble, simply add fisherman sandals. 

Shop the look:

2. Wearing: Retro Sneakers

Avoiding: High-Tops


(Image credit: @vivian.yrl)

Style Notes: If you love a trainer pairing, I'd advise you go for a retro silhouette. Not only is the shape more streamlined, allowing for the focus to remain on the dress in question, but they work especially well with dainty dresses by employing the "Wrong-Shoe Theory"

Shop the look:

3. Wearing: Strappy Sandals

Avoiding: Chunky Sandals


(Image credit: @shhtephs)

Style Notes: Don't get me wrong, I'm a big fan of chunky sandals. But their heavy form can easily drag an outfit down, especially when you're playing with ankle-skimming lengths. To lighten the look, opt for a refined strappy sandal. 

Shop the look:

4. Wearing: Minimalist Boots

Avoiding: Cowboy Boots


(Image credit: @oliviamarcus)

Style Notes: As a big fan of cowboy boots, it might come as a surprise that I'm skipping them for now. One of the identifiers of cowboy boots is in the curved silhouette of the sides, which are often embroidered, and these intricate details aren't appreciated when covered with a long skirt. So, keep it simple and let your favourite minimalist boots earn their keep instead. 

Shop the look:

5. Wearing: Ballet Flats

Avoiding: Loafers


(Image credit: @_marisamartins_)

Style Notes: As much as I love loafers, there's definitely a time and a place for them. And when I'm styling a maxi dress with flats, I tend to lean towards a more delicate ballet style, especially when it's a dressier pair. 

Shop the look:

Next Up: 8 Easy Summer Outfits I Can't Wait to Copy

Florrie Alexander
Acting Affiliates Editor

Florrie embarked on her fashion journey while studying French and History at university. Whilst studying in Aix-en-Provence, she began to write her dissertation on the history of fashion and the influence of Haute Couture, and landed her first role at Harper’s Bazaar. Following this, she interned for various publications including Elle, Grazia and Marie Claire before joining the fashion team at Conde Nast Traveller. There, she contributed to international photoshoots, styled pages and covers, and produced engaging digital content.

During a freelance period, Florrie honed her skills in editorial work in various digital and print publications including Vogue Italy and Departures magazine, as well as styling e-commerce photoshoots and personal shopping. Florrie actively pursues an in-depth understanding of fashion and jewellery, and after styling a jewellery cover shoot at Conde Nast Traveller chose to complete the De Beers Diamond Foundation course. Florrie first joined Who What Wear UK as a freelancer before becoming the Commerce Writer, blending both editorial and commercial content. Now, as the Acting Affiliates Editor, she monitors current trends, new-in styles, wardrobe heroes and how best to style them. In her downtime, Florrie can be found in her hometown of London, usually with a coffee in hand.