Don’t Let Your Outfit Flop: How to Wear Flip Flops Fashionably

OK, I know, I know, I know… Flip flops, UGH gross.

Flip flops have a stigma.

How to style flip flops fashionably

They just aren’t a pulled together outfit kinda shoe.

While they don’t seem fashionable, flip flops are practical for rainy summer weather and lazy days… and they totally can be fashionable if you stop overthinking it.

Mary-Kate and Ashley Olsen have become my unsung hero for cool flip flop outfits — did you even realise that they wear flip flops relatively regularly (and in NYC to boot)?

Did you realise that Carolyn Bessette-Kennedy wore flip flops too?… Even when she wasn’t in the Vineyard.

Did Kate Moss’ vacation flip flop outfits slip past your Pinterst perusing? Maybe you also overlooked some of her 90’s flip flops outfits?

Kate Moss, Mary-Kate Olsen, and CBK in stylish flip flop outfits

Perhaps I’m justifying my flip flop wearing, but these women clearly understand/stood that flip flops can look good.

Their penchant for flip flops flew under the radar because of how they style them.

Flip flops, when styled properly, can just disappear. When styled correctly, they can even add a nonchalant vibe to an outfit.

1- Keep your outfit monochrome or painstakingly simple so that the flip flops just blend in.

2- Keep the focus on the upper half of your outfit (e.g. earrings, necklaces, cool bag, etc…).

3- Long pants or flared pants look really cool… but skinny jeans with flip flops work really well together too.

4- Slim leather flip flops will pull your outfit together more than thick rubber ones.

5- Get a pedicure/paint your toes — this could just be me, but painted toes make feet look a lot better.

Note: The flip flops featured in these outfits are Havaianas or TKEES, you can find my full review on TKEES here.

How to Wear Flip Flops During the Day

How to wear flip flops casually
Left to Right: Sleeper dress with Celine sunglasses and an Isabel Marant clutch; Vintage Levi’s denim skirt (from WGACA) with a James Perse t-shirt, Celine sunglasses, and a Prada Nylon bag; Rag & Bone denim shorts with an Isabel Marant Étoile shirt, Celine sunglasses, Isabel Marant x HM earrings, and a Celine Small Trio; Rag & Bone skinny jeans with Rag & Bone sunglasses, Re/Done tank top, and a Prada Nylon bag.

For these flip flop day outfits, the long dress and denim skirt play up the colourful Havaianas.

… while the black TKEES blend into the all black denim look.

There’s a lot going on in the denim shorts outfit and colourful Havaianas would overwhelm it, so black TKEES (surprisingly) add a lot to it by not adding a lot.

How to Wear Flip Flops at Night

Flip flops outfits
Left to Right: G. Label dress with Jennifer Fisher x Goop hoops, and a Chanel bag; Erin Wasson x RVCA trousers with a J. Crew tank top, and a Balenciaga bag; La Perla slip dress with Jennifer Fisher x Goop hoops, Kate Moss x Topshop Belt, and a Chanel bag; Rag & Bone skinny jeans with a T by Alexander Wang cami, vintage earrings, and a Kate Moss x Topshop bag.

Yes, you can wear flip flops during the evening.

Just think: “What Would Kate Moss Do?”

This means adding jazzy vintage accessories wherever you can, trying to keep the look as monochrome as possible, and playing with proportions (i.e., flowing bottoms = tight top).


1- It’s safest to go with black or skin tone flip flops.

2- Decide if you want to go leather for more of a put together look (note: this isn’t rain proof) or…

3- Do you want a more casual look with thicker rubber flip flops (note: rain friendly)?

Cool flip flop outfits

Whatever you do, don’t overthink your flip flop looks.

Overthinking an outfit in general isn’t good and overthinking a flip flop outfit just adds insult to injury.

Let’s be real, flip flops insinuate that you don’t care. And not caring is cool, right?

If I’ve learned anything, caring is cool… but for the sake of flip flop outfits, just don’t care.

So don’t care, throw ‘em on, and say “I don’t care because at least I’m not ruining my expensive sandals in the rain!”

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