Edit: Seven winter flat styles we love

A local market edit of the season's best slides, ballet flats, loafers and clogs.

We were each on our way to an event when it arrived on my screen — a text from Soph with a pic and a question: is this absolutely cooked?

Soph’s iconic feet

The “this” in this question was, of course, Sophie’s besocked toes striving to bust through the tubular straps of this pair of sexy summer sandals.

Now, one thing you need to know about Soph is that she has an almost pathological attachment to open-toed shoes. So much so that she’ll (evidently) do whatever it takes to keep wearing them even when she runs the risk of frostbite. She’s also an iconoclastic Gemini who looks at tradition like a jungle cat looks at its prey, so this behaviour is pretty much par for the course.

But when we both rolled up to the event, I looked down at her feet and couldn’t help but admit: socks and a toe strap? Not no! With a long, wide-leg tailored trouser, it was a quietly iconic mix of casual and formal. It bopped the wrong shoe theory right on the nail.

We’re both fans of Allison Bornstein’s wrong shoe theory — which essentially posits that you should choose the opposite shoe style to the one you might ‘classically’ pair with your outfit. It’s why you see so many stylish women wearing open-toe flat slides with suit trousers, or hiking sneakers with voluminous, ultra-feminine dresses. It’s an easy formula to introduce tension to an outfit: relaxed shoe + elevated clothes = casually cool.

But closed-toe flat shoes — the kinds we tend to gravitate towards for the day-to-day as the temperature drops — tend to signal a more ‘formal’ aesthetic, making them trickier to style when you rely on wardrobe staples like tailored trousers, blazers, long-line skirts etc. All of a sudden, putting a closed-toe flat shoe with these items reads as too…stuffy? Stitched up? Grown up?!

Thankfully, adopting the wrong (flat) shoe theory in winter doesn’t always require leaning on sneakers day-in-and-day-out. Or slipping on a sock under those summer sandals, for that matter.

It just requires a little something extra from said flat shoe:

• Texture! It doesn’t need to be a crazy detail like studs or animal print — even a crinkled or patent leather will do the job
  Or

• Detail! For example, a square toe on a ballet flat makes them feel more subversive and less like a rehash of an early 2000s style trope (for us geriatric millennials, it’s simply still too soon).
  Or

• Accessories! Wearing a sock — be they sheer mesh or cosy cashmere — can easily walk a flat shoe out of conservative territory

In this week’s newsletter, Soph has sourced options for our seven favourite flat shoe styles for winter. You’ll find shoppable options for:

1. Ballet flats (non-traditional, round-toe)

2. Slingbacks

3. Square toe flats

4. Slides

5. Loafers

6. Pointed toe flats

7. Clogs (chic ones, we promise)

For ideas on how to wear a flat winter shoe, take a peek at our Pinterest board below.

Up later in the week: the best all day everyday boots on the market. Now, onto the shoes. Happy stomping!

Ballet Flats

I don’t know if there was a day in 2005 that I (Annie here) didn’t wear a ballet flat. My poison of choice was a beaten-up bronze pair, which I’d wear with a pair of Tsubi (yes, before it became Ksubi) black skinny jeans, an Alannah Hill cami and a vintage knitted bolero. In the era of The Simple Life and Amy Winehouse, this was considered by some (ahem, by me) to be the height of cool. I haven’t managed to bring myself to slip my foot back into another ballet flat since.

Until, perhaps, now?

These are the ballet flats that make us want to revisit the trend. Yes, the mesh numbers are very derivative of a trend that’s been circulating for a couple of years now and might be a controversial winter shoe recommendation — but we’re eager to see them styled with a sock. Will you be the first (style) dog on the (mesh shoe) moon here? Pair with a wide leg to give them less attention and bring it all down a notch.

Sophie just purchased the snake pair — stand by for feedback, caller.

1. SENSO / Cassidy II — $199

2. SENSO / Cordelia — $199

3. BASSIKE / Eyelet Detail Ballerina Flat — $650

4. SENSO / Cameron — $229

5. SCANLAN THEODORE / Ballerina Flat — $400

Pinterest

Slingbacks

A slingback requires a certain level of comfort with being a little bit uncomfortable. Not for long days hoofing it around the city, but a sexier option to be sure.

1. TONY BIANCO / Akita — $199.95

2. DOF STUDIOS / Paulina — $349.95

Square Toe

The ballet flat’s cooler older sister. A square toe instantly transforms this classic silhouette into more interesting territory. We love interesting textures to push it one step further. Are Essen’s fuzzy black shearling pair the perfect winter flat?! Our frosty toes certainly want to say yes.

P.S. for a couple of lucky pairs of feet, there are still 2 sizes left in these, too.