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One Woman’s Search For The Perfect Winter Boot

Not in Europe right now? Lean into the wintry weather with a perfect, practical ankle boot.

By Rebecca Tay

While I vacillate between fighting the urge to mute my friends in Europe on Instagram and obsessively watching (and re-watching) their Instagram Stories, I’ve been hibernating indoors, questioning the life decisions that mean I’m freezing my butt off while they’re over there… and wondering whether new winter boots might make me feel better.

The answer? They definitely help.

For versatility, nothing beats ankle boots, and this winter there’s a wide range of styles to choose from.

I’m personally most drawn to those with chunky soles, like these ones by Prada, Bottega Veneta and Camilla and Marc – perhaps because they’re so heavy that I just can’t go past their middle-finger attitude – but these more streamlined pairs by Aemery and Senso are also appealing and probably a little more wearable come spring.


Dress, St. Agni, $245, boots Alias Mae, $249.95

And when it comes to styling, I hate to break it to you, but the idea of chunky boots with something unexpected like a pretty floral tea dress or a lace blouse with a Peter Pan collar is usually more appealing than the actual look.

Yes, thick boots do look great with a flowing midi skirt or dress (like this one by St Agni), but the piece definitely needs to be loose or flowy enough to avoid being overwhelmed by a pair of big boots. And if you are going to go with a thick, lug sole, consider balancing out your bottom half with a chunky knit sweater on top.


Sweater vest, COS, $175, (similar here), navy skirt, Iris & Ink, $330, boots Ganni, $319

If you’re ready to graduate from skirts and dresses but, like your pant hems themselves, get stuck on what kind of pants go with chunky boots, you’re not alone. Do you tuck your pants in? Or should they be loose enough to fall on top? Right now, it’s definitely cooler to tuck your pants in. Opt for a pair of straight-leg jeans or cotton trousers, then tuck them into a pair of lug soles. The extra fabric (no skinny, peg leg jeans here, please) should be a tiny bit slouchy, in an ‘I did this on purpose’ way that then works well when finished with a utilitarian-inspired blouse such as this one.

So, while a new pair of boots probably won’t replace the feeling of Mediterranean sun on your face or a dip in the Aegean Sea, they might help take the sting out of winter.

A. Emery




Tony Bianco


Alias Mae




Tony Bianco


BY Rebecca Tay

Rebecca is a fashion writer who has worked for NET-A-PORTER and Victoria Beckham. You can find her stomping around Bondi most days in a pair of chunky-soled boots.

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