Boots For Winter: How To Pick a Pair of Total Winners

Boots For Winter: How To Pick a Pair of Total Winners
Carly Jacobs

‘I don’t know, they’re kind of expensive.’

It was 2002 and I was heading on my first solo overseas trip. The boots I was trying on were $295, which back then was a lot of money. Especially as I was working part-time in a bar earning $18 an hour. That was 16 hours of work, a whole week in part-time land. Plus I was about to go the UK – I needed to save every cent for beer and West End theatre tickets.

‘Oh for god’s sake Carly just buy them! They’re perfect. They fit, they’re comfortable, they’re waterproof. You’ll get SO MUCH WEAR OUT OF THEM. It’s okay to spend money you tight ass!’ 

The lady helping us buy the shoes laughed. ‘Listen to your mother!’ She said. ‘They’re perfect.’

I hesitated for a moment and then bought them and wore them out of the store.

They were, without a doubt the best boots I’ve ever bought. Not only did they last me a full eleven years (I think they had their last winter in 2013), they were waterproof, unbelievably comfortable and worth every god damn cent I spent on them. Here’s me wearing them in 20092011, 20122013.

At the end of 2013 I took them to my boot maker and she sadly shook her head. The zipper was broken beyond repair and they’d been re-soled so many times there was nothing left to add a new sole to.

I was devastated. I went home and googled the brand and found out they were from a brand called Journey.  I desperately emailed the company asking if they might have a box of decade-old stock in a warehouse that had a miracle pair of my boots in it. No such luck.

Ever since then I’ve been super strict about my winter boots buying criteria. I’ve made a few mistakes since then but for the most part, I’ve nailed every boot purchase I’ve made. Yay me.

boots for winter


Dress from Frankie and Dash

Tights from Muji

Boots from Ecco


Here’s how I choose awesome winter boots…

1. Spend some $$$

About three years ago I impulse bought a pair of boots for $150. They were leather and seemed quite sturdy but they only lasted me two seasons. I thought that was okay for $150 but what really upset me was the effort I went to break the damn things in. Have you ever broken in a pair of leather boots? It’s weeks of wearing them around the house with thick socks and always carrying a box of band-aids with you in case you get sneaky blisters. This is why I only want to buy new boots every five years or so because I can’t handle the regular trauma of having to break in new boots. I’ve found that spending over $250 (at least) seems to be the magic number when buying boots. This is only based on my own experience but the two pairs of boots I’ve bought that have been over that threshold have been amazing purchases and all the boots I’ve bought under that threshold have sucked pretty hard.

2. Make sure they’re waterproof 

Fashion boots are kind of shit. Don’t kid yourself that a pair of boots from a fashion retailer are going to keep your feet dry and warm on a rainy day. They won’t. I bought a pair of fairly decent leather boots from a store that sells both clothing and footwear and after a month they started leaking. What a waste of money. For hard-wearing winter boots, I stick to boot and shoe specialists like Merrell, Ecco and Dr Marten. When I say ‘fashion’ boots I mean boots that are designed to look good, not necessarily be practical. Fashion boots have their time and place like if you’re going out for dinner but they’re not going to be much help when you’re schlepping through the snow on a walking tour of London.

3. Get ones with adjustable sides 

I’m a weight fluctuator and this extends all the way to my calves. If I gain a few kilos, I won’t be able to zip up leather boots unless they have elastic or buckles on the sides. Also sometimes I’m just retaining a bit of fluid and my legs are puffy. Elastic or adjustable sides are essential, especially if you’re planning on getting ten years of wear out of them. Most people tend to go up and down in weight over the course of a decade and elastic or adjustable sides will keep you wearing your fave boots no matter how puffy your calves are.

4. Make sure they’re able to be re-soled 

The more the sole looks like a traditional shoe with a separate heel and toe segments, the easier they will be to have re-soled. You can also ask before you buy them. When I bought my Ecco boots I asked if they could be re-soled and the staff said they could arrange re-soleing themselves. Awesome. I didn’t end up using that service because I have a bootmaker walking distance from my house but it’s nice to have it as an option.

5. Don’t go too small 

They need to be slightly firm to allow for stretching but just remember you’re going to wear socks under them. If you like thin socks, don’t stress too much but if you like wearing thick, warm socks, better go up half a size to accommodate. Also, take the time to get fitted properly in store. I’m a massive fan of buying things online but if I’m going to drop $300 on a pair of boots I’m happy to pay for the expertise of a trained person to help me get the right fit. As a rule, I generally don’t by shoes online because I have weird shaped feet from dancing as a kid. They’re kind of boney in weird places so I get blisters really easily. For most other stuff, I’m all over the online shopping but for shoes? I’m a bricks and mortar gal.

This outfit was worn for a day of meetings, client work and a whole bunch of other stuff. It’s turning out to be a rather busy winter…

Extra reading for the keen beans…

3 Australian Clothing Brands I’m Loving Sick Right Now 

I Bought The Same Dress In 3 Different Colours Because I’m a God Damn Genius 

What To Wear When It’s Really Freaking Cold Outside 

Tights: Where To Buy Good Ones In 2018

Winter Coats: How To Buy One That Will Last Ages

Have you bought boots for winter yet this year? Where did you get them from?

P.S Also you should totally sign up for my newsletter. It’s full of cool stuff.
P.P.S Don’t forget Crochet Coach has a free trial offer period at the moment so make sure you sign up!


  1. Cheney 3 years ago

    I’m breaking in two pairs of new boots (so I can wear them on alternating winter days for the next decade), so I’m all band-aids and thick socks right now. One are Dr. Martens in dark mulberry – a more grown-up version of the pale purple patent leather ones I bought when I was 13 with my first ever job money. The second are Redwing Iron Rangers in black. My partner’s a big fan of well-made shoes, and looks for boots with a welted sole so they’re waterproof and can be easily re-soled. Any time one of the brands he likes make women’s shoes (most don’t because it’s assumed we only want flimsy synthetic, yet still strangely expensive, shoes), I’ll check out if there’s anything I like. They’re never cheap, but cost per wear gets pretty amazing after a while.

    • Author
      Carly Jacobs 3 years ago

      Oh they sound great! I’ll look them up! I need a pair in grey or tan!

    • Hailz 3 years ago

      Hi Cheney. Did you buy your Redwings online or is there a stockist where you live? I love their boots!

  2. Erika 3 years ago

    Not this year, but last year, and the year before that. That would be 4 pairs, and all of them around $300 each. Two of those were from Redpath’s in Canberra 🙂

    Main criteria: comfortable, leather, thick (repairable) soles, fit my orthotics, wide feet and high arches (and also meeting my aesthetic requirements). Panama Jack flat black ankle boots (style is Felina). Old Florence flat brown zip ups (with elastic insert). Demeter flat black zip ups (bought up a size so the shaft is a bit loose – these were from Duo boots in England, so totally online ( but they were brilliant in responding to my not inconsiderable email enquiry). Matilda moderate heeled black pull ons – made to order so they are quite loose in the shaft, which I really like (

    Awesomely, NONE of these required breaking in. And I don’t expect to have to go boot shopping for at least 10 years….

    • Author
      Carly Jacobs 3 years ago

      That’s where I got my original boots! Redpaths are awesome. Also my aunty owns Boots for Broads! 🙂

  3. Hailz 3 years ago

    I seem to remember you having Frye boots? Would you recommend them? Their Melissa Chelseas boots are SO gorgeous, but for $550.. I’m thinking very hard. Also hard without trying them on.

    • Author
      Carly Jacobs 3 years ago

      Yes, I had a pair of black Frye boots and they’re awesome but my colour palette has changed a lot and I don’t wear black very often and I don’t love the look of black shoes if there’s no black anywhere else on my outfit. They take a while to break in but it’s worth it. I also found mine quite heavy after a full day of walking…

      • Hailz 3 years ago

        I was SO anti brown in the past, but I am after a brown pair of boots, so versatile and I think the same as you, not as ‘heavy’ as black. These are ankle boots so hopefully won’t be too heavy… I’ll keep thinking! Thank you 🙂

        • Author
          Carly Jacobs 3 years ago

          I look at brown as a neutral. Black weighs EVERYTHING down.

  4. Vanessa 3 years ago

    I cannot recommend Dr Martens boots enough. I bought a pair when I was fourteen, for $190 which was an astronomical amount of money to me then. They were my school shoes, then my work shoes, then my regular casual shoes. I’m 32 and those Dr Martens are still in my wardrobe, getting worn on at least a weekly basis. They’ve been repaired a few times and I’m meticulous about keeping them polished and conditioned but they are without a doubt the most hardy and wonderful boots ever.

    • Author
      Carly Jacobs 3 years ago

      I’ve never had DM boots but I’ve had DM shoes and they last DECADES!

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