We recently spent ten days in Namibia. It was our first time out of the country since the world turned upside down in 2020, and whilst it was just across the border, it felt amazing to finally have a new stamp in our passports. And I’m excited to get started on some proper travel content after such a long time.

The first half of our little holiday was in Swakopmund. The weather was lovely – cool (sometimes cold), but no rain or wind – and the beach was across the road from our accommodation. We spent the remainder of our time in Windhoek where it was so hot and sunny, I pretty much forgot that we’re heading into my favourite season back home.

Let’s just say arriving at OR Tambo in a sundress and Ipanema sandals that night wasn’t my cleverest moment. It was, however, a good reminder that I’d been needing to shop for boots before Winter officially arrived. I’m covered for casual days – I have my trusty Timberlands, some cute leather booties, and a pair of chunky black boots. What I need this Winter is a new heeled boot that will look good with trousers or a dress. A pair that’s a bit more formal, or “dressy,” as my gran used to say. 

Unfortunately I couldn’t head straight to the mall on this important mission, because I decided to get sick with flu after our trip. Fortunately though, I am an expert level online shopper. I found some great options, and I’m sharing them with you in case you too are on the hunt for the perfect Winter 2025 boots. You can find them all here, if something catches your eye. 

Knee High Boots

This is ALLY. How beautiful is she? Simple, elegant, and a gorgeous block heel. She’s from Steve Madden and retails for R2399. The only thing that makes me nervous is seeing so many women on TikTok say that Steve Madden heels are terribly uncomfortable. I don’t know if that applies to the boots as well, so I’d love to hear from you if you know. I don’t want to pay that price for a boot I can’t really wear. 

I looked for a similar style, and found this one which is friendlier on the budget (and possibly on the feet as well, because of the lower heel). Does it call my name as loudly as the first one? No, but it’s still a cute option. Jet’s Rider Boot retails at R450 and I also saw it in a chocolate brown suede. 

I’m not usually a white boot girly, but this right here is a stunner. I tried to scroll away, and failed. Slouchy boots are everywhere at the moment, and I feel like this is one of the cutest ones I’ve seen. Oh, and did I mention it’s on sale at The Fix for R450? That’s a solid reason to add it to your Winter 2025 boots collection.

This is Foschini’s slouchy boot. I like the heel and structure of the previous one more, but I think this one needs to be tried on. I feel like the pic may not be doing it justice. It retails for R899 and there’s also a black option. There’s no girly name, just look for “Knee High Slouchy Boots.”

Ankle Boot

Why are my favourites always the most expensive? (Just a Girl plays in the background) The leather Ringer boot from G-Star may not be formal in the traditional sense of the word, but she is a beauty. Love the heel and that contrast coloured sole! Retails for R3899. 

Another pretty heel, this is the Tan Kylee boot from Butterfly Feet. I feel like this is a great colour for Winter, and I especially like how it gets darker at the toe. Kylee will set you back R899. 

Ankle boots proving that they can do slouchy too. This cute little number is on sale right now for R310 at The Fix! She just goes by “Brown Square Toe Heel Boot.”

I love the look of these Jacqui Block Heel boots from Cotton On, but I fear they may not be the most comfortable. When adding them to the post, I realised that I liked them so much because they’re kind of the boot version of my beloved Cotton On heels which are equal parts gorgeous and uncomfortable (see pic below for reference. If you squint a bit, you’ll get what I mean about them being similar).

The boots could be super comfy though, and all of this may just be me rambling. Jacqui retails for R699. 

Fold Over Boots

I know this style isn’t for everyone, and this is the first one that I’ve actually really liked. I think it would be super cute with a flowy little dress and stockings. It’s the Whipstitch Western boot from Foschini and retails for R1299. 

I’ve included this one for the girls looking for something a little edgier. This is Sissy Boy’s Black Spat with Buckle boot and retails for R1299. 

I thought this was actually a great boot to round off the fold over finds. It’s the Brown Western Heel from The Fix, and it’s on sale for R450 which is perfect if this is a trend you really want to try without spending too much. 

Hope this little list helps with the search for your Winter 2025 boots. ❤️

Disclaimer: This post is written in collaboration with Bash. All thoughts shared in this post are my own.