I Tried 6 Fashion-Blogger Ankle Boots Looks For Those Iffy Autumn Days

Best part? You only need one pair of boots!


Wanita Nicol |

It’s not hot; it’s not cold. It was kinda warm; now it’s a little chilly. Yup, Autumn is a tricky one when you’re choosing what to wear. After all, the average weather app is about as reliable as Eskom. Well, you can’t go wrong with a pair of ankle boots. If it turns out to be hot, you won’t be stifled by a boot that rides up to calf height or above. If it’s cold, toasty toes go a long way towards keeping you warm. But, how easy is it to pull off those fashion blogger looks IRL? I found six popular ones and put them to the test.

Effortless Boots-And-Skinny-Jeans Combo

This was a natural fit for me because it’s essentially my winter uniform. The trick was mastering that fashiony-effortless look that says, “I look put-together without even trying” as opposed to my usual effortless look, which says, “I made zero effort.” After much scrutinising of blogger posts, I cracked it: flash some skin around the ankle and accessorise… a handbag, a hat, a scarf, a chunky jersey or a shirt tied around your waist. Boom.

fashion blogger ankle boots

I was relieved that that rolling up my jeans didn’t make my legs looks short.

Verdict: At first I felt silly, like I was wearing too many clothes. Why have a jacket when you already have a shirt around your waist? But I wore this outfit to the movies and actually got used to it pretty quickly. I enjoyed feeling dressed up for a change without the discomfort of actually getting dressed up. I’d wear this again.

READ MORE: “These Boots Are So Versatile You Could Wear Them Every Day – And I Did…”

Mid-Length Skirt And Boots

I love the uncomplicated style of this look, but I’m not really a mid-length pencil skirt kinda girl (I walk with purpose). TBH, I wasn’t even sure if I owned one. I eventually found a passable skirt in the bowels of my cupboard (Marie Kondo would not approve) that an ex-boyfriend had given me years ago. I can still hear his mother’s voice: “This skirt is a classic. Look after it and you can wear it for 10 years.” I can now add: Stash it deep in your cupboard after the break-up and it’ll still be good to go after 20! This is quite an open-ended style – some bloggers wear long, slouchy tops; others opt for a crisp, white shirt and blazer. But the simple jersey option looked most doable for a non-fashionable pretender like me.

fashion blogger ankle boots

You can’t go wrong with all black, right?

Verdict: It’s so simple – ideal for someone who has no time for agonising over outfit choices. And the skirt is actually fine for striding around town. This will be a new go-to for me.

Boots With A Flouncy Dress

In my early twenties I had a fleeting flirtation with boho – the film Moulin Rouge may or may not have played a part. (I also drank absinthe with sugar melted through a slotted spoon.) So I had to try this one for old times’ sake. The trick here seems to be in the colour of the dress – prints and white are the general go-to for bloggers.

fashion blogger ankle boots

I’ve often worn this dress with strappy heels. Boots are far more comfortable.

Verdict: Having left my boho days behind, this was a hard look to cheat with what was readily available in my cupboard. If I had a few tunic-style dresses though, I reckon I could nail it easily because it doesn’t need much accessorising. Plus, I like the idea of keeping my summer dresses going even as the weather turns cold.

READ MORE: The Boots Every Woman Needs Because They Work With Everything

Weekend Boots And Denim Shorts

I live in denim shorts on weekends, so this was another natural look to try – although usually I pair my shorts with plakkies. Problem is, while I’m fairly petite, the girls who pull this look off best are really skinny, as in that straight up and down, ectopmorph kind of figure. So instead of a crop top like I saw on many of the bloggers, I opted for a tank under a plaid shirt.

fashion blogger ankle boots

Seconds after this was taken, the dog pulled me into the flower bed. Hooray for sturdy boots!

Verdict: To my surprise, I loved how I looked in this outfit. So much so that I posted it on Instagram and other people loved it too. It’s the kind of look that will get you attention. Personally, I prefer not being the centre of attention though, so I doubt I’ll wear it again. But it was super cool to see that I can!

Opaque Tights With Ankle Boots

This one was pretty easy to get right. Opaque tights make anything look good, IMO. You can layer up with a scarf, coat or jacket that you can remove when Murphy’s Law strikes and the weather warms up.

fashion blogger ankle boots

Another outfit I would usually wear with heels. I love the idea of looking smart and still being able to walk!

Verdict: I wore this to work and I felt smart but not uncomfortable. If I had client meetings I could easily swap the denim jacket for a cropped blazer or cardigan. And the top can be long sleeve or sleeveless, depending on the temperature. The versatility makes it a winner for me.

READ MORE: “I Found The Perfect Heels: All Of The Height, None Of The Wobble”

Slouchy Boots-And-Leggings Look

The comfort of this appealed to me, but I worried about, y’know, that crotch area. The key appears to be a loose, yet slim-fit top just long enough to graze the tops of your thighs. And then all the accessories.

fashion blogger ankle boots

That smile when you can get away with wearing leggings as pants…

Verdict: This was the most comfy – hello, leggings! – but it has a lot of potential. I’d happily just wear the base layer (boots, top, leggings) out to the shops on a Saturday morning, but once I’d added a blazer and scarf, I felt dressed-up enough even for a dinner. I see myself wearing this one often as the weather cools.

How To Choose An Ankle Boot

Boots can be pricey, so if you can’t afford a cupboard full, invest in a few versatile pairs. Use these guidelines…

Quality over quantity. As with most things in life, a really good pair of boots that’s going to last is a better investment than a cheap pair that’ll fall apart before the end of winter.

Go with a neutral colour. It will give you more options. But match that neutral shade to the colours that dominate your wardrobe. I have a lot of black and white in my wardrobe, so these black CAT Showdown ankle boots were the perfect fit.

fashion blogger ankle boots

The CAT Showdown boot that I wore comes in black and dark brown.

Wide cuffs for slimmer ankles. A cuff that sits loosely around your ankles instead of hugging them will make your lower legs look slimmer.

Round toe for comfort. If you walk a lot, opt for a flat sole and a round toe, so your feet don’t get cramped. The sturdy sole of this boot cushions my feet and the cut out in the middle creates the illusion of a slight heel, so I can get away with wearing them to meetings.

The CAT Showdown boot is available in black and brown and goes for R2 100. Check it out here.

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