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5 (splendid) Ways to Wear Riding Boots

Published 10/10/2014 by

Are your calves cold? Or do they have a fever? The fever being the sheer NEED to slap on riding boots. Don’t deny yourself. You should do it. These boots are not just an investment to ward off low cool breezes (so many breezes) but they’re an investment in your future, more chic self. PICTURE IT NOW. It’s all happening isn’t it? You are Blake Lively/ Kate Middleton / Any other wasp-y pseudo celeb type who gets regular teeth whitening treatments and is free of all body hair aside from eyebrows. All these realities can be yours (within reason). Let’s begin with a tutorial. Notepads in hand lay-dayz? Let’s begin…

The Glam Slam



You fancy huh? Everywhere you go people are jazz hands-ing behind you. Beyonce calls you for hair flipping tips. Your manicurist is on speed dial (and also may or may not be your closest confidante). Good news sophisticates, you CAN glam-or-riZee your riding boots. And here is how:

Making it Happen

Sparkles. You know them. You love them. Get out that evening shirt and take it into daylight hours with a relaxed blazer, your darkest skinny denim and a deep cognac or black riding boot. Keep things outside of the Kim Kardashian zone with the addition of cool shades and chunky scarf (obvs a cashmere blend, a gift from your manicurist…).


The No-No Pants Party


You didn’t think I’d forget about you wild ones did you? Riding can go rebel. It’s all about the mix. Oversized t-shirts get grounded by demure footing and some Wednesday Addams weekend wear can werk werk werk -what your mama gave you.

Making it Happen

First little shorts are necessary underneath. The look of a mini trapeze dress is oh-s0-sassy until a gust of wind comes by and shows-off- that-@ssy. Short bike shorts do the trick. Next power up that pout with some *super* serious colour and lastly, back it up with a mini backpack (to store your DVD of The Craft and tarot cards).

Casual Cutie




You are not as much a casual cutie as a full time babe. But compliments aside, we all know that there is something innately formal about riding boots and you might not at first glance think they’re ‘you’. Put on your imagination glasses – you know the ones- and think on this perfect look. Not stuffy at all?  No horse riding crop in sight.

Making it Happen

You need a bad daddy denim jacket . The new feel is slightly boxy, rounded shoulders are your friend. If you’re jacket has a different silhouette just practice that patented model broken-back pose. Voilà! White button down shirt; button it all the way up because collars are classy. Trouser Shorts: Suiting fabrics work best to play out this boys club look. Tweed, houndstooth – anything in a stiff wool feels fall and would make Annie Hall proud. And the top off? A wide brimmed felt hat. Don’t get crazy and try anything floppy. This is not a summer music festival.


Classic Knows Best


If I were her, I’d be grinning like the cat that got the cream too. Something is happening hur and it smells like a mix of boarding school and summers spent vacationing in Italy. Ok, lets bring it back, this little miss has done many things right but arguably the two biggest wins here are proportion and colour palette.

Making it Happen

You know how everyone is always going on and on about leggings as pants – well here is a free pass. Just this once. Bust out those leggings in neutral shades and layer under a jacket that hits BELOW the booty or conversely, like this image do a slender trouser with a cable knit sweater that hits just below the hip bone.

One detail to register is the addition of a tee under the sweater. First, it’s practical for those wooly wools but secondly, it adds a sliver of relaxed polish to that pinkies up trio of peacoat, riding boots and cable knits.

Rev Your Engine


This is back when Swiftly was curly and covered (up that is). The choice of a #TBT throw back image is no mistake; it demonstrates the timelessness of riding boots in a classic parred down basics recipe. AmIright?

Making it Happen

Jeans are key here. They must not be bulky. Save your second helpings of turkey dinner denim for another day. If your riding boots show the outline of the hem of your pants turnaround and go back home. I kid. But I also don’t kid.

Layer accordingly. Tay- Swifts has gone for a slim cut jacket and played it all kinds of safe with black on black. I am going to be bold here and say take those riding boots out of the pageant circle and bring them downtown with a leather//pleather//vegan blend jacket. Go one better by putting a slim cardi underneath for dimension.


And you’re off show ponies! Happy riding…




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