I Just Tried on the Best Cowboy Boots, and They're Surprisingly Easy to Style

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I don’t need to tell you cowboy boots are back (that’s old news now). However, you might be wondering how to wear them. Who would have thought we’d see the return of the Western silhouette? We last saw these boots sometime in the ’90s when we obsessed over how Victoria Beckham wore them to England matches. Then we watched Britney Spears perform in a pair with denim cutoffs and a diamanté choker. But this season, they’ve undergone a high-fashion makeover all thanks to the likes of Calvin Klein, Maison Margiela and Fendi (to name a few).

As a stylist, I’m obsessed with the style and want to pair them with quite literally everything. But when autumn started to approach, I was unsure whether I could actually wear this trend myself. I find boots really hard to buy because of that awkward “jeans hitting boots” situation. So it was time to stop browsing and start trying on all the new cowboy boots catching my eye. Cue lots of shoehorns and changing-room stress. Keep scrolling to see and shop my guide to wearing cowboy boots this autumn.

1. Cowboy boots with jeans

On Hannah Lewis: Joshua Millard Rapshaw Patchwork Jacket (£450); Warehouse Slim High Rise Jeans (£46)

First up, I wanted to find a great high-street style that actually looks expensive (who doesn’t?) and that I could wear with my everyday clothes. I am no good with heels, as I am on my feet all day, so that had to be factored in. Enter Mango’s ankle cowboy boots. They’re a great shape to pull on and don’t go too far up your leg, meaning they sit perfectly with jeans. The hardest decision with these is whether to go for them in black or white.

2. Cowboy boots with a summer dress (I'm still holding on)

On Hannah Lewis: Sleeper Briditte Polka Dot Linen Dress (£171)

I loved these so much that I’ve even used them to hold onto my summer dresses for as long as possible. Team gorgeous cotton dresses and silky slips with a pair of knee-high Western boots (maybe even throw on a knit over the top) and you can hang onto your summer wardrobe for another month at least.

3. Cowboy Boots for the evening

On Hannah Lewis: Zara Snake Print Jeans (£40) Staud Beaded Drawstring Bag (£259)

Since cowboy boots aren’t the most glamorous shoes, it’s hard to feel dressed up for the evening with them. Except for these Magda Butrym pointed booties. Made with luxe black suede leather, super-high heels and clip-on pearl embellished broaches, these boots add that much-needed touch of playfulness.

4. Print Paired with Print

On Hannah Lewis: Rains Glossed PU Trench Coat (£160); Staud Bissett Croc Effect Bucket Bag (£310)

As we all know, animal print is quite literally everywhere right now. Yes, a pair of cowboy boots is a great way to subtly opt into the snake print trend, but what’s even better is to wear them with even more animal print. I wore my snake-print Zara boots (I love their square-shaped toe) with my favourite pair of snake-print jeans. You will want to keep the rest of your look low-key here. Go for a plain white tee on top.

5. Knee-Highs Worn Under Dresses

On Hannah Lewis: Gestuz Aya Long Shirt (£289); Mango Beaded Bag (£40)

Even though I felt utterly ridiculous, I was dying to try on a seriously Western pair of knee-high cowboy boots, and Topshop had just the affordable pair I was looking for. Complete with all the trimmings (buckles and even a faux spur on the heel), I found the best way to style these was with a calf-length dress. Bonus points for shirtdresses or those with a slit, as then the boots can really be shown off.

6. Use Cowboy Boots to Refresh the Skirt-and-Jumper Combo

On Hannah Lewis: Arket Alpaca Blend Knitted Tunic (£79); Preen by Thornton Bregazzi Asymmetric Floral Print Devor Skirt (£425)

I’m such a sucker for silk skirts and chunky knits. Especially over fashion weeks, these two pieces are my go-tos to feel comfortable for both the day and evening. The way to give this a 2018 spin is with a pair of cowboy boots. With a skirt, you can go for a higher boot such as this Topshop Marcel pair. Their contrasting red wooden heel and croc-effect leather gives them a stronger Western feel.

Top Tip: I found that going up a size in each of these styles stopped me from battling through the first few weeks of breaking them in. 

Shop More Cowboy Boots

They say you shouldn’t have favourites, but these are mine. Perfect in every way.

The croc-effect white leather with black topstitching make these look so expensive. 

Fendi has included all the elements, and it just works so well.

This shoe-boot hybrid is a great middle ground to introduce yourself to the trend if you’re worried about where the boot will stop on your leg. 

Next up, see all the key autumn/winter 2018 trends.

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