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What to Wear With Brown Boots

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You won’t find a more versatile pair of footwear than a pair of brown boots. For both country ladies and gentlemen, they are so easy to dress up and down without too many changes. Of course, it will depend on the style of boots you have but as always, we love to mix and match here at Rydale and we aim to make the most out of what you have already. It’s only then do we recommend adding in a couple of key pieces to really elevate your look.

If they’re not already, brown boots should be a staple in your wardrobe. You’ll soon see just how versatile they are, from outfits to weather, from lifestyle to occasion. Black and tan boots both work wonders but there’s something special about brown boots that seems to go with everything. In this post, we’ll share our favourite types of brown boots for both ladies and men along with our usual country styling tips. Your outfit will look amazing whether you’re at the shops, spending the night indoors or walking the dog!

ladies leather Chelsea boots

Country ladies

Brown boots are seen in every single high street shop as soon as the autumn/winter collections start appearing. However, they will do you all year round because how many days a year really do we have to wear sandals in the UK? However, different boot styles can require just a small adjustment to an outfit. Also, some styles are more daytime than night-time options so it’s definitely worth bearing that in mind if you are thinking of buying a new pair!

Ladies suede Chelsea boots

Chelsea boots - leather

The classic leather Chelsea boot is the go-to pair for day or night. With its streamline and sleek look, it’s smart enough for evening occasions as well as day trips or running errands. We don’t recommend them on long-distance walks or on rough terrain though; they have enough grip for everyday walks but not for woodland.

Our staple item to wear with leather Chelsea boots has to be skinny jeans. The classic indigo or black skinny jeans will never go out of style but equally, khaki, beige or even light pink pop against brown Chelsea boots. Pair your skinny jeans with a checked shirt and tweed blazer for a night at the pub. For more casual trips, switch the blazer for a gilet and stick on a cable knit jumper on cooler days. 

Ladies Spanish riding boots

Chelsea boots - suede

Brown suede Chelsea boots are perfect for drier days so they don’t require as much cleaning! This is a style you can wear with skirts and dresses too as dark brown suede elongates your leg when worn with dark tights too.

A pair of suede brown boots are the perfect outfit finisher for a tweed skirt. Because the shoes are dark, it allows the skirt to show itself off! Finish off the look with a thinly knitted jumper for a cosy but smart-casual outfit. Add a patterned country shirt underneath if it’s extra cold!

Biker boots 

The most casual of the boot styles, biker boots are designed for rainy days and rough terrain. They tend to have the best tread on the soles to handle uneven paths when out walking. However, that doesn’t mean they can’t be a stylish addition to any outfit.

The trick here is to tuck in any trousers: jeans, jodhpurs and leggings. They need to be slim-fitting so skinny jeans are the best of any type of jeans. Again, we tend to stick with classic shades: indigo, black, beige and khaki. However, if you want to rock a patterned pair of leggings, go for it! You can even wear long boot socks or knee-high socks over your leggings/jodhpurs/skinny jeans and show off the tops of them. Who doesn’t love a bright sock?

To round off this look, we love a classic leather jacket, which is the ultimate cool girl piece. If you want to mix up colours and wear a black leather jacket with brown leather boots, this is the outfit to do it. It’s all about making rocker chic into country chic! 

Men's Leather Chelsea Boots

Knee-length riding boots

Knee-high boots can be tough to pull off but the main thing to be aware of is wear thin trousers. Just like biker boots above, leggings and jodhpurs fit perfectly but if the calf is wider, skinny jeans should tuck in also. If you will be tucking in trousers, consider buying a regular fit as opposed to a slim fit boot. 

No longer do riding boots have to just be worn at the stables, you can wear them out and about too meaning maximum value and wear for money! There’s something about clean, knee high boots that always looks so put-together. 

If you’re not a fan of trousers, fitted skirts work just as well with riding boots. Tuck in your checked shirt and finish off the look with a tweed blazer or jacket and you’re ready for a meal out with friends or family or even a smart-casual party!

Mens Brogue Boots

Lace-up brogue boots

Our brogue boots are a cross between our brogue shoes and a pair of leather Chelsea boots. They’re a more formal version of Chelsea boots but keep your ankles warm too, unlike shoes. They tend to have more decoration on them than traditional Chelsea boots, lifting them to a dressier look.

If you want to dress them down, skinny jeans wouldn’t look out of place with them. We would stick with darker, classic shades, such as indigo and black, to keep with the dressy feel of the boots. A checked shirt compliments a dressy boot so tuck it into your jeans, throw on a leather belt and add a tweed blazer on top. This is the ultimate countryside lady look, perfect for casual events where you want to dress up a little. 

Country gentlemen

A classic pair of brown boots will see you through every season, even summer, so you need to have a think about what sort of occasions you’ll be wearing them for. If they’re more for socialising, a shorter, ankle length style will work best. If you know you’ll be on the farm or walking in the woods or on the fields a lot, a pair of knee-high boots would be more suited to you. 

Mens pull on work boots

Chelsea boots - leather

If you’re looking for a versatile, everyday boot, a Chelsea boot will do the trick. Wear them for casual events, smart-casual occasions, the office even! The trick is to keep them clean so make sure you give them a quick wipe after every wear. Nothing spoils an outfit like dirty or untidy shoes!

Your go-to item to wear with Chelsea boots is always straight leg jeans in a dark wash. Darker colours on your bottom half give a smarter look than light colours but that also means you can add some colour to your top half if you want to. Simple crew-neck T-shirts add a casual edge to the look or a checked shirt gives it a more smart-casual look. Don’t forget your wax cotton jacket to wear on top too. 

Lace-up brogue boots

Your dressier version of the Chelsea boot is the lace-up brogue boot. Here, you can go for the smart-casual look even more. They’re perfect for dressy winter occasions to keep your feet a little warmer than traditional brogues can. 

We’re big fans of wearing brogues with tweed suits so that could be one option for you. If that feels a little formal for you, how about keeping the blazer or waistcoat and wearing a pair of chinos instead? Stick on your checked shirt underneath and you’re ready for any party or event.

Worker boots

Worker boots are essentially Chelsea boots but with a thicker tread. This makes them perfect for outdoor activities such as walking or working on the farm. They’re easy to slip on too, like Chelsea boots, so keep them by the door for any emergency outings!

Whilst you can wear them with outdoor workwear, you could also wear them when out walking in the outdoors. Again, straight leg jeans should be a staple in your wardrobe and worker boots go just as well as any other footwear does with them. You might prefer something more casual on top so why not try a rugby or polo shirt and throw on any jacket you wish? 

Mens tall leather boots

Knee-high leather boots

If you’re going to be predominantly working outdoors, you need to invest in a pair of knee high leather boots. This type of boot has the best tread of all as they are designed to worn when working on fields. 

You can go for a traditional country look with a pair of breeks, which are often easier to tuck in than other types of trousers. You’ll need a waterproof layer on top of any outfit but wear whatever feels comfortable to work in underneath.

As you can see from above, brown boots should be a staple for any country lady or gentlemen if they’re not already. Black boots can sometimes be trickier to wear, especially when it’s not winter, and brown boots add a warmth to any outfit. Whether you prefer an ankle boot or a knee-length style, there really is a style for just about anyone!

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