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5 Casual Rainy Day Outfit Ideas to Keep Dry, Snug and Stylish

18 Feb 2025 |

If there’s any style we know how to do, it’s rainy day style. With our range of waterproof jackets, leather boots and knitwear, we love cosy but practical clothing. That doesn’t mean you have to sacrifice style, it’s all about the small finishing touches to an outfit and wearing shades, patterns and pieces that complement each other. That’s why we’ve selected 5 casual rainy day outfit ideas to keep you dry, snug and stylish.

Ribbed jumper, dark wash jeans, leather Chelsea boots & bomber jacket

If you’re looking for a cosy outfit that’s dressy enough to wear for a meal out with friends or family, it’s this one. A ribbed jumper in your favourite colour, whether it’s a V-neck, a half-zip or a crew neck, will become your go-to jumper during the colder months. For men, a half-zip shooting jumper is the perfect neutral option and it’s such high-quality wool too. Our crew neck and V-neck ribbed jumpers for ladies come in a gorgeous array of country colours too.

If you’re opting for a colourful jumper, keep the rest of your outfit neutral. A pair of dark wash slim leg or straight jeans looks flattering on everyone and the dark wash elongates your legs too. Paired with some leather boots, you’ll stay dry on your bottom half. Whilst we love suede boots and you can protect them from rain, we recommend sticking to regular or patent leather.

Finish off the look with a bomber jacket in a neutral colour for a classic casual country outfit. If it’s really cold outside, we recommend investing in a fleece-lined bomber jacket but with a ribbed jumper underneath, you should be warm enough.

Collared shirt, fleece jacket or gilet, chinos, brogues & wax jacket

If you’re looking for an outfit that’s a little smarter, this formula will be perfect for dressier occasions. A collared shirt should be a staple in any country gentleman or lady’s wardrobe. Most of our customers have a variety to pick from, from neutral shades to brighter colours, from checked patterns to subtle country animal prints, we have an extensive range.

An item that pairs well with a collared shirt is a fleece jacket or gilet. Our Harpham and Huggate styles for both men and women are some of our most popular designs. We love them so much that we have multiple styles. There’s a gilet version, a half-zip style or the full-zip jacket to give you options as a mid-layer piece.

Of course, you could wear this look with dark-wash jeans again but we love switching out our jeans for chinos. They’re a tad smarter so they’re perfect for a dressier event whether you opt for a light beige colour or a darker olive pair.

When it comes to footwear, the smarter, the better. A pair of leather brogues should be your go-to smart option of shoes and provided you keep them clean, they should last you for years. We love a tan-coloured pair as they go with most pairs of trousers but you could opt for a pair in chocolate brown instead.

Your jacket of choice should also be smart and a wax jacket fits the bill. It’s showerproof enough for walking to a restaurant or venue although we wouldn’t recommend going hiking in such a jacket! Again, it needs to be protected regularly so make sure to clean and care for it properly.

Long-sleeved rugby shirt, chinos or jeans, market boots & changing robe coat

For a more casual day-to-day outfit, this is a perfect ‘running errands’ ensemble. A rugby shirt is such a comfortable item to wear and because of the thick cotton material, it feels like a jumper at times. We love wearing a rugby shirt to add a splash of colour to an outfit too.

Again, a rugby shirt can be paired with just about any trousers, from joggers if you’re lounging around at home to jeans or chinos if you’re heading out of the door. It looks best with darker trousers so the colour of the shirt contrasts against it and stands out.

For a casual look, a pair of leather market boots with a sturdy, thicker tread are perfect for running errands, especially when it’s wet and muddy out. You might be grateful for the extra grip if it’s slippery outside during the winter months.

To finish off the look, a changing robe is the perfect item to complement a casual outfit. The fleece or towelling lining keeps you warm without adding a bulky layer underneath and is super practical. The longer length will keep your entire body dry too and it’s one of our favourite coats to throw on when we’re heading out of the door in a rush, especially if you have children!

Thick knit jumper, slim fit jeans, wellies & jacket in a packet

If it’s colder outside, you might want to wear a thicker layer underneath your jacket. A thick knit jumper, whether it’s a cable knit or a shooting jumper, will keep you warm during the winter. You could even add a thermal or plain T-shirt underneath if it’s below freezing temperatures!

We love our slim fitting jeans! Again, they’re flattering on every body shape for both men and women so we had to include them again. Skinny jeans may come in and out of fashion but a slim fit style remains a classic. Again, you can opt for a dark wash but we also love a mid-blue hue.

You’ll need slim fitting jeans to fit inside your wellington boots on a rainy day. Tuck them inside and stick on a pair of boot or thermal socks to keep your feet toasty warm. Wellies fit a little looser so by tucking in your jeans, they should fit better around the calves.

Because you have a thicker layer underneath, you might be able to wear a more lightweight jacket on top. A jacket in a packet is an essential that we recommend all country folk have stored in their wardrobe, car or rucksack at all times.

Thermal top, walking trousers, walking boots & hiking or walking jacket

Casual rainy days don’t have to mean that you stay indoors. In fact, a light shower when hiking or walking can be refreshing! With that being said, you still need to layer up as the temperature can change quickly. A thermal top as your first layer is a necessity for any walk.

On your bottom half, you might want to add a pair of waterproof walking trousers on top of a pair of leggings or trousers if it’s a downpour. We’ve improved our fit over the years so they now have a straight leg with an elasticated waist.

If there are any shoes that every country-living person should have, it’s a pair of walking boots. You’ll get plenty of wear out of them even if the only walking you do is taking your dog for a daily walk. They have great tread for uneven terrain and as long as you get rid of the mud after every wear, they’ll last years.

Finish off the look with a waterproof walking jacket. These jackets have been designed for the activity, with a foldaway hood, plenty of pockets and stormproof cuffs. We wear ours on a daily basis instead of just for walking too!

You’ll notice that many of these outfit formulas can be switched out for other items, including any of the above. We’re big believers in having a wardrobe that you can mix and match without having to think if certain items go with another. A neutral colour palette, plenty of layers and well-fitting items make for the perfect country wardrobe.

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