Chelsea boots are a boot style that seems to stay in fashion, year in, and year out. This makes them a great choice of boots that you can rely on throughout all the seasons if you need a go-to pair of boots.
One of the questions that people often ask is how they can best style Chelsea boots and what clothing goes well with them. Since the Chelsea boot is a classic shoe, we find that they are easy to style and can go with a wide range of clothing types, from suits to casual. With that in mind, we have put together some outfit ideas and occasions that we think will go great with Blundstone Chelsea Boots.
The first thing to note is that not all Chelsea boots are the same and we offer a range of different types of boots from Dress Series to All-Terrain Series. So, your choice of Chelsea boot may well dictate what you are going to be wearing. Our Original and Classic styles are very flexible and can be used as a great all-round boot if you need something that you can use for different situations. While you can easily wear Chelsea boots in the summer and all year round, they are also perfect for use in the winter.
Chelsea boots have always been a great choice for winter footwear, offering both style and functionality. In fact, for many people, Chelsea boots are their first-choice boot when the weather turns cold. Chelsea boots are also great for wearing in winter because they can easily handle inclement weather conditions. Leather as a material is weather resistant to both the rain and the snow, so your feet should remain dry. Leather doesn’t offer the same protection as specialist rain boots or snow boots, but Chelsea boots can generally cope with normal winter conditions that you might encounter in every day.
Need waterproof* boots and like the look of Chelsea boots? Blundstone’s range of men’s waterproof* Chelsea boots and for women are the perfect option.


Chelsea Boot Color Options
The color of the boot will also have an impact on what you might want to wear with it. The great news is that Blundstone boots come in a variety of colors, shades, and styling options.
Traditionally, stout brown boots are more likely worn with casual clothing and less formal outfits whereas black boots can also be (but not necessarily) used in more formal situations. However, fashion and style can also be about breaking the rules and pushing the boundaries.
Lighter brown boots such as tobacco or Sierra brown work well with jeans and casual wear. If you like to make a statement with your feet, then another great option is to try something other than brown or black boots. Some great choices for alternate colors include dark olive, steel grey, and pearl white.
If you like black or brown boots but want a pop of color then consider boots that feature a distinctive color or stripped elastic gusset, as these can create an interesting and stylish statement.
Another option is to pick from our range of waxed suede Chelsea boots. These will look great on your feet and are even water resistant, so you don’t have to worry about getting your suede boots all messed up in the winter climate.
Chelsea Boots for Casual Looks
Chelsea boots offer both versatility and style as a winter fashion accessory. They are a great addition to any winter outfit. They can be paired with various outfits to create looks ranging from casual to dressy. This means Chelsea boots can be worn all day long, from going to work, to then socializing around town to the evening.
For a cozy yet stylish look, pairing Chelsea boots with a chunky sweater is an excellent choice for the winter. For a laid-back winter style, Chelsea boots are perfect for jeans or leggings. For a slightly smarter look, a cashmere or fine knit sweater or cardigan will be a great combo with trousers and a pair of Chelsea boots.
Women who want a stylish look in the winter can wear Chelsea boots with woolen tights and dresses or even skinny jeans. Yes- skinny jeans are making a return (for women at least) and are popular again.
Men can wear Chelsea Boots with straight-leg jeans or bootcut jeans as this is a great look. On warmer winter days or in the fall, chinos or cotton trousers are another option. A beanie, puffer jacket, and a pair of Chelsea boots are a great, classic look that will keep you warm.
For women, when wearing jeans, consider rolling the hem slightly so it sits just above the boot. With a great pair of Chelsea boots, you want to ensure that everyone can see them properly. This small detail will help show off your boots, and if you’re wearing winter socks, you can include a pop of color to make a bold statement.
Layering is key to staying warm and stylish during winter. You need to select the right clothing that will keep you warm whilst still looking the part and remaining stylish. Just because it is cold, it doesn’t mean you can’t look good at the same time.
For a dressier look, Chelsea boots can be worn with a sweater dress and tights. Black tights, in particular, work well with Chelsea boots but you can get creative with your choice. An over-the-knee dress and ankle booties is a classic look that seems never to go out of style.
Women who fancy something a little different might like our boots with a lug sole.


Evening Wear
One of the great things about Chelsea boots is that they can easily transition from casual to more formal evening wear. You can wear Chelsea boots to a wide range of engagements, from restaurants, and bars to clubs and late-night venues. In the instances where you may want to avoid sneakers because they are not smart enough, but you want something robust on your feet to cope with the winter weather, a pair of Chelsea boots fit this role perfectly.
Women can wear Chelsea boots in the evening with smart trousers, leggings, or tailored jeans. A smart midi dress also works well with boots. In the winter, one of the big concerns is how to stay warm. One stylish option for women is a faux fur coat or even a shearling jacket which will look great in the evening, plus can keep you warm.
For men, a suit, blazer, smart shirt, or turtleneck jumper works great with a pair of Chelsea boots. If you need a smart coat to keep warm, then think about an overcoat. This works great for business wear too.


Winter Boots for Business
If you’re looking for a pair of boots for the office, then Chelsea boots make for a stylish accompaniment to a suit or smart casual business outfit.
Our standard Blundstone boots can easily transition into business casual attire for men or women. However, if you’re looking for something a little bit more business-orientated then our dress boot range for men and heeled dress boots for women are great options.
Chelsea boots are great for work as they can help create a refined and elegant appearance, perfect for day-to-day work or business meetings.
When it comes to style tips, the current trend for men’s suits is for them to be slim-fitted and tailored. This works great with smart Chelsea boots. For those who prefer a more relaxing fit to their suit, again, Chelsea boots will work with this trouser cut and silhouette, even better news, this look is starting to make a comeback.
For men, a navy suit goes well with brown Chelsea boots, whereas a charcoal suit works better with black leather boots. Fancy something a little different? Blundstone also offers a range of lace-up boots that are great for work wear.
A Note on the Right Socks
The choice of socks plays a crucial role in completing a Chelsea boot outfit. While you can wear socks of the same color as your boot to create a seamless look, you can also pick a pair of socks that add a contrasting color to your outfit.
Comfort and performance are other key factors when picking socks, especially in the winter when it can be a little colder. In colder temperatures, you want to wear a pair of socks that will keep your feet warm. You also want a material that will let your feet breathe.
It’s also worth getting socks that will be long enough to go over the top of the boot as socks that are too short can be uncomfortable to wear in boots. The exception here is for women who may want to wear tights with their boots, and typically a shorter sock that sits inside the boot will be worn for comfort and to keep the feet warmer in the colder weather.
If you’re wearing boots to the office with a business suit for instance, you should skip the boot socks and go with dress socks for a more stylish, and in-keeping look. However, dress socks are thinner in size than boot socks so they may alter the fit of the boot. For individuals with wide feet, a dress sock can be the solution to a fitment problem in some boots. So, it is worth considering this as an option if this is the case with your own feet.
With this in mind, whilst you can wear whatever socks you like, it might be best to consider how you are predominately going to wear your boots. If you’re going to be leading an active lifestyle and you want a pair of boots that you can wear in a range of different situations, then fit them to go with boot socks. If you are going to be wearing them in an office situation or where you will be dressing up more often, then consider fitting them with dress socks.
Regardless of your sock choice, if you’re looking for a pair of boots to wear in the winter-time, then a pair of Chelsea boots is a great choice.


From leather boots to suede boots and more, buy winter boots for your style with Blundstone today.
* Leathers referred to as waterproof are routinely tested for resistance to water penetration up to 12,000 / 15,000 flexes using one of the following SATRA test methods: TM171 using SATRA STM703 Bally penetrometer (or equivalent) or TM34 using SATRA STM606D Maeser type WR tester (or equivalent).