Styling Boots for Men: The Style Cheat Sheet

In the world of men’s fashion, one rule is at the top: Keep things simple. This ideology, when applied to fashion will allow you to shine, by prioritising functionality and practicality before aesthetic. The place to start? With a classic pair of boots – because with the right pair, you can stride confidently into any situation, be it the bustle of the workday, the relaxed pace of a weekend, or the intimate space of a date night.  The key is to know how to pair your boots with an outfit that projects an aura of effortless cool and subtle charm. Mix and match, play with colors, and checkout reviews from Stridewise. Nobody likes a try hard, so it’s important that your looks come across as easygoing (even if you are really researching!)  

For this style guide, we’re placing a subtle spotlight on the versatile and timeless Chelsea boot – a stylish ‘chameleon’ item that can really pull together any fit. For extra points, a pair of rustic Chelsea boots will give you a laid back vibe, whilst keeping a formal appearance due to the classic shape.

1. The Office Ensemble

Dressing for the office calls for a delicate balance between professional and cool. Striking this balance becomes a walk in the park when you bring the right pair of boots into play. Consider the classic leather boot, either in a refined black or a dark brown. Chelsea boots, with their clean lines and smart appeal, are an easy option here. Whilst they’re very formal in some ways, they also have a rich history in the music industry and don’t look out of place at the pub.

Pair these boots with well-tailored trousers or chinos in complementary colours. Add a clean, white shirt and blazer, and you’re ready to take on any business meeting or presentation. Remember to keep it simple: don’t get carried away with wild patterns or bold colours. In the world of work attire, subtlety and simplicity often communicate the most sophistication. This allows clients and co-workers to concentrate on your words and actions, rather than distracting details.

2. Date Night

On a date, everyone knows that the devil is in the detail. A meticulous, yet not over the top, look can show your date that you have style without seeming like you’re trying too hard to impress. Suede boots, perhaps in darker shades like navy or charcoal, can form the perfect base for your outfit.

Pair these with a set of dark denim jeans or smart trousers. Up top, a casual shirt or a lightweight sweater over a collared shirt can strike a balance between casual and classy. Another great look would be a black turtleneck (roll-neck). Remember, you’re going for a subtly stylish look, not a full-on costume. A dash of personal flair is good, but don’t let it overshadow your overall outfit. Adding a simple watch can be a great way to subtly communicate that you’re punctual and organised too (but please don’t make it too blingy, it doesn’t go down well).

3. The Weekender

Weekends call for outfits that are adaptable to a wide array of activities. You might be grabbing brunch at a local cafe, enjoying a stroll in the park, or catching the latest flick in the cinema. 

The Chelsea boot tends to be a reliable companion for these ventures. If you’re anything like us, you get the most out of your weekend by leaving the house fairly early and getting in quite late – so you need to make sure you have footwear that doesn’t become uncomfortable after many hours. Chelsea boots have a slip-on design using an elastic panel, which makes them easy to throw on and don’t cause your feet to become fatigued throughout the day.

Consider pairing these boots with your favourite chinos, a simple graphic or band tee, and a casual shirt worn open. If the weather calls for it, a light jacket can add an extra layer of style, we quite like the ‘coach’ style jackets, or a classic bomber jacket, or even a leather jacket in colder months. The goal is to appear casually put together, creating an impression of effortlessness.

4. The Local

You can’t beat the feeling of heading to the pub with your friends. You’re there to unwind, not stand out like a peacock. Here, your boots can bring an essential edge to your look without becoming a distraction. Opt for a rugged pair in a brown shade, these look right at home in an old-school pub or bar setting.

As usual, dark jeans or black denim is reliable here, a polo shirt or casual shirt (like a plaid pattern), and complete the look with a leather jacket or a smart jacket. Tuck in your shirt if you want to be slightly more formal.

If you’re going second-hand on the leather jacket, you can get some good deals – but be careful that you don’t pick up one that has a short shelf life. A bit of wear and tear looks authentic but there’s a balance to it. Dark greens go great with brown leather, so consider this colour if you’re wearing a hat, or even for your socks!

Some Useful Style Don’ts

While fashion is often a platform for self-expression, there are a few potential pitfalls to sidestep when styling boots. For starters, avoid overly clashing patterns and bright, flashy colours. Secondly, don’t overlook the upkeep of your boots. Keep them clean and well-maintained; scuffed or dusty boots can detract from your overall look. It’s also important to wear them occasionally, as it’s not good for boots to be sat in storage for multiple months on end. Lastly, remember that the objective isn’t to draw all attention to yourself, unless it’s very intentional. As in many areas in life, subtlety in fashion goes a very long way.

Another important tip that we’d like to stress – don’t worry about only having a few outfits that you wear often. Whilst having new clothing is appealing to our nature, it’s not efficient for your finances or the environment. It’s nice to have some trusty clothing and footwear items that are reliable, and these become part of your ‘look’ over time. When buying new pieces all of the time, there is a lot of unknowns and room for error, such as things not matching, being comfortable, or not fitting right. Saying that, it’s important to leave the door open for new ideas and looks – but just keep an eye on your spending.

You may notice that streetwear isn’t really emphasised in this article – whilst we appreciate the style, generally this should be reserved for very informal occasions unless you know your way around this style well. Streetwear is an art in itself, and to pull it off properly, we suggest immersing yourself into various subcultures, such as skating, music and art – because this is where the most relevant streetwear emerges from. When building your style, we suggest starting with the basics and going from there.

You can find more fashion don’ts here

General Grooming Tips

Apart from your outfit, remember that general grooming really contributes to the overall impression you make. Whilst some of these tips may be obvious to some, it can be easy to drop the ball if you’ve had a busy few days or running to an event straight after work. 

Here are some essential grooming tips:

• Facial Hair: Keep it neat and trimmed. A well-maintained beard or a cleanly shaven face can enhance your look. If in doubt, just take the beard down to stubble with an electric razor, rather than clean shaven. We also recommend keeping a bit of sideburn, but not too long.
• Eyebrows: Tweeze your unibrow to keep it in check. Never shave it – this can lead to stubble that detracts from a neat appearance and can also get itchy.
• Aftershave: A subtle dash of aftershave can make a world of difference. Remember, the goal is to lightly fragrance your skin, not overpower the room. You can also pick up scented post-shaving balms/moisturisers.
• Deodorant: No outfit is complete without a good application of deodorant. It’s the invisible part of your grooming routine that can make a massive difference in your personal presentation. Make sure it’s an anti-perspirant and not just body spray.
• Comfort: Ensure your clothes fit you comfortably. It’s hard to look confident and relaxed when your clothing is making you anxious or uncomfortable.

Style Only Goes So Far

Remember that your outfit can indeed make a statement about you, the true essence of your personality radiates through elements that transcend the physical – your body language, the quality of your conversation, and the confidence you project.

Now, this isn’t to say that what you wear doesn’t matter at all. It certainly does. Your clothes can boost your confidence, make you feel good about yourself, and subtly convey your personal style. However, clothes should be seen as an enhancement, not the main part of your image.

When putting effort into selecting your clothes, make sure that you also work on essential aspects of your personality. They could make a far more significant impact on your image than your wardrobe could ever hope to. We often see popular men who are chatting away with friends and on dates – who clearly don’t invest heavily in their style, but their strong personality over powers that aspect and people don’t even notice.

Whether you’re preparing for a busy day at work, getting ready for a first date, or just heading out to the pub – a pair of Chelsea boots is a trusty option to carry you through it, giving you a strong foundation to build on further.

We’ve also considered what personal style means and how it transcends appearances through personality. The way we carry ourselves, how we interact with others, and the level of confidence we have all play a role in projecting an overall image. Good luck out there and have fun with your style!