A great outfit starts from the ground up. People, especially women, tend to notice your shoes first, and the right pair of boots can make an especially good first impression. They can express your personality through a variety of styles (rugged, refined, classic, etc…), as well as fit a wide range of casual or dressier outfits. Chinos are similar in this regard. They also fit a wide variety of styles, and can work for casual or dressier situations. With this in mind, pairing boots with chinos is not only a great stylistic match, but this combo also opens up a ton of possibilities for your wardrobe.
Even though this pairing makes stylistic sense, you should see it more. Most of the time men will wear sneakers to dress down a pair of chinos, or they’ll wear loafers or dressier shoes (bluchers, derbies, and even oxfords) to dress it up. Boots hit the sweet spot right in the middle of these two stylistic directions.
This combo will also help you stand out in a subtle way, since you don’t see it all that often. The versatility of each item provides the foundation for a wide range of outfits, but most importantly, the combination almost always looks sharp without being too stuffy.
| Category | Brand | Best Features |
| Best Classic Casual Boots | Clark’s Desert Boots | Supreme comfort and casual appeal |
| Best Rugged Casual Boots | Red Wing Weekender Chukka | Surprisingly versatile, incredibly durable |
| Best Dress Boots | Beckett Simonon Preston Chelsea Boots | Sleek and polished, not too stuffy |
| Best Sneaker Hybrid Boot | Jack Erwin Reade Boots | Comfortable but not too sporty looking |
| Best Splurge Boots | Rancourt Byron Boot | Top quality looks, construction, and durability |
Why you should wear boots with chinos
We’ve already mentioned the two major reasons to sport boots with chinos – the versatility and the ability to balance a sharp yet relaxed vibe.
But there are other important reasons too. Because of the wide variety of boots available for any type of style, boots allow you to express your individuality and confidence. We love all shoes styles, but the variability of boots is unmatched. Other shoe styles don’t have as much variety in style, which can limit the ability to express your personality or take stylistic risks.
If your style leans refined or dressier, a cleaner pair of Chelsea or dress boots looks great with so many outfits. For those who prefer a more rugged style, you can go with any number of more active or workwear inspired casual boots. And those who tend to wear more middle-of-the-road casual clothes might find a pair of suede or leather chukka boots, like a classic pair of Clarks Desert Boots, to fit their needs. The pictures below show how well all of these can match different types of chinos.
Benefits of the combination
Most men traditionally pair boots with jeans. While this classic combination does work well, stepping up the dressiness level of the pants one notch to chinos will open up so many more potential combinations. For instance, boots, jeans, and a t-shirt is a well-worn combination and looks great. However, swap in some chinos, and you elevate the outfit just a little bit. Jeans are great and will always have their place, but they don’t quite offer this level of versatility as they are harder to dress up.
While dress boots and slacks can create a dynamite combo for dressier situations, chinos and boots will cover more ground on the casual side. Because chinos are a touch more casual than slacks, more varieties of boots will pair better with this piece.
This combination also allows you to dress with more color. The wider variety of chino colors will give you more color options for your entire outfit. Khaki, navy, olive green, off-white, etc… will open up so many different color possibilities for whatever look you choose for the day.
You can also keep your style more consistent across seasons. Boots with chinos can work in many different weather scenarios. When it cools off, you can wear chinos made of heavier winter fabrics (thicker cotton and wool blends, or flannel lined chinos). As it heats up, you can swap in lighter fabric chinos (lightweight cotton or linen blends) to keep cool. And while some boots are better than others for specific weather conditions, most are versatile enough to work with warmer or cooler weather. Defaulting to this combination for your lower body attire allows you to keep a certain consistency across the seasons.
Matching with shirts and outerwear
The most fun part of the boots with chinos combo is experimenting with different shirt and jacket combinations to match your boots and chinos. With this basic set up for your shoes and pants, you can go the extra step in expressing your personality. The pictures below offer a few good ideas of how to work from this foundation. Notice how the different style types all work well with this pairing.
How to best sport this look
While both items are known for their versatility, it can be easy to get boots with chinos wrong. The three keys below will help you execute this look for a sharp, relaxed vibe.
Well-fitting pants
Well-fitted pants will make or break this look. In general, you want your pants to give your legs shape and structure without restricting your mobility and comfort.
Pants that are too baggy or too long will drown your legs and give off a sloppy appearance. Chinos that are too tight will limit your movement and comfort, and the pulling of the fabric will look restrictive and uncomfortable. Even if you have muscular legs and wear stretchy chinos, the overly tight styles will take away from the cool and relaxed vibe that chinos should give off.
Fit guidelines
Your pants should skim your legs without restricting your movement. There should be a slight taper to give your legs some shape. The length should stop right where the pants hit your shoes, with maybe a single break. Perfectly fitted chinos will give off a polished and tailored look, while keeping the relaxed casual vibe of the chinos. Combining a refined look with a relaxed garment will hit the sweet spot for a smart casual look.
For those of you who prefer fuller pant styles, this can work well with boots too. Just make sure there is a visible taper to give your legs some shape, and that the length is just right. With these fuller cuts, if your pants are just a little too long, you can get that pooling of fabric around your ankles that does not flatter your leg shape.
| Category | Brand | Best Features |
| Best Overall Chinos | Bonobos 2.0 Chinos | Perfect fit and variety of fits 4-way stretch chino fabric |
| Best Budget Chinos | Gap Modern Khakis | Very good price (often on sale) Good performance fabric |
| Best Mid-range Chinos | Banana Republic Traveler Pant (when on sale) | Stretch fabric that isn’t too tech-y Comfortable yet sleek |
| Best Splurge Chinos | Proper Cloth DiSandro Stretch Chinos | Top of the line Japanese fabric Great drape and texture |
Work off of your personal style
As with any outfit, try to stick with pieces within your stylistic comfort zone. Choosing pieces that fit your personality will create more confidence, which is the key element that makes any outfit more than the sum of its parts.
If you tend to dress more casually, like wearing jeans and a t-shirt most of the time, an overly dressy pair of chinos might throw you too far out of your comfort zone. A good start would be a pair of more casual chinos or five-pocket pants in a neutral color (brown, grey, navy, beige/khaki).
If you already wear chinos quite often, you can experiment with different colors or fabrics out of your typical comfort zone For instance, if you always wear khaki, grey, and navy, try some in olive, stone, or dark brown.
If you tend to dress up quite a bit, you can pick a more standard pair of cotton chinos to relax your look for more casual situations.
The variety of chinos available gives you a ton of room to find a look that works best for you. Check out this article for more advice on pairing chinos with shirts.
Boot variations
This concept applies to your boots too. If you’re not sure what boots will work best, try to find some that match your personal style first. See the examples below for some inspiration.
If you tend to dress more ruggedly, a pair or workwear or sportier (but not too technical) boots will work great. Those who tend to dress more standard casual (jeans, t-shirts, button-downs) will find a great variety of boots, with the Clarks Desert Boots as the easiest choice (along with other similar chukka boots).
For the dressier guys, dress or Chelsea boots work just as well with your tailored attire (suits, trousers) as they do with chinos. Matching dress boots with chinos provides a sharp casual look that tones everything down just a bit to keep the vibe more relaxed and comfortable. I like this combination for relaxed social situations – a casual drink, dinner with friends, or a date.
Color combinations
Dark and medium brown boots are usually a safe bet. They match all neutral colored chinos, and most bolder colors as well (burgundy/red, different shades of green, bright blue, white, yellow, etc…).
Black boots can go well with black or darker grey chinos.
While less versatile, grey, olive, or lighter brown boots can work wonderfully with chinos too – usually as a good way to mix in something bolder or unexpected with neutral colored pants. Other bolder colored boots can work, but it’s harder to pull these styles off without going too over the top.
Below are a few examples of chino and boot color combinations:
- Standard: brown boots, khaki/grey/navy chinos, bold or neutral colored top
- Bold – Spring: medium brown boots, bright blue/red/sage green/yellow chinos, neutral colored top
- Bold – Fall: dark brown/dark grey boots, brown/olive/burgundy/mustard chinos, neutral colored top, dark outerwear/jacket
- Fun – Summer: tan/light brown suede chukka boots, white/pale grey chinos, bold colored or patterned top
- Business casual: dark brown dress boots, navy/dark grey dress chinos, white/light blue button down
If you’re looking for more ideas on what to wear with chinos, check out this article.
Don’t overthink it
Despite all of the nuances we’ve covered with this look, the biggest key is to keep it relaxed and not overthink things to try to make everything absolutely perfect. The charm of the wearing boots with chinos comes from combining two pieces that don’t need much consideration to match, and then being able to easily throw on other parts of your outfit.
If your pants fit well and your boots reflect your personal style, throw the two together, find a matching top, and get on with your day. This is the real benefit of the look – it gives you one less thing to think about.
FAQ
Yes, you can wear chinos with boots. Boots with chinos offer both a relaxed casual vibe and can fit a variety of social situations. Given the wide variety of boot types available, as well as the varying degrees of casual and dressy chinos, you can rely on this combo to look good and fit many different scenarios.
Many different types of pants go well with boots. While anything from jeans to dress slacks can match different types of boots, chinos are the perfect middle ground to match most boot styles. For casual or workwear-style boots, you can stick with more casual chino styles. With dressier boots, go with chinos that look closer to dress slacks in their details – this gives you a great smart casual foundation that works with polo shirts and dress shirts.
The biggest benefit of wearing boots with chinos are the versatility of each item, how you can stand out in a subtle way, and the ability to look sharp yet relaxed. Because this combo is not seen as often as others, people will notice. And the versatility of each item provides the foundation for a wide range of outfits.
You can absolutely wear Chelsea boots with chinos. This combo usually works well with more refined attire. You should pair these with a dressier pair of chinos, and the rest of your outfit can range anywhere from smart casual to dressy. Think dressier knit polo shirts, button downs, and even a casual sport coat.
There is no one style of boots that are the best to wear with chinos, which is why this look works so well for so many. Since boots and chinos are both versatile pieces, you can match different types of boots with different types of chinos depending on your personal style and how dressy you want your outfit to look. The only thing to avoid is too much contrast between the dressiness of each item, which can create an inconsistent look. For instance, you want to avoid a combo like workwear or active boots with dressier chinos, or dressy Chelsea boots with rugged canvas chinos.
Conclusion
Boots with chinos will allow you to stand out in a subtle way. The combination is simple to execute, as long as you nail the basics of fit and sticking with styles that match your personality. Once you perfect these two foundational pieces, you can experiment with all the other pieces in your outfit to come up with a variety of looks that offer versatility and personality for almost any scenario.
