When boot season arrives, you can get caught off-guard. Once you pack up the flip-flops and shorts, you may be left wondering what to wear.
There are a lot of different ways for guys to style their boots, and I’m going to share with you some of the most important considerations to make when putting together a boot-centered outfit.
5 Most Important Factors in Styling Your Boots Well
Styling your boots is such a wide topic, I’m going to break it down into five major sections:
- What style of boots are you wearing?
- How do your pants fit?
- Matching colors
- What goes on top?
- Casual, business casual, or formal?
I’ll be sharing how I personally like to style my boots, plus I’ll also share how some other guys rock their boots in ways that I don’t think I could pull off.
Ultimately, there’s no single right way to style your boots.
But my hope is that by the end of this article, you’ll have found how you want to style your boots.
Plus, I’ll share some of my favorite brands to shop with if you’re looking to take a step forward in your fashion game. I think upgrading your wardrobe is one of the easiest ways to make a great first impression.
1. What Style of Boots are You Wearing?
If you’re just getting started in the world of high-quality boots, you may want to check out my video on the five best types of boots you can start your collection with:
You can also check out what I consider to be the best boots right now.
How to Style Chelsea Boots (and Other Narrow Boots)
Because Chelsea boots are more narrow and casual, you can rock any style of pants you want, but the key is to keep the pants slim and tapered.
I like slim fit jeans with taper below the knee, but if you’re in your 20s, you can still rock skinny jeans, so that’s a good option, too.
Avoid straight cut or boot cut jeans with Chelsea boots. Because Chelseas are slim and relatively narrow boots, they look best when your outfit is more streamlined. Too much fabric around the bottom of your pants, and your boots will get swallowed.
Check out my full video with 9 examples of great Chelsea boot outfits below:
Most slim fit jeans have moderate taper below the knee, and skinny jeans typically have the most taper below the knee. I personally like more taper below the knee because I have larger legs. The extra taper helps me look taller and less wide. But if I push the taper too far, I just look top-heavy. It’s a balancing act.
Don’t just box yourself in with jeans, though. The beauty of Chelsea boots is that you can wear just about any style of pants.
I also love wearing chinos with my Chelseas. However, make sure your chinos have decent taper below the knee and you’ll be set.
If you want to know what my favorite Chelsea boots are right now, you can check out this video:
How to Style More Rugged Boots
I think narrow boots like Chelseas are good for certain occasions, but I find myself reaching for chunkier, more rugged boots these days like the Red Wing Iron Ranger.
I pair these types of boots with slim-straight or straight cut jeans because the leg opening is a little wider.
That allows the boot to fit neatly under the pants, and you can always cuff your jeans if you’d like a little more of a tapered look.
I’ll discuss more about the specific types of pants you should get with heftier boots, plus what to wear on top a little later. But I mainly add this here so you know that the weight and size of your boots makes a significant impact on your overall outfit choices.
2. How Do Your Pants Fit?
Once you know what sort of style you’re aiming for (either a slim streamlined look with Chelsea boots, or more of a rugged workwear style with a service boot), the next most important thing to get right is the fit of your pants.
The 6 Pant-Leg Styles You Need to Know About
If you’re anything like I was and aren’t sure what all the differences between slim, slim-straight, taper, athletic, etc. mean, I don’t blame you.
Every brand has their own naming conventions, which makes it hard to know what you’re actually getting. Ultimately, there are really only six types of pant-cuts that you need to understand to make sure you get fit that works for you and your boots.
Skinny jeans and chinos are narrow through the thigh and taper strong below the knee.
This is definitely a younger style and I never recommend it to guys over 30 years old, because it rarely looks good on us older gents.
Skinny jeans look the best when paired with “sock-like” Chelsea boots that are really low profile—the style is more of that rock-and-roll vibe.
Younger guys can pull it off, and I can only speak for myself, but I got a bit softer when I hit 30 and that same look just doesn’t have the same edge it did when I was 24.
A much more mature alternative to skinny jeans is the slim-tapered jean. I’m a big dude at 6’1” and 200 lbs, so I usually don’t fit well into slim-tapered jeans, but it’s possible.
The Kato brand Scissors jeans are made with the brands own 10.5oz Air Raw selvedge denim, which is a really unique fabric. Plus, because it’s not just 100% cotton, it has some 4-way stretch to it, which makes it really comfortable.
Slim jeans have a bit more room in the seat and thigh compared to skinny jeans, but still have that sleek profile all the way through the leg.
This style of pant looks great with slimmer, more narrow boots. A great example is pretty much the entire Thursday Boot Company collection.
Because Thursday boots have a streamlined, narrow toe box, they work really well with a tapered jean or chino. Bulkier boots, like the Red Wing Iron Ranger, look a bit off when worn with slim tapered jeans (though slim-straight could be a good option depending on your body type).
Slim-straight jeans are just as narrow in the thigh as slim-taper jeans, but the leg opening is a bit wider.
So this style works well if you want to wear a bulkier boot, but you don’t have large thighs.
For my body type (larger thighs and hips), I don’t like how slim-straight fits. They’re basically skin-tight around the leg and then at the knee they have the appearance of flaring out.
Even though they don’t flare out, it just looks like I’m wearing bell-bottoms. That’s why I stick with straight cut jeans.
But if you’re not hitting the squat-rack, generally slim fit jeans are a better choice because they look more crisp and put-together.
Straight cut is my personal favorite style for pants. They have plenty of room in the seat and thigh and they’re straight all the way down to the leg opening.
I’ve started wearing a lot of boots from Red Wing, Nicks, Whites, Wesco, Truman, and Grant Stone, and these boots are all a little more on the bulky side, at least when you compare them to a brand like Thursday.
When the legendary White Oak Mills closed down their denim mill, Raleigh Denim Workshop went searching for the best alternative. They found something strikingly similar---now their raw selvedge jeans from the Nihon Menpu mill in Japan are my favorite jeans to pair with boots.
They age beautifully and the break in is surprisingly easy for raw denim.
Pairing a bulkier, high quality boot with a straight cut pair of pants is a more mature look that I think is more fitting for guys at 30 and beyond. Plus, usually 20 year olds don’t have enough money to justify buying a $300 or $400 boot, so the slimmer, more dressy and fashion-forward boots are a better choice financially.
For me, straight cut trousers still fit pretty snug at the seat and thigh, but they don’t look tight like a slim fit would.
There’s no taper below the knee, so they land on your boots the same way a slim-straight jean would.
5. Boot Cut
Boot cut jeans flare out a bit below the knee. I don’t personally wear any boot cut jeans, but they’re the go-to choice for cowboy boots.
However, I actually like wearing my straight cut jeans with cowboy boots. That’s in part because of my personal style. I’m more into the heritage fashion style rather than western style with the big belt buckle and can of chew in the back pocket.
Relaxed jeans are another fit I avoid. For huskier gents, relaxed jeans may be your best bet, but I would suggest at least going and trying on a pair of straight cut jeans.
Or if you can find a brand with an “athletic” fit, that’ll give more room in the seat and thighs without too much bagginess at the bottom.
That’s my big issue with relaxed fit jeans—they seem “swampy” at the bottom and they make you look heavier and shorter.
If you’d like to see my favorite jeans to pair with boots, check out my video below:
3. Matching Colors
As a general rule of thumb, if you’re wearing black boots, try to wear all greyscale. So that means white, grey, or black.
If you have brown boots, then you can expand into a lot more color—I like brown with olive and khaki. I also like brown with navy and white.
I prefer brown boots just because you have so many more options to pair with. But that doesn’t mean you should skip black boots altogether.
Best Styles for Black Boots
Black boots match best with black jeans. If you want to go all the way, throw on a black t-shirt and a black leather jacket.
You can also try other neutral colors like charcoal or navy blue. Just make sure if you go with a non-monochrome color that you tie the black back in like you see here with the black t-shirt.
Best Styles for Brown Boots
When you’re styling brown boots, you’re free to mix and match about any colors you want.
As I mentioned earlier, I like olive green, tan, brown, white, and blues. But even if you gravitate more toward warmer colors like orange, red, and yellow, a brown pair of boots will look better than a pair of black boots.
Because brown boots are generally less formal, you can also cuff the hem of your jeans to get a little variation of color and draw attention to your boots. Many readers here are divided here on whether to cuff their jeans or not, but I’m totally for it.
I think if you’ve got a great pair of boots, anything that brings them more attention is a good thing.
Best Color Brown for your First Pair of Boots
Ok, so maybe you’ve decided to get a brown pair of boots over a black pair. Good choice (it’s what I would do).
But now you have a different issue: there are so many variations on the color brown. Which should you get?
If I were getting my first pair of boots, I would choose something basic and universal like what you see in the image above. That’s brown Horween Chromexcel leather, which has a rich milk chocolate color.
It’s not super dark like the waxed flesh leather, it’s not too light and orange, and there aren’t the same red-tones you see in the oxblood color.
4. What to Wear on Top
A solid t-shirt to match with your pants is all you really need, but if you haven’t already, I highly recommend getting at least one overshirt you absolutely love.
And don’t be afraid to spend a little on an amazing overshirt because it’ll last you forever and you’ll wear it often.
I have about three overshirts that I rely on throughout the fall, winter, and spring. Yes, they were a bit of a stretch on the budget, but I get so much use out of them that they’re worth it. And they define my style.
I also like to have a few buttoned shirts for warmer days and layering. A light wash denim shirt and an oxford will do the trick.
Just like I feel that spending a bit extra on a great overshirt is a wise choice, the same holds true for jackets.
You really only need one great jacket to get you through the winter, so I recommend going hog and getting the best you can afford.
I like something with texture, like the quilted bomber above. Get something neutral, like an olive, indigo, or brown.
In the early fall and late spring, you probably won’t need a heavy jacket. I like a thinner waxed canvas jacket when the temperature isn’t too low.
And when it does get cold, you can always use the thinner jacket as a middle layer, so you can afford to be a bit more adventurous with your color selection. The jacket above is a mustard yellow, which isn’t something I’d normally wear, but it looks awesome with a brown pair of boots.
The Flint and Tinder Waxed Trucker Jacket is a screamin' deal. I got mine with the flannel lining and it's heavy enough to serve as my main coat through the North Carolina winter. It also just looks and feels so cool.
5. Formality Level (Casual, Business Casual, or Formal?)
Your boots should match the formality level you’re going for. It doesn’t make sense to wear combat boots to the office if you’re a Wall Street banker (unless that’s the “in” thing now).
If you’re wearing your boots to the office, I’d stick with something more formal like a leather sole dress boot.
Even with business casual looks, the more formal and dressy your boots, the better.
I work from home, so I basically only have casual boots (though I wear dress boots for weddings, etc.).
You’re probably already familiar with the range of casual boots, so I won’t go on here, but if you’d like, you can look at all the different types of boots here.
How to Wear Boots in Summer
Not a lot of guys wear boots in summer. But that’s a huge mistake in my opinion.
Sure, you’re not going to layer a jacket and wear your huge chunky work boots on a hot summer day, but summer is a good time to bust out the lightweight boots that don’t get as much play in the colder months.
If you get a great-fitting t-shirt or a polo, basically all your style problems in summer are fixed.
Don’t wear your boots with shorts. Just don’t.
My legs don’t get hot, so I don’t mind wearing pants pretty much all summer. If that’s not you, then maybe stick with sneakers and shorts. But if you’re going out in the evening, that’s the time to bust out your boots and strut your stuff.
It Ain’t Easy if You Want to Look Good
So many men don’t pay much attention to their personal appearance.
That’s a huge mistake.
Dressing well is the easiest way to gain status. I’m not going to lie—at some level, status is what we’re all after.
So if you’re going to do it, really do it.
This doesn’t mean you need to wear a suit and slick boots all the time—but piecing together a unique style that looks great and fits well is an easy way to boost your confidence, and to boost the way others perceive you.
To find your own style, browse YouTube and Instagram and find other guys who have styles you can relate to. Pick up one great piece at a time, and within a year, you can have a few amazing outfits you love to wear.
Are boots attractive on men?
Women love seeing a man in boots. They’re the most masculine type of footwear since they’re originally designed for tough work. So yes, when you style your boots well, they’re very attractive.
Why do girls look at guys shoes?
Footwear is an indication of status. If you can afford a nice pair of boots, it means you can afford other nice things. Plus a great pair of shoes means you care about your appearance and can take care of yourself, which likely means you have the ability to take care of others, too.
What does wearing boots say about you?
Wearing a great pair of boots says that you’re willing to invest in valuable things. It says you’re willing to take control of situations, and you’re not afraid to make a statement.