BEST BOOTS FOR WINTER | 3 ESSENTIAL BOOT STYLES FOR EVERY MAN'S CLOSET
DECEMBER 28, 2019
Three Essential Boot Styles to Complete your Closet
It’s officially winter and our attention is now on cold weather gear. Rightfully so. One of the most important elements that comes along with the season is a good pair of boots. It goes without saying (though, here I am saying it again) that everyone needs at least one solid pair of boots to carry them through winter, unless you’re blessed with sunny days year-round. We’ll deal with you later.
WHAT KIND OF BOOT IS THAT ONE SOLID PAIR?
Photo by Danielle Webster | Electric Lady
Choosing a type of boot that works for you is challenging when there are so many options. I say that even as someone with a hefty collection. And, how do you know when you’ve chosen “the right boots?”
Like everything else, there unfortunately isn’t a single definition for the “right” pair of boots. Right for you might mean a pair that goes with all your outfits, a pair that withstands harsh weather, or even a pair that stands out to you because of style. It becomes more about your needs, interests, and personal style. But, that doesn’t mean the decision gets any easier.
SOME BOOT BLOG DEETS
Rather than give you a general style guide to boots or a “my top picks for you” kind of blog, we’re digging deeper into identifying three styles of boots and why they’ll round out your overall winter style.
Doing a kind of “teach a man [or woman] to fish” thing over here. That way, if you’re stuck on what kind of boots you need, you can reference this guide when you need help picking this winter!
3 ESSENTIAL BOOT STYLES: CLASSIC, RUGGED, BOLD
Walking into a store and trying to select a single pair of boots - particularly if it’s your first pair - can be overwhelming, That’s why I’m breaking it down into three essential styles of boots that belong in everyone’s closet.
Pretty simple when you just say it out loud, right? Compartmentalizing boots into classic, rugged, and bold styles is how I begin to incorporate them into my fall and winter outfits. If you’re covered in these three areas, then you’ve got yourself a well-rounded boot closet.
Classic, Rugged, Bold -Build a Balanced Boot Closet
Photo by Danielle Webster | Electric Lady
We’re going to walk through each of these styles of boots in depth. You’re going to figure out what you’re missing from your closet, how to identify the characteristics of each style of boot, and get some of my tips on styling boots for winter.
A STARTING POINT FOR YOUR BOOT STYLE - NO HARD RULES
As you continue to develop your style, your own essential boot styles might change. And that’s great! There’s no one way to do this and nothing I’m going to share is a hard rule.
But, if you’re looking for somewhere to start, or even just need to organize your extensive collection, starting with these categories builds a good foundation.
Ok, I’m excited! Anyone else? Let’s get into it.
THE CLASSIC BOOT STYLE - BOOT BASICS
If there is one place you’re going to start, whether it’s you need your first pair of boots or a workhorse pair that will pull their weight, a classic style is for you.
You’re going to be able to dress these boots up or down and wear them to the office or out for the night.
WHAT MAKES A CLASSIC PAIR OF BOOTS CLASSIC?
And how many times can I say classic? So many more.. Trust me, just watch.
- Back to boots. -
CLEAN LINES, SILHOUETTE, MINIMAL DISTRACTIONS
Something that sports clean lines, a defined shape/silhouette, ankle height, with minimal eccentric details screams classic pair of boots to me.
That’s not to say that these kinds of boots are by any means boring. In fact, you’re looking at a timeless boot design. A pair of classic boots are going to wear you out before their style wears out.it is, the way you tell your story online can make all the difference.
CLASSIC BOOT STYLING
Photo by Danielle Webster | Electric Lady
Beckett Simonon let me choose these Dowler Boots to highlight this style. While I styled the garments with a modern flare, the Dowler Boots ground the whole look with their timeless design.
You’re seeing those really clean lines and minimal distracting details we just identified create a great foundation.
THE PERFECT PAIR OF NICE BOOTS
The Dowlers also sport a cap toe. That, to me, is a very classic detail when it comes to boots (or really any shoes). It gives the front of your boot some definition, but in a refined way.
QUICK TIP: BOOTS WITH TIMELESS DETAILS WILL WORK IN CASUAL AND FORMAL SITUATIONS
On their own, these boots are a bit dressier, but they can certainly be styled to work in a casual outfit. Sub in solid color chinos or denim and fully tuck in the shirt to bring the whole look back to a more traditional feel in this case. Add dress pants, and you’re ready for the office.
The minimal details we talked about earlier help you take them from formal to casual. That sleek and almost minimal design helps create the foundation for an outfit that you’re looking for.
Photo by Danielle Webster | Electric Lady
MULTI-PURPOSE AND EFFORTLESS BOOTS
They’re a simple, well constructed black boot that will look great with slacks, denim, or even printed chinos. That’s exactly what you’re looking for in your classic styles of boots.
A classic pair of boots, like the Dowlers, are going to be the ones that you can just throw on and head out the door. That makes them some of the best men’s boots for everyday wear.
CLASSIC BOOT COLORS
Your boot color is a big player as well. Black and brown fit this style so well. These will match a lot of your outfits.
If you’re limited to choosing one color and it’s your first pair of boots, I’d recommend going with a brown. The warmth and richness of a cognac or honey color make it easier to pair with a lot of other colors in your wardrobe.
The black inevitably looks a little more formal, which might not be what you want for every occasion. Though, to be honest, you can’t go wrong with either.
TYPES OF CLASSIC BOOTS
The Dowlers aren’t the only shape or type of boot that files nicely under the classic boot category. I’ve linked a few more from Beckett Simonon’s website at the end of this post.
You’ve got classic ankle high boots, chukka (desert style) boots, and Chelsea boots there. Any of those could be your classic, work horse pair.
VARYING THE DETAILS CHANGES THE BOOT STYLE
Whatever it is, the way you tell your story online can make all the difference.
Once you start varying color, stitching details, and materials, you start edging into something more modern and bold. The classic boot style serves as a base for a lot of new boot design in that way.
BOOTS WITH TIME TESTED STYLE DEFINE THE CLASSIC CATEGORY
I personally love a timeless style done in a new way (with color or unique materials), but that isn’t necessarily the true classic style of boot we’re talking about here. We want boots that work every time you put them on.
Take if from Beckett Simonon:
“Great style is timeless. Instead of chasing trends, we take inspiration from classic designs to craft refined and luxurious products. Whether you wear them with suits, jeans or chinos you can be confident these designs will never go out of style.
— https://www.beckettsimonon.com/products/dowler-boots
CLASSIC BOOT WRAP UP
In the end, the key to styling a classic pair of boots is really just swapping them into your current outfits and using them as an anchor for the rest of your garments. That kind of versatility is a cornerstone of the style.
These aren’t your grandpa’s kind of boots…
Actually, they might’ve been, but that’s because their style doesn’t diminish and your grandpa clearly had great taste. They’re elegant, refined, and are going to look great as your go-to pair!
THE RUGGED BOOT STYLE - ROUGH AROUND THE EDGES
Throw on your buffalo check plaid and grab your axe because when I’m talking rugged I mean something rougher around the edges in terms of boot style.
Ok, ok, you can skip the axe (keep the buffalo check for at least a few outfits though).
You know what? Keep the axe... It’s pretty cool too.
- Rugged boots. Right, sorry. -
When I think rugged, I’m also thinking functional. I lump boots that give you an unkempt edge and boots that can weather rainy, slushy, and snowy conditions into one category.
Photo by Danielle Webster | Electric Lady
FUNCTIONAL RUGGED BOOTS
Sidebar - if you don’t have a pair that can keep your feet warm and dry during a snowstorm, then forget what I said first in the classic section above. You NEED some weatherproof ones.
If you’re looking for a pair of waterproof boots, I recommend the Sperry Duck Boots or the L.L.Bean Boots. Those look good and are going to definitely work for you. You need waterproof if you live in a snowy/rainy climate this time of year. Sidebar complete.
Most rugged boots are going to be able to handle some weather and slick ground, but make sure you have something for really bad weather if you need it.
DEFINING RUGGED DETAILS
Photo by Danielle Webster | Electric Lady
The rugged details embody anything that has elements of workwear and work boots. These would be moc toe and stitching, a Vibram sole, full grain leather, and an overall boxier or bulkier construction. It’s that sort of blue collar aesthetic.
QUICK TIP: LOOK FOR WORK BOOT STYLES TO GET THE RUGGED LOOK
This style of these boots is definitely going to lend itself to a more casual outfit. Typically, I’m thinking denim, overshirts/work shirts, beanies, and that buffalo check plaid again! Heck, throw some Carhartt in there if you’re so inclined.
You can also choose to give a rugged finish to a casual outfit that doesn’t have those elements. That can be a more creative way to work these in.
RUGGED BOOT STYLING
That’s usually what I do when I’m styling a rugged pair of boots. Unless I’m out on the construction site all day, then it’s just full work wear. In general, I like taking something more traditional and finishing it with rugged details.
Sutro Footwear let me try these Charlton Vibram Boots in black and I paired them with chinos, a striped polo, a mechanic’s jacket and my grandpa’s old pilot’s jacket.
See? Grandpas do have style.
The polo and chinos on their own are pretty classic, and not necessarily what I would call rugged. The Charlton Vibram Boots break up that traditional feel of the pieces. The boots also inspired me to layer up the rugged jackets to bring the look home with “rougher” looking elements.
INTERRUPT TRADITIONAL STYLING WITH A RUGGED EDGE
Photo by Danielle Webster | Electric Lady
My favorite part about rugged-style boots is that they can interrupt the classic and refined nature of an entire look. It really puts a hard stop on the end of an outfit.
The Charlton Vibram boots do that here. They bring the chunky Vibram sole, bulky shape, and roughly finished materials that are so characteristic of a rugged boot. Plus, that Vibram sole is so comfortable. There’s no trouble wearing it all day.
QUICK TIP: PAIR RUGGED BOOTS WITH DENIM AND A BUTTON DOWN FOR AN EASY LOOK
Styling these with denim won’t ever fail you. In fact, that’s what first comes to mind. Cuff your denim, show off these puppies, and add a shirt or your favorite layers up top for a winning outfit every time. I bet you can picture that pretty easily already!
RUGGED BOOTS GO CASUAL
These boots tend to dress down an outfit. I wouldn’t recommend wearing these to too many formal events. If your style tends to lean more casual, with fewer formal requirements, then styling them for everyday won’t be an issue.
RUGGED BOOT WRAP UP
Rugged boot style comes more from the construction, shape, and materials of the boot. They’re not defined by the color.
Though they’re definitely workwear inspired, they’ve transcended the style borders within casual men’s fashion. You can find a lot of folks wearing them outside of a blue collar workplace.
It’s the rough-around-the-edges style mixed with everyday casual that makes them a fun and creative experience to style.
Rugged Boots - Easy Addition to Casual Style
Photo by Danielle Webster | Electric Lady
LUMBERJACK OCCUPATION OPTIONAL FOR THESE BOOTS
In other words, you don’t actually have to be a lumberjack or carpenter to wear these. But, they are one of my essential styles of boots because they’re an effortless casual choice.
Fashion focused or not, there isn’t a huge leap outside your comfort zone to get into a really solid pair of rugged boots.
THE BOLD BOOT STYLE - PUSH THE BOUNDARIES
Speaking of your comfort zone, it might be time to step out of it with a bold pair of boots. There’s been a recent wave of brands stepping into signature style and pushing their own boundaries. It’s inspired me to do the same with my style.
GO FOR BOLD BOOTS - SHARE YOUR PERSONALITY
Photo by Danielle Webster | Electric Lady
That’s not to say that you should abandon the classic style, but it’s refreshing to see a lot of new and unique designs make their way into the market. It’s giving us an opportunity to share our personality through our style. That’s why I think bold boots are totally worth it.
WHAT MAKES A BOOT BOLD? - MODIFYING TRADITIONAL BOOT ELEMENTS
Such a loaded question.
It’s all about taking foundational, classic boot elements and tweaking them. Change the color, add a print, or even modify the sole. It’s limitless and all about an unexpected twist. The more elements get changed and tweaked, the bolder we go.
Don’t get me wrong, though, I’m still a practical guy. My ideal kind of bold boot doesn’t mean going completely unwearable.
QUICK TIP: MAKE SURE YOU CAN STYLE AN OUTFIT WITH YOUR BOLD BOOTS BEFORE YOU PURCHASE.
Photo by Danielle Webster | Electric Lady
It’s important to look for styles of boots that you’re actually going to wear. And I mean really wear, like not just once to a single event.
We don’t totally have to lose versatility and utility just because we’re pushing the envelope.
BOLD BOOT STYLING
Taft sent me this pair of Jack Boots in Eden. Let me tell you, there’s no shortage of bold boot style here. We’ve got a traditional boot construction and silhouette with a navy color (bold), contrasting toe and heel (bolder), and reflective gold florals (boldest).
We’ve hit maximum bold boot style capacity!
WEARABLE BOLD DETAILS
Taft knows their way around a bold boot. They take those classic styles and really punch up the design elements to make them something you’ve never seen before.
And yet, the classic elements they leave in their boots (timeless construction, soles, quality, etc.) makes them work in more ways than one. It’s that sort of twist on classics that inspired my styling with this whole outfit.
YOUR BOLD BOOT STYLING OPTIONS:
Whatever it is, the way you tell Photo by Danielle Webster | Electric Lady
1. TURN UP THE ENERGY OF YOUR OUTFIT TO MATCH THE STATEMENT YOUR BOOTS ARE MAKING.
2. TONE DOWN EVERYTHING AND LET THE BOOTS PUNCTUATE YOUR WHOLE LOOK.
Either way you’re not doing it wrong.
I danced between 1 and 2 with this outfit. So I guess that’s kind of a third way to do it.
I can’t even follow my own rules! I couldn’t resist letting these boots stand out.
QUICK TIP: PICK COLORS FROM YOUR BOLD BOOTS FOR YOUR OTHER PIECES.
I chose tones from the boots to play into the rest of the outfit to help connect it all.
I took the modern twist on casual styling further with this look by selecting traditional pieces but combining and wearing them in a non-traditional way. It’s the slouchy beanie, half-tucked shirt, cargo pants, and baggy nature of the outfit that does it.
In doing so, these boots now add a refined and visually entertaining touch to a tougher street outfit with traditional elements. story online can make all the difference.
THE SKY’S THE LIMIT
If you’re going bold, you can really go bold everywhere else in your outfit too. I purposefully didn’t provide in depth styling tips for these because your definition of bold is totally up to you. I’d love to see what you do with it on your own!
The best part about doing something bold is that you can really throw the guidelines out the window and do whatever you want.
TONE IT DOWN
If that kind of full force modern styling isn’t for you, then just throw them on with a pair of denim and a shirt. Your bold boots are going to work just like any other regular pair too.
They’ll do the talking for themselves.. And the walking for you. Truly full service here.
CONFIDENCE IS KEY TO BOLD BOOT STYLING
Photo by Danielle Webster | Electric Lady
The hardest part about styling, or even just purchasing a pair of bold boots, is having the confidence to wear them.
If your first thought was “I can’t wear something like that,” I feel you, but you totally can. If your second thought was “what will people say?” then you’re giving too much credit to others’ opinions and not enough to your own.
QUICK TIP: YOUR BOOT STYLE (AND OVERALL STYLE) ARE UP TO YOU!
All you have to do is take the first step - in a really good pair of boots this winter.
If there’s one true piece of advice I can give you it’s to experiment with your style until you find what you like and feel good in without binding yourself to what you might get some judgement.
So try the dang boots!
BOLD BOOT WRAP UP
A bold boot is one of my essential boot styles because everyone could use that wow factor.
When you’ve got something traditional and something rugged in your closet, your next step is getting something that’s guaranteed to turn heads, even - dare I say - break necks!
MORE THAN ONE WAY TO DO BOLD BOOT STYLE RIGHT
That’s right, you get to choose how to do it and what you consider to be bold. There are no defining characteristics or colors, because they can go any direction.
So many elements of a boot come together to make it whole, and varying any of them can make a boot stand out. Just make sure you’re picking up a pair of boots that you’re going to wear!
MASTERING THE 3 ESSENTIAL BOOT STYLES
Classic, Rugged, Bold. These three essential boot styles meet your winter needs. Having a pair that falls into each category will help you balance your winter footwear game.
HIDDEN THEME ALERT:
Basically any of these styles of boots are going to look great with denim and a shirt. That’s the magic of these three essential styles of boots! So while styling them is pretty simple, its your choice on how you bring them into an outfit. Hopefully, you’ve got some ideas now.
ONE LAST THING:
These styles intersect. You can take a classic or rugged style and add it to more modern garments. Or, you can conversely add a pop with a bold boot to a more traditional outfit. Exploring those possibilities with these three foundation boot styles becomes even more fun! In any case, using these three styles covers you for a lot of combos this winter.
Photo by Danielle Webster | Electric Lady
ARE THESE YOUR 3 ESSENTIAL BOOT STYLES?
If you feel like your boot styles are evolving into something different or you already defined your own like I mentioned earlier, please share! I’m always eager to discuss. As you develop and define your style you may find that different boots styles define your collection.
These are the style categories I think about when purchasing and styling boots for the season. None of this is prescriptive or restrictive. This can serve as a good jumping off point for your own boot needs this winter!
LAST BOOT DETAILS
In addition to the links above, I’ve linked a few boots from each brand that fall nicely into the three essential boot styles. Each brand is definitely not limited to the single style, but I’m a fan of these.
CLASSIC BOOTS:
Use code “Thread20” at Becket Simonon for an additional 20% off discount!
RUGGED BOOTS:
BOLD BOOTS:
UNTIL NEXT TIME!
Thank you so much for reading! I’d love to get your feedback so I know what you liked and didn’t like about this blog. Do you agree with these three essential boot styles or do you have anything to add?
Stay tuned for the next Style Breakdown!
Cheers,
David Komisarchik; Threadability (@threadability)
Tagged: Winter, Boots, Boot Season, Men's Boot, Men's Style, Men's Fashion, Menswear Blog