Chukka, wingtip, hiking.
I wanna talk to you guys about the single item that launched this whole menswear style craze for me.
Leather, wool, nubuck.
The catalyst if you will. The piece of gear that inspired this whole style situation that I find myself in.
Chelsea, combat, Jodhpur.
I’m of course talking about none other than BOOTS!!!
My love for footwear has evolved over the years from being solely(pun intended) a sneakerhead to now having an insatiable appetite for collecting boots. My arsenal currently consists of 5 pairs of boots that I believe offer a very diverse array of options that fit any situation.
I’ve also enlisted the help of my fellow friends to show off some boots that I do not own, but still wanted to share with you guys. We’re gonna spend today going over some basic details of the boot and a few conventional and not so conventional ways to style them.
1. The Chelsea Boot.
The Chelsea is arguably the most trendy boot out there on the fashion scene. The popularity of this boot has skyrocketed over recent years and I honestly do not see it slowing down anytime soon. The particular pair shown below is from my favorite boot company Thursday Boots and it’s actually the first pair of quality boots that I’ve invested in.
The Chelsea is recognizable by two things. It’s one unit upper that offers no kind of lacing system and the elastic side panel around the ankle portion of the boot which allows ease of use when slipping the boot on and off. The Chelsea is great because of its versatility and sleek, no-fuss design.
A suede or nubuck version of the boot would be considered a more casual option, whereas a leather boot can be dressed up more easily. Now, this isn’t to say that nubuck or suede is off limits in an elegant setting, but I personally feel that it can look a bit odd.
Almost every boot is versatile in its own way, but the Chelsea takes this to a new level because of just how far that versatility can be stretched. By default, boots fall into the casual realm of style. Right in the middle of streetwear and business/formal wear. In my example, I tried to test the limits of how to style these boots by carefully sitting on the edge of casual and street, blurring the lines by using the boot as the saving grace.
By now you all should be familiar with bone Adidas hat. We’re going to keep things simple by pairing a slightly oversized Olive crew neck sweater from Cotton On with some distressed black denim that I got from H&M. I pick up the earth tones of the wheat boot with the green earth tones of the sweater and the gold accents in it as well. I couple that with a few gold accessories to really bring things full circle. As I said before, this is a VERY casual way to style the boot, but in my opinion, a style that works nonetheless. I don’t want you guys to feel as if you have to conform to all style rules because you definitely do not.
2. The working boot/ Timberland boot.
There might not be a better piece of clothing that screams Americana quite like the working boot. There might not be a more iconic working boot than the Timberland 6” boot. This boot is timeless in every essence of the word. It’s been stylish for decades and will continue to be stylish for decades to come.
What makes the working boot recognizable is its earth tone colors and rounded almost bulky toe box. Really you can make a case that the entire boot is bulky. Built for withstanding long hours of standing, walking, potential hazards and bearing the support of a lot of weight, the working boot is meant to have a very rugged look to it.
Now, with that being said, the majority of working boots that I’ve seen in my life can be pretty unflattering to the eye. In other words, they’re ugly. Now I know what you’re saying, “Well Meshach they’re working boots they’re not meant to be stylish” and to that, I say “tell that to the folks over at Timberland.”
Timberland has absolutely nailed the combination of function and aesthetics with this boot! It’s bulky but not overbearing to the point that it looks wonky. Heavy but not uncomfortable. And my god are they just a pair of badass boots!
These boots have become synonymous with inner city culture, especially in Miami where I’m from. Between Miami and New York, these boots can be spotted on the feet of its residents all year round. Yes, summer included.
The model shown below is a perfect example of how these boots should be worn. The Timberland boot is a casual boot through and through. Do not, I repeat, do not try to dress these up! Please! It’s a very rugged look that should not be tampered with. A classic pair of jeans, a white tee, and a jacket is the perfect outfit for this boot. Want to switch things up a bit? Maybe a chino pant and a denim jacket or a flannel shirt as a combo. Americana. No matter what, just keep things simple and you’ll be fine.
3. The hiking boot.
An argument can be made that the hiking boot is probably the least popular form of boot that’s worn regularly. You just don’t see them pop up on folks’ feet as much as the others. Nevertheless, I believe that’s an argument that’s slowly fading with each passing year.
The hiking boot finds itself in a strange realm where it might be considered too rugged and too furrowed to be stylish. Kind of like the working boot. Hell, it might have a tougher look altogether than the working boot. The hiking boot has been told to stay in its place and to serve its very niche audience. I personally think that is absolutely ridiculous.
The hiking boot has way more casual options to wear than the working boot and it’s not even close. The hiking boot consists of a tough upper, which normally contain half eyelets near the ankle portion of the front. That may be the key indicator that you are dealing with a hiking boot. They also tend to come with a durable lug sole, meant for traversing various terrain.
A hiking boot is also usually no shorter than ankle height and can even go up to the lower calf region. The pair that I am wearing happens to stop just above the ankle and provide an almost wedge-like rubber sole across the entire foot. This particular boot also happens to come from my favorite boot company Thursday Boots. It’s the second version of their Commando boot. The previous version had more of a standard, casual boot sole with the same durable, thick upper. That’s the beauty of a hiking boot. It normally has a rugged upper but the sole can be swapped out for many different styles while overall still keeping the same strong look.
I went in a bit of a different direction with these hiking boots by wearing them with a pair of skinny olive denim from H&M, a green camo hoodie from Young & Reckless and a black leather racer jacket that I got from Express, over the hoodie. It’s a very dressed down approach, as it should be, and it’s topped off with a black Ralph Lauren beanie.
4. The military boot.
The military boot is what started it all for me and my boot adoration……nay, obsession. The Chelsea boot may be the hot trend of the past 2-3 years, but the military boot has been the iconic fashion staple for generations. It’s the easiest model to design and almost impossible to mess up. Every brand that has ever wandered into boot territory has some kind of military model in its archives. With a lot of companies, the military model is probably the first boot that they’ll design as it’s the safest bet.
The military boot has a very slim profile that runs throughout the boot. An anti-work boot if you will. Because of this design, I wholeheartedly believe that the military boot must be worn with pants no wider than a slim fit. Anything else will just swallow the boot and ruin the entire look.
My personal belief is that military boots look their best when in the casual section of dressing. The boot most definitely can be dressed up, especially when you bring different materials into the equation such as canvas and wool, but I do believe that they shine their best when kept casual. Pair them with denim, chinos, slacks, a white tee, leather jacket or a turtleneck. The combinations are endless.
The model shown here is rocking a pair of Taft Jack Boots in Oxblood and grey with light washed distressed jeans, a sleek maroon hoodie, and a denim vest to go over it. Not too much going on to distract from the beauty of these crafted boots. If I had to suggest a boot to start your collection with, it would hands down be the military boot. Cap toe or not.
5. The wingtip boot.
Meet the military boot’s elegant cousin who has a taste for cashmere wool and truffle topped Caviar. If you ever got the itch to wear a pair of boots with your suit or tux, this is going to be your safest bet. Meet the wingtip. Since the wingtip shares so many similarities to the military boot, we’re not going to spend too much time on this one.
If you can’t tell by now, the wingtip gets its name from the full brogue on the toe area. A full brogue is the formal name of the extensions that spread out towards the side of the forefoot area like “wings.” This boot was made for elegance, so much so that I don’t even believe that they’re offered in any form of material other than leather.
Now with that being said, the wingtip isn’t meant only for dressed up occasions. I think that the wingtip should go no lower than casual wear and if I had to get really specific I’d say night time casual, like going to a lounge or maybe on a date. This boot screams “I think that I’m more stylish than you are.” This ain’t your first boot option, but it just might be your best. Personally, it’s my favorite style of boot because of its elegant and refined design.
In this example, I pair these wingtip boots from Express with my navy skinny fit chinos from H&M, a super lightweight tan Henley (also from H&M), a denim jacket from the GAP and my beloved wide brim fedora from Urban Outfitters. This is a casual look that’s a little bit elevated in my opinion. It’s an outfit that stands out in all the right ways with a little pop from every level of the body. Notice how the chino drapes perfectly over the ankle of the boot and doesn’t cover up too much of the boot with excess fabric. That’s how pants should fit on a military styled boot. When you’re ready to take your style and boot game to the next level, invest in a quality pair of wingtips.
6. The Chukka boot.
Our last boot of the evening is another classic and iconic model in the Chukka boot. The Chukka is one of the few boots in existence that can work well across the entire style spectrum. They can be worn casually, semi formally, business casual, formally and super casual. The super casual form of the Chukka is also known as the desert boot, but we’ll get into that in a future post where I cover Chukka boots in general.
It’s hard to dispute the Chukka as being the most versatile boot ever created. I mean, it just works. Plain and simple. The design is practically perfect. The lacing system starts at the midfoot of the shoe and since the Chukka is an ankle boot, the laces travel upward only by a little. This makes the Chukka very easy to slip on and off since there’s very minimal lacework. Other than that, there isn’t anything else really going on with the upper. Not a lot of moving parts, no fuss, just a sleek model that works with everything. The more pointed toe box, like what’s shown below, provides a dressed-up option as opposed to a rounder toe which is reserved for a casual option.
Here I want to show how the Chukka boot can be dressed up with a suit. Oh and by the way these Chukkas are from Thursday Boots as well. Moving on; these chocolate leather boots are paired with a blue/grey double breasted suit from Boohooman, a maroon short sleeved button up shirt from Express and my fedora from earlier.
This could have easily been a full on suit with tie and vest, but I wanted to show off a bit of a playful side by unbuttoning 3 buttons on the shirt. Also, notice how the leather in my belt matches with the leather in the boots. It doesn’t have to be a perfect match, but I always feel like the closer it is, the better. Similar to how the military boot is a great option for a first time boot buyer, the Chukka is right up there as far as safe decisions.
It can be said that this was one of the longer, if not the longest post so far, but I just get so fired up about boots. This was by no means meant to be a full-blown detailed guide to boots, but I wanted to give some pointers and thoughts as an intro for a first time boot buyer. I seriously believe and will argue that the boot is the most versatile piece of footwear ever. EVER. That’s how much I love and believe in these things. Anyway, I hope this article helps and be sure to be on the lookout for when we cover more boots in the future.
As per usual, I’ll link to the boots down below so that you guys can easily check out what’s being worn in this post. Make sure to follow me on Instagram for more style content! Click that button down below and it’ll take you directly to my profile!
That’s all for now peeps. Till we put the pieces together again.
Chelsea Boot: https://thursdayboots.com/products/mens-duke-chelsea-honey-suede?collection=mens-boots-chelsea
Timberlands: https://www.timberland.com/shop/mens-6-inch-premium-waterproof-boots-wheat-10061024
Hiking Boot: https://thursdayboots.com/products/mens-commander-hiker-boot-black-matte?collection=mens-boots-rugged
5 thoughts on “Boots!!!”
Awesome post! Keep up the great work! 🙂
Thank you! I will!
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