Men’s Boots for Fall/Winter 2016

Doesn’t it seem like you’re constantly buying something to accommodate the seasonal changes? Like, didn’t summer just happen? Didn’t I just buy new summer gear…now it’s winter? Well, if you want to be stylish, you will have to stay up to date. Few people can pull off shoes from ten years ago and gentlemen who do are most likely well in their 40s and up. They learned the value of quality and have most likely invested in well-made shoes. With a well-made pair of shoes or boots, you can keep them a lot longer and they’re a lot easier to repair.

It may be time to donate a few pairs of shoes to make room for new ones. As you know, I am a firm believer in investing in quality over quantity. Sure, you may have a few pairs of inexpensive shoes, I love a good deal and have some inexpensive shoes that seem to be indestructible. I will say, the investment pairs are still in great condition and current with the changing times. When it comes to an investment piece or shoe, look for a style and fabrication (material used) that will work throughout the year, not just for one season. Designers that design shoes built to last decades aim to do this. They want the shoe or boot to be just as good a few years from now as they were the first time you opened the box and slipped them on.

Here are my picks for boots this year. I hope you have a good Chelsea boot and if not it’s time to get a pair. A few of these selections may be a tad pricey, but don’t forget it’s an investment and Black Friday and sales are just around the corner. Men’s fashion goes on sale very quickly so you can shop when the prices go down a bit. I have to say I am a bit jealous, men’s clothing sales are amazing. It might be because a lot of men shop when there’s a deal or sale. Smart thinking!

Oh, by the way, I picked boots that can be worn with a suit or a pair of jeans.



Rubber sole, I think that’s pretty much the ultimate detail for a boot that must transition from fall to winter. It’s heavy duty but not clunky. It still maintains a stylish, yet sleek profile. This boot is for the gents who prefer style, function and versatility. I have put Grenson on the list before, so I knew I had to include this brand again.  Did you know that Grenson is the first brand to use the GoodYear welt construction technique? This is a technique that the most reputable brands use. This method  produces a durable waterproof shoe that can be repeatedly resoled. As I mentioned above, well-made shoes can be refurbished many times over. Grenson has a great selection of boots and shoes so if this is your forever go to brand, good choice!



Grenson Black Dawson Boots
Grenson Black Dawson Boots – $425.00





Just like Grenson, Alden uses the renowned GoodYear welt. Another good shoe brand that wants your shoes to last a lifetime. Since Alden wants your shoes to remain in top form, Alden welcomes you to send shoes back for resoling anytime. This is a great example of quality and money well spent. I chose a plain toe leather chukka boot (aka desert boot) that works great with a suit but still has a bit of edge. This style is great with jeans as well. I like chukka boots but sometimes a suede finish can look too casual. This is the best of both worlds. I love the simple lace details as well.


Alden Plain Toe Chukka Brown
Alden’s Plain Toe Chukka Brown – $959.95





RM Williams is an Australian brand that has been making great shoes for over 80 years! As I mentioned above a Chelsea boot is a must have. It’s a contemporary and sleek style of boot that always looks good. If this is the one pair you invest in this year, get a good pair. RM Williams assures you that these boots will last a lifetime and look even better with age.


RM Williams Leather Chelsea
RM Williams Leather Chelsea – $590.66





John Lobb has been making bespoke boots and shoes for over 150 years. Not only can you purchase shoes or boots in store or online, you can also get a custom pair made as well. This is an ankle version of the monk-strap shoe with a topstitched cap toe. A welt stitched double stacked leather heel adds durability, perfect for the winter. Although the monk-strap adds a nice look to shoes, it’s not a style that some of you would want to wear every day. John Lobb created a boot that takes this style up a notch, it’s polished and cool at the same time. It gives you the best of both worlds without compromising on quality or style.



John Lobb Men's William II Double Monk Strap Shoes Dark Brown
John Lobb Men’s William II Double Monk Strap Shoes Dark Brown – $2490.00





To make this list complete I knew I had to have a classic wingtip. A lot of gents like this shoe style. It’s probably one of the easiest styles to dress up or dress down. They work well with a suit or pair of distressed jeans. It’s also something familiar for those who don’t want to go too far off the norm. A classic leather wingtip boot and a Chelsea boot, for those who are looking for long-term wear boots, should make the top of your shoe investment list.

Thom Browne Classic Leather Wingtips
Thom Browne Classic Leather Wingtips – $2084.53



I decide to keep it simple, that’s why I showcased only five pairs for you to get inspiration from! I kept it classic yet cool at the same time to fit your diverse lifestyle. I didn’t select a suede boot but you can go for suede in any of the above styles if you prefer. If you live somewhere with the same weather conditions as Canada, you will notice in most cases that suede doesn’t always make it through the winter. Since many of you will want to spend more now so you can spend less next year (nothing) it’s a good idea to avoid the above styles in a material that doesn’t age well. If you prefer suede, get a pair that’s well-made and don’t forget to use shoe protector for all of your boots and shoes. A lot of brands offer affordable suede desert boots (chukka boots), an extra boot purchase that you wear while the weather is agreeable in addition to the above stylish every day durable boots.


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Author Description

Hanifa Sekandi

Founder & Editor-in-Chief Follow Me on Instagram @thethingsiwishiknew

2 Responses to “Men’s Boots for Fall/Winter 2016”

  1. November 17, 2016

    Ozzie Marrero

    $2500.00 for a pair of boots$ Really? How about an article showcasing AFFORDABLE, quality boots?

    • Hanifa Sekandi

      November 18, 2016

      Hanifa Sekandi

      Hey Ozzie,

      Thanks for the message. As I mentioned, you can use these style as a guide. There are many designers that make affordable versions of the same boots featured. The emphasis here is quality and material used. In addition to how they are made. I will post another post soon on similar styles that are a cheaper price.

      The shoes featured are for those who want shoes that last a long time and can be refurbished. This may not be what you are looking for.

      Thanks for stopping by!