Fall and Winter Boots For Men

There’s 3 types of Fall and Winter Boots for men that I love for this time of year – Dress, casual and chukka boots.

The reason I love boots for Fall/Winter is that they go so well with jeans, wool trousers and fall/winter suits. They also do a great job of keeping your feet warm and protected from the elements – while looking classy and more refined than a pair of hiking boots or something that’s just a straight utility item.

Now, if you live in an area with a good amount of snow or rain, then you should probably have specialty boots for the crazy days, too, but those are outside the scope of this article. 

The difference between dress and casual boots

Dress boots are more formal and can be worn with a suit or wool trousers. They have a sleeker profile, usually leather or dainite soles, and are made out of shinier calf skin, as opposed to cow hide. Dress boots are like dress shoes with a shaft, basically.

Casual boots usually have more room in the toe box, the leather is usually a thicker cowhide that is more matte, and the soles usually have lugs on them. They look a little less dressy and sophisticated, which is why they look so great with jeans, but you can also still wear them with wool trousers.

My Requirements for a good Fall/Winter Boot

These items apply to all the types of boots – dress, casual and chukka boots:

1. A slim profile and not chunky

Timberlands (right) are the exact opposite of what I’m looking for in a good boot. You want a nice, rounded toe box with a slim profile as well as sole like the image below.

dressvsworkbootashleywestoncropped

2. Plain, Cap Toe or Broguing

I like all 3 of them, but just like with my dress shoes, I’ll always prefer a plain or cap-toe, but broguing is also acceptable. Broguing is not really my preference because I think a lot of guys overdo it with the broguing, burnished toes, etc. Too much can easily look gaudy if you’ve got too much going on in your outfit.

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3. Lugged, Dainite or Rubber soles

These will give great grip in any type of weather. A normal dress boot has smooth leather on the bottom and you will slip and slide like crazy in wet weather. If you’re not in a climate with rain/snow, then you can go with straight leather bottoms typically found on most dress boots, but I see no reason to do that when any rubber bottom aside from lugged will look very similar with the extra benefit of additional traction.

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4. Be brown or black leather

Go with nice dark chocolate or walnut brown first, then get black if you don’t have them already. Brown is a great fall/winter color and is easier to wear with casual AND more formal outfits. But be careful about getting a really specific brown color, like oxblood. As I’ve said in my other shoe videos, it’s a great color but doesn’t compliment a lot of outfits, so get that color once you’ve got these basics down.

And please, whatever you do, don’t get those terrible boots that are already worn in. It’s much better for you to wear them in yourself and really personalize their look to your actual lifestyle.

5. NOT be Suede

For Fall and Winter boots, suede is the last material you should consider, unless you live in a dry climate like Southern California where it rains maybe 3 or 4 times a year. Otherwise, they’ll get screwed up very quickly with any amount of rain or snow. I don’t care how much scotch guard you use, nothing can stand up to that much abuse. So save the suede shoes for spring, please.

Can I wear boots with a suit?

Yes, but only when these 2 conditions are met:

  1. You’re wearing a heavier wool or tweed suit.
    For a visually heavy item like boots, you should understand fabric weights and pairing them with similar items. Even straight up dress boots can look odd with lighter weight wool suits. Make sure the wool is atlas 12oz thick. The easiest way to tell what a heavy wool suit feels like in person, is it should be as thick as a wool sweater (not as soft, though!)
  2. Your pants are hemmed to have no break.
    The hem of your pants will look sloppy and bunched at the ankle, otherwise. You can technically cuff the hem of your suit pants to do this, but if they’re super long, it’ll never look quite right. So I usually just get the pants hemmed to no break for this. But that means you can’t wear this suit with anything but boots now…unless you have your tailor let out the hem when the seasons change.

How To Tie Your Boots

Check out my shoe and boot tying video for how to tie your shoelaces properly.

Best Ways To Wear Boots For Men

fallwinteressentialsbootsashleywestonoutfit1

Topman Black Cotton Bomber Jacket 
TopMan Ribbed Turtle Neck Slim Fit
Rolex Oyster Perpetual Submariner Date
Tom Ford Black Snowdon Sunglasses
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Dress Belt

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Parajumpers Anthracite Urban Genesee Jacket
Brooks Brothers Milano Fit Button-Down Collar Dress Shirt
Rolex Oyster Perpetual Submariner Date
Tom Ford Black Snowdon Sunglasses
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Dress Belt

fallwinteressentialsbootsashleywestonoutfit3

Topman Faux Suede Flight Jacket (It’s technically a Peuterey jacket, but it’s only available in Europe)
Brooks Brothers Milano Fit Spread Collar Dress Shirt
IWC Portuguese Automatic Watch
Tom Ford Black Snowdon Sunglasses
H&M Black Melange Wool Suit Pants
Allen Edmonds Decatur Ave Dress Belt

The Best Fall Winter Boots For Men

Casual Boots

Budget Friendly

Aldo Acerrassi

$200 – Aldo Acerrassi

$175 – Aldo Etausen Boot (2 colors)
$175 – Johnston & Murphy Conard Wingtip Boot (3 colors)
$220 – Jack Erwin Carter Wingtip Boot (2 colors)

Designer

$350 – Allen Edmonds Long Branch Wingtip Boots


$318 – FRYE Tyler Lace Up (2 colors)
$395 – Wolverine 1000 Mile Boot 
$725 – Crockett & Jones Coniston Tan Boot
$775 – Crockett & Jones Islay Wingtip Boot

Dress Boots

Budget Friendly

Calvin Klein Darsey Brown Boot

$140 – Calvin Klein Darsey Dark Brown Leather Boots

$60 – Stafford Deacon Wingtip Leather Boots (2 Colors)
$135 – Stacy Adams Madison Boot (2 colors)
$140 – Calvin Klein Darsey Black Leather Boot

Designer

Allen Edmonds First Avenue Black Boot

$995 – Saint Laurent Polished Leather 

$645 – O’Keefe Algy Split-Toe Weatherproof Pebble-Grain Leather Boots
$748 – Brooks Brothers Peal & Co. Leather Wingtip Boots
$1,098 – Brooks Brothers Peal & Co. Cordovan Boots

Chukka Boots

Budget Friendly

Johnston & Murphy Fulton Chukka Black

$140 – Johnston & Murphy Fulton Black Chukka

$130 – Clark’s Desert Boot in Brown Suede
$75 – Aldo Granges Chukka Boot
$175 –Johnston & Murphy Conard Cap Toe Chukka (2 colors)
$198 – Johnston & Murphy Fulton Brown Chukka
$225 – Vince Camuto Branx Two-Eye Chukka (2 colors)

Designer

Allen Edmonds Dundee 2.0 Chocolate

 

$250 – Allen Edmonds Dundee 2.0 Suede Boots (2 colors)
$378 – FRYE Weston Chukka (3 colors)
$1,500 – John Lobb Elmer Chukka

 

That’s it! I hope you liked the article. Please share it via one of the buttons below if you did. 🙂

The Leather Jacket

This post is part of my Men’s Wardrobe Essentials Series. In the series, I give my tried-and-true men’s wardrobe essentials/basics/must haves that every guy, whether a teenager, in their 20’s, 30’s and well past their 50’s should own in order to be a classic, stylish, well-dressed man.

For well over 70 years, leather jackets have represented individuality and a rebellious, manly side throughout American history. Marlon Brando, The Ramones, WWII fighter pilots, and Springsteen all come to mind when I think of leather jackets. A well-made leather jacket is an essential addition to a man’s wardrobe because it will never go out of style, can be dressed up or down, will generally last a lifetime and fit like a second skin.

Watching a man put on a leather jacket is like watching a prize-fighter standing over his opponent after he’s been knocked down. There’s just something about it that harkens back to a classic, badass, bygone era.

What Type Of Leather Jacket Is Right For You?

There are many different types of leather jackets available, some better than others. The biker jacket, what Marlon Brando is known for, is what usually comes to mind when thinking about a leather jacket. As iconic as this jacket is, I don’t recommend it for most guys. The buckle straps, zippered cuffs, and buttoned collar and lapels are a bit much in my opinion. Unless you’re going for the ’50’s greaser or heroin-chic rockstar look, it’s best not to go this route. It often looks much better in print or on the screen than it does in person.

If you like the classic ruggedness of the biker jacket but want a cleaned-up version, the motocross jacket is perfect for you. It has a tabbed collar and less… stuff all over it, which makes it much more versatile. I prefer this style over the biker jacket because the clean design won’t add additional bulk to your frame, so it’s a great choice for all body shapes.

My hands-down favorite of all leather jackets is the bomber style jacket. It has a clean, timeless body style and the elastic, ribbed cuffs, collar, and waist allow the jacket to hug your body nicely, while adding more comfort than the more traditional styles. The leather on these jackets is usually very soft and supple compared to the other styles, so it makes for a perfect everyday type of jacket.

Best Ways To Wear It

The Biker Jacket

If you go the biker jacket route, I highly recommend this AllSaints ‘Conroy’ leather biker jacket ($670). It has all the classic biker details and an awesome slim fit, which is important since you don’t want it to add bulk to your frame. I’ve personally worked with this jacket, and like all of AllSaint’s leathers, the quality and attention to detail is exceptional. The jacket a steal at this price.

Going on a date? Pair with a white button-up shirt, wool trousers, and lace-up leather shoes and watch her salivate the whole night. Switch out the dress shirt with your favorite t-shirt and a pair of dark washed jeans for beers with the guys.

The Motocross Jacket

I’m recommending this Zara jacket for its awesome fit, super clean design, and perfect cognac shade of brown. You may be wondering why it costs less than $100. That’s because this is actually a synthetic leather jacket. But I can assure you, no one will notice. If anything, this jacket is softer, both in feel and in the hit to your bank account than real leather, which is a plus in my book. A brown jacket pairs well with shades of blues, so go with a light blue striped dress shirt, solid navy tie, light brown v-neck sweater, and a pair of dark jeans and brown dress boots to pull this awesome look off. Nix the v-neck sweater if it’s a little warm out or you tend to run warm-blooded.

The Bomber Jacket

If you want something that looks great, is super versatile as well as comfortable, then look no further than the bomber jacket. Whether going out at night or running errands during the day, I’d pair this jacket with a white t-shirt, charcoal or dark brown wool trousers, and lace-up black leather boots. You’ll look put together and not like you’re trying too hard.

Final Thoughts

In my opinion, a well-made leather jacket is an essential addition to a man’s wardrobe because it will never go out of style, can be dressed up or down, will generally last a lifetime and fit like a second skin. When you throw one on, like a well-tailored suit, it’ll make you feel and look better. You’re not just investing in a leather jacket. You’re investing in yourself. Remember that and let’s see those leather jackets!