Men’s Fall & Winter Leather Boots | How To Wear Men’s Boots – Dress, Casual, Work, Chukka, Lace-Up

Men’s Fall & Winter Leather Boots | How To Wear Men’s Boots – Dress, Casual, Work, Chukka, Lace-Up

(modern techno music) – Hi, I’m Ashley Weston. I’m a celebrity men’s wear stylist. This video is part of my men’s fall and winter essential series. To see the other articles
and videos in this series, check out the link in
the video description. So today, I wanna talk to you about boots. There are three types of boots that I love during the fall and winter season, a nice dress boot, casual
boot and Chukka boot. Now, the reason why I love boots during this part of the year is because not only does
it look great with jeans, wool trousers and a nice fall/winter suit, but it also keeps your feet nice and warm and protected from the elements while still looking classy and refined. Now, if you live in an area where you get a bit of rain and snow then you should probably
get a specialty boot for those crazier days, but that’s outside of
the scope of this video. So let’s quickly go over the differences between a dress boot and casual boot. So dress boots are formal so they go well with
suits and wool trousers. They also have a sleeker profile and the soles are usually made out of either leather or rubber. Also, the leather itself
is a shinier calf leather as opposed to a thicker cowhide. Now, just think of a dress
boot like a dress shoe but with a shaft on it. So for casual boots, they’re
usually a little less formal and sophisticated which is why
they work so well with jeans, but they also can still be
worn with wool trousers, just not suits. There’s a little bit
more room in the toe box and the leather is usually
made out of a thicker cowhide, although not always. These boots here are actually
made out of a calf’s skin. So the quickest way to
tell between a casual boot and a dress boot is by the soles. So if it has a lugged
sole like I have here then it’s 100% a casual boot. Let’s go over the points
that you should look for in a good boot. So first off, you wanna make sure your boot has a nice, slim profile and what I mean by that is
the height of the toe area. You want it to be nice and slim. A Timberland is the exact opposite of what you’re looking for. Usually Timberlands have
a really high toe area. It’s just super chunky and
that’s not what you want. So make sure you have a
nice, slim, sleek profile with a slim sole. When I say a slim sole,
usually with casual boots, you’re gonna have a little
bit thicker of a sole because usually it has a lugged bottom. That’s perfectly fine. You just wanna make sure it’s not like double this thickness. That’s when it’s just too chunky. Next, your boot should
be either a plain toe like I’ve got here or a capped toe like this boot. And then it can also
have some broking as well which is this decorative
detail that you see here. The next point you wanna
look for in a boot is that it has a rubber bottom. Usually it’s gonna be lugged or Dainite. This one’s Dainite here. Now, you want the rubber bottom because you need that added traction. Otherwise, if you have leather soles, you will slip and slide like crazy in any kind of wet weather. So next thing you wanna look for in a boot is a nice chocolatey brown
and/or black like I’ve got here. I would definitely
recommend going with a nice brown color first because
it goes really great with all of your fall colors and you can wear them with
your formal and casual outfits a lot easier than a black boot. Once you’ve got brown,
then get a black boot. I would just be careful with getting more specific colors like an oxblood because it’s a lot more difficult to wear. It just doesn’t compliment as
many colors in your wardrobe. Only get that color after
you’ve gotten the brown and black boots. And lastly, your boots should not be suede like I’ve got here, unless you live in Southern California where it only rains maybe
three or four times a year, but if you live in an area
where it does rain and snow, do not get suede, instead
get a nice leather boot because I don’t care
how much you Scotchgard the crap out of your suede, it’s still gonna get completely messed up. Save suede for the spring. So in regard to wearing boots with a suit, you certainly can do so, but just make sure it’s a dress boot. And if you are gonna
wear boots with a suit, there’s two things you gotta be aware of. First, you wanna make sure
your suit is made out of a heavier wool material because
your boot are a visually heavy item so you need a heavier
suit to help complement it. Boots look very odd when it’s paired with a lighter weight suit. The second point you wanna be aware of is when you are wearing
your boots with a suit, you have to make sure that the suit pants are hemmed with no brake. So no brake means it’s
gonna hit about here. If you wear your suit pants that you got tailored for dress shoes, it’s actually gonna
create a lot of bunching on the boot itself so it’s
gonna look really sloppy. Unfortunately, what
that means is your suit can only now be worn with your boot, unless you have your
tailor lengthen the hem when the seasons change and when you wanna wear that suit pant now with a pair of dress shoes. Okay, so now let’s get into my
favorite boots you should own and how to wear them. But just a quick note, if you don’t know how to
properly tie your boot then check out my video
link in the description. So first off, I’ve got this Allen Edmonds First Avenue dress boot. I really love this boot because again, it has the nice slim profile. Like all of their dress shoes, the leather is such high
quality and so great. And it also has a nice
rubber sole as well. So I’d style these dress
boots in a black suede bomber jacket with a charcoal turtleneck and throw on some dark washed jeans, but check out the
website for more details. The next boot that I really like is this casual boot by Purdey. I know you’ve seen this in
quite a few of my videos, but I really love the slim profile and this chocolatey brown finish. I pair these casual boots
with a green utility jacket and an Oxford button down. I threw on some dark washed jeans. The next boot that I really
like is this Chukka boot by Johnston & Murphy. This is a very well-designed
boot at a great price point. Johnston & Murphy and Aldo are
actually my two go-to brands when I’m a little bit
more budget conscious. They just make great shoes
at a great price point. So I style these black
Chukkas in a trucker jacket, Oxford button down and
some some wool trousers. So those are some of my favorite
boots that you should own. There’s a couple of other ones
that I really love as well, some suede Chukka options that
I’ve included in my article so definitely check that out via the link in the video description. This video is part of my men’s fall and winter essential series. Check out my website
for an in-depth article that includes all the outfit
details and product links. Subscribe to my channel
for more videos like this and if you like this video,
remember give it a thumbs up. All right, thanks so much for watching. I’ll see you in the next one.

100 Replies to “Men’s Fall & Winter Leather Boots | How To Wear Men’s Boots – Dress, Casual, Work, Chukka, Lace-Up”

  1. I'm liking these new videos. Especially the exceptions like skin tone and locations like southern California. You really should talk about quality more though. A boot video with no mention of a Goodyear welt, isn't a quality video. Pun intended!

  2. I like this setup, it makes it look more classy. But I think some extra lighting would be nice, especially since the shoes are quite dark.

  3. Hi Ashley, great video! I like the new style. I already own a dress boot and a  chukka boot. I would like to invest in a more casual boot and I am torn between the following boots from C&J: or . Which one do you prefer?

  4. Yo, Ash. Thoughts on Balmorals boots?

    I just picked up these though mine are more of a very dark brown than a chocolately colour.


  5. Ashley what if you have a pair of Fry Campus Boots 14L Orange in Color? Also I have a Pair of Cowboy and Block toe Boots with the Buckles in the toward the ankles?

  6. I personally like the suede chukka boots myself especially in brown since they don't seem so formal and flashy and much more laid back and casual especially with jeans.They make those in microfiber that have the look of suede but without the hassle of real suede and even if they get wet or dirty they are very easy to clean.I have a pair of microfiber faux suede chukas that I have worn through rain and snow and after cleaning they still look good 🙂

  7. Any specifics on dress boots vs Balmoral/closed laced boots? Love your videos by the way! They're really welcoming and accommodating to newer or less experienced viewers

  8. i dont really know anything about fashion but now this video is making me think a little more about how i dress haha thanks

  9. Hi, can you make a detailed video on the "military hem" ?

    What should I ask to my tailor? How much shorter should the back be from the front?

    thanks , cheers

  10. hey Ashley, winter commuting in Montreal is too harsh on leather boots. It's hard to stay stylish when you need to walk in snow/slush at -10° and then die of heat in the subway….the struggle is real. Any tips for all of us up north?

  11. A great pair of Tan Chelsea Boots is always my favourite…they always look awesome !! U should have included it 😉

  12. Just found your channel and website recently, it's very impressive. I've been binging on your videos for the past 3 days!

    What about the Chelsea boot, many people think this is also a wardrobe staple?

  13. I agree with kongmw, the previous set up added interest to the shot and subject to the items used also portrayed style. no doubt you'll find a solution, but please don't drop the outakes and general feel of fun as it creates a fab personal touch!

  14. Pretty good video Ashley, I like the way that you explain. Well done. By the way: Do you have a video talking about T-shirts? I´ve been having a few problems trying to find the correct one. Thanks!

  15. Hi Ashley, here one follower from Spain! I've seen all your essential series and I have to say that I love your advices, I've started to following them and I see much better myself in front the mirror so thanks a lot for that, you're really good! Finally I wonder if you can answer me a doubt: I live in a zone that only rains 15 or 20 days per year and I want to buy a pair of chukka boots, should I buy a leather or a suede pair? And which colour? I've to add that my outfits are oftenly informal and really casual. Thanks 😉

  16. the few videos that I have seen I have liked, its always interesting to get the women's perspective on men's fashion…

  17. Another great review by Ashley, though as much as I like Allen Edmonds I ordered a great quality boot from Thursday Boot Co. called Captain Brown for about half the price that fits great and has Dainite style rubber soles.

  18. What type of jeans do you recommend? I like mine tapered at the bottom but I'm having a hard time finding a really nice pair of jeans, any suggestions?

  19. Great video. Would you be interested in doing a tutorial on how to look good wearing wedge sole boots? I recently purchased a pair of Grenson Fred with black wedge soles but found it challenging to wear them without looking bulky. There seems to be very few examples on the internet. Thanks!

  20. I loved this video and your advices, very instructive as always.

    However i disagree about your advices for suede boot. In Paris it doesn't rain a lot, but sometimes its rain.

    I love suede shoes. Actually i prefere suede over leather boot, because suede is so easy to care of.
    But i think for suede leather shoes, its better to wear higher boot like chelsea boot, in rainy conditions.
    I just use waterproof product every 3 weeks. I use brush for suede leather when needed.

  21. Hey Ashley. Is there a significant difference between brown and cognac? I can't really tell the difference. I'm looking at the recommendation you provided for casual boots, specifically the aldo acerrassi. I love the look but can't decide on the color. It would be my first pair of boots btw. Thanks.

  22. Ashley, I think you mentioned an interesting point regarding Timberland boots – when I wear boots or shoes with small toe box my toe tears the dress socks, even a fresh new pair. Would be interesting to hear your opinion about how to rock Timberland boots (without looking like a hipster lumberjack), if in your mind it is possible.

  23. Should I invest in an traditional black Oxford captoe dress shoe like the ones you use with your models in addition to investing in let's say a dress boot like the First Avenue Allen Edmonds. To be more clear can I use the dress boot like I would the black low cut oxford dress shoe and avoid spending money on two shoes?

  24. Can I wear brown boots with an all black outfit. I ask this because at the moment I can only afford one pair

  25. Ashley what do you think of the Allen Edmonds Normandy boots? I got a pair of Aldo's Acerrassi but kind of feel that the quality is so so. The Purdey's look nice but will certainly break the bank. Thanks

  26. Hi Ashley, what about someone about 5'8"? Will a casual boot be fine or will a chukka boot look more in proprtion?

  27. Boots with suits are a tread lightly kinda thing. Depends on the casual suit and the boot. A formal charcoal suit wouldn't look good with any sort of boot outside of a non-decorated black chukka whereas a dark brown chukka looks phenomenal with a navy suit. Lace up boots I'd be hesitant to wear with anything other than jeans or chinos or odd trousers with the right top

  28. Hey Ash! How do you feel about tall HUNTER rain boots in the fall/winter time in rainy regions. If you like them. Which model and color do you recommend? How would you style them outfit wise?

  29. Ashley weston is only stylist which tells us about the first shoe first jacket we should buy i live ashley weston you have made me a lil more stylish now i have more confidence evrryone now ask me about how m i so stylish all thanks to you 😘

  30. @ 1.11 I like how Ashley moves her hand moves up and down that big black boot as she talks about shaft and thickness. Very good video.

  31. Ash is right about winter. Can't do any of these in rough 7 months of New England winter. Slush, ice, snow, mud, salt, sub-freezing temps. I go with handsome mid range leather hi tec hiking boots @$50-70 with grippy soft rubber soles to keep me upright when everybody else is falling on their ass. They have a fairly low – mid profile, keep my feet warm and snug, give great support, and give my height an extra inch and look great with jeans and sweater, and most mens casual winter styling. And if everything is pure ice I can snap on a pair of yaktraks and keep moving. I like to get outdoors in winter and enjoy the season, and good grippy footwear is key.

  32. I really enjoyed your video. I’m currently on the verge of investing in a new pair of boots, possibly two pair. You addressed all of my uncertainties and more, making me a more confident shopper. Thank you so much for this.

  33. Ashley, do you ever like a cowboy boot for casual wear? I am not a fan of Chelsea boots. All of the other boots in your video are awesome!

  34. Suede is actually more durable than you give it credit. Cordovan is also more versatile than brown: Anything you can pair black or brown with, cordovan will go with it too. Except a black suit.

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