Fall and Winter Boots & Shoes 2017

In this article and video, I wanted to show you some of my favorite boots and shoes for this Fall & Winter. If you missed my big men’s Fall & Winter Essentials series, you should definitely check that out first, since this is more of a supplement to that instead of the other way around.

Suede Boots

Although you can certainly go with leather boots, I am a huge fan of these suede ones by Allen Edmonds. Everything from the superior construction, to the neutral taupe grey color, which I’ll often use in place of black or brown, easily makes this boot a winner in my eyes.

$350 – Allen Edmonds taupe suede boots
$620 – AllSaints bomber jacket
$24 – J.Crew t-shirt
$118 – Banana Republic slim-fit jeans

Alternate Suede Boots

$285 – AllSaints suede boot

Suede Chukka/Desert Boots

Another favorite of mine are these suede chukkas (aka desert boots) which lend a very Autumn feel to any outfit. Again, just like with the boots I mentioned before, you can certainly go with regular leather Chukka boots, as well. But I love these, specifically because they have a slim profile and a comfortable crepe sole which will feel like you’re wearing sneakers. Pair them with jeans or chinos for a put-together casual look.

$295 – Allen Edmonds chukka boots
$230 – Allsaints denim jacket – One of my favorite denim jackets currently available. I love the lighter wash and distressed touches and the slim fit is incredibly flattering, which is really hard to find in denim jackets.
$20 – Topman striped t-shirt
$68 – J.Crew slim-fit stretch chino pant in green and brown (click here for their straight leg chinos) – I’m shocked at how spot on the fits and materials are.
$128 – Brooks Brothers suede belt in brown
$318 – John Varvatos sunglasses
$10 – Perlon Watch Strap

Alternate Chukka Boots

$168 – Banana Republic suede chukkas

Double Monk Strap Dress Shoes

Dress them up with a suit of down with jeans and a blazer. Double monk straps are timeless and will forever be a Fall (and Spring!) favorite of mine.

$120 – Johnston & Murphy double monk straps
$62 – J.Crew merino wool cardigan (currently on sale for 30% off)
$49 – Brooks Brothers navy plaid shirt
$358 – Brooks Brothers green sportcoat
$168 – Diesel slim fit jeans

Alternate Double Monk Straps

$150 – Aldo double monk straps

Grey Sneakers

Outside of white sneakers, grey is a Fall favorite of mine because it’s another neutral color that compliments the darker, more jewel-toned colors you’ll be wearing this season. You can go with suede, leather, or a fabric material, but just make sure to keep the design simple like these ones.

$215 – AllSaints Low Top Sneakers
$80 – J.Crew cardigan bomber (currently on sale for 30% off)
$24 – J.Crew white t-shirt
$118 – Banana Republic slim fit jeans

Alternate Sneakers

$80 – Converse Jack Purcell suede sneakers (or fabric option here) – I also like these suede sneakers as well.

3 Outfits Every Guy Needs

My articles and videos almost always center around a specific piece of clothing or accessory, so I thought it would be fun to switch it up and talk about 3 head-to-toe foundational outfits every guy needs. Once you have these 3 outfits, you can build an entire wardrobe around them. And here’s the beauty of them: from these 3 outfits, you can switch things in and out to add your own personal touch and truly make them your own.

Outfit 1

The first outfit is a casual one, comprised of a black polo shirt, a well-fitting pair of dark wash jeans and some white low top sneakers. This is a solid casual outfit that will always look great and put together on every man, regardless of your age or body type.

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$198 – John Varvatos Collection Hamptons Silk & Cotton Polo Shirt in black or charcoal (Best luxe polo shirt!)
$13 – H&M Polo Shirt Slim Fit in black (**THESE ARE THE BEST POLO SHIRTS!!!!)
$165 – J. Brand Tyler Taper Fit in slate resin (Love that the color, stitching, and hardware are similar color)
$55 – Levi’s 511 Slim Fit Stretch Jeans in dark hollow
$410 – Common Projects Achilles Leather Sneakers in white
$60 – Adidas Originals Stan Smith (colorway: white/white/fairway – Also available @ Footlocker)
$415 – Tom Ford ‘Snowdon’ Sunglasses
IWC Portugieser Automatic Watch

Outfit 2

I like to call this outfit ‘dressy casual’ because it transitions well from day to night. Throw on a leather or cotton black bomber jacket with a black t-shirt, dark wash jeans and black leather chukkas.

If you’re thin to average build, you can also wear a white t-shirt. However, if you’re a broader man that’s not in shape, and you decide to take off your jacket, then a white t-shirt will actually spotlight how big you are (and not in a good way). Also, the reason why you want to go with black chukkas is because black is the dominant color in your jacket. I went with leather chukka boots over suede and lace-up boots because the latter options won’t look appropriate for every season.

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$670 – All Saints Mower Leather Bomber Jacket in black (LOVE how minimal this jacket is – definitely a BIFL!)
$88 – Everlane Cotton Bomber in black
$60 – James Perse Clear Jersey Crew in black
$10 – H&M Crew-neck T-shirt in black
$170 – Diesel Buster 0607A Tapered Jeans (I’ve bought my fiance 3 pairs of these – they’re that good!)
$55 – Levi’s 511 Slim Fit Stretch Jeans in dark hollow
$175 – Johnston & Murphy Conard Cap Toe Chukka in black

Why a bomber over a blazer?

A bomber is a very stylish, modern alternative to a blazer that works in almost all the same occasions and looks great for every man, regardless if you’re a teenager all the way to a retiree. A younger gentlemen in high school or college, for instance, wouldn’t necessarily need a blazer, so that’s why I’m not recommending it over a blazer. If the occasion does call for a sport coat or blazer, in a pinch, you can use the jacket in my next recommendation and dress it up like I did in the picture below.

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Outfit 3

Lastly, my classic go-to formal outfit is a charcoal or navy suit with a white semi-spread collar dress shirt, black or charcoal tie, white pocket square, and oxford dress shoes. If you’re going with a charcoal suit, then pair with a black tie and black dress shoes. For a navy suit, pair with a charcoal tie, and dark brown dress shoes.

I love these two suits because it’s very easy to go formal by adding a tie or dress them down by forgoing a tie or swapping in a t-shirt instead of a collared shirt.

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$1395 – Burberry Modern Fit Wool Part Canvas Suit (charcoal)
$498 – Brooks Brothers Red Fleece Grey Suit
$115 – TopMan Grey Slim Fit Suit (alternative for warm climates: Topman Charcoal Linen Suit)
$280 – Allen Edmonds Carlyle Plain-Toe Oxfords (black or brown)
$120 – Aldo Bandolla Dress Shoe (black)
$19 – The Tie Bar Grenafaux Tie (My, hands down, favorite solid tie – go with black or charcoal)
$10 – The Tie Bar Solid White Cotton Pocket Square

Spring/Summer Suede Jacket Outfit

I came across this image that I thought would be a perfect Spring & Summer men’s suede jacket outfit because it’s a great, casual everyday outfit that you can wear when you’re going out with friends or if you work in a casual work environment. It has the added benefit of being able to be dressed slightly up or down as well as layered depending on the weather.

 

Jacket

A suede jacket is perfect for Spring and Summer and will look great on every guy, regardless of age or body type. But if you’re not into suede, or like other styles, look no further than the Harrington jacket or a wool bomber jacket.

$1,455- A.P.C. Louis W Suede Bomber Jacket
$1,085 – Hackett Mayfair Suede Bomber Jacket
$160 – TopMan Faux Suede Formal Bomber Jacket

Shirts

The plaid shirt underneath the grey sweater can be switched out for your classic white or blue oxfords or other fun colors or patterns like navy and/or green plaid or gingham.

$188 – J. Crew Albiate 1830 Ludlow shirt in red plaid
$139 – Steve Alan Masters Shirt
$92 – Brooks Brothers Non-Iron Milano Fit Mini-Madras Sport Shirt
$85 – TopMan SELECTED HOMME Navy And Grey Check Button Down Shirt

Crewneck Sweaters

On warmer days, you can ditch the crewneck sweater and just wear a collared shirt.

$298 – Brooks Brothers Golden Fleece 3-D Knit Fine-Gauge Merino Wool Crewneck Sweater
$158 – J.Crew Lightweight Italian Cashmere Crewneck Sweater (in heather dove)
$40 – TopMan Grey Ripple Textured Raglan Slim Fit Sweater 

Chinos

As for chinos, Spring and Summer is when you pull these bad boys out or you can swap them for a pair of dark wash jeans as well.

Make sure, that you know how either your chino pants should fit or how your jeans should fit, based on your body type.

$75 – J.Crew Broken-In Chino in 484 Fit
$30 – Uniqlo Slim Fit Chinos
$30 – H&M Chinos Skinny Fit

Shoes

Lastly, the brown suede chukka boots in the image are great, but you can also swap them out for brown monkstraps or even white sneakers.

$225 – Vince Camuto Branx Two-Eye Chukka 
$175 – Johnston & Murphy Conard Cap Toe Chukka 
$75 – Aldo Granges Chukka

Men’s Dress Shoes – Monk Straps, Brogues, Wingtips

Let’s talk about my favorite and what I consider the best men’s dress shoes for Fall and Winter – Monk straps, Brogues, and Wingtips.

Quick note: Wingtips are technically Brogues, so I’ll be lumping them together throughout this article. Just know when I refer to Brogues that I also mean Wingtips.

I prefer these during the cooler parts of the year because they go much better with the heavier wool and cotton items you wear in your Fall and Winter outfits. Don’t get me wrong, they also work year-round, but I think there’s better options out there for the other parts of the year. Check out my Summer Essentials Ebook and Wardrobe Essentials Series for details about those options.

Below are the things I look for in a good pair of Monk Straps or Brogues.

MATERIAL

As I said in my Fall/Winter boots story, I love a good calf skin. Don’t get me wrong, I love a suede monk strap or brogue, as well, but if you live in an area with snow or rain, you’ll regret the day you wear them outside. So let’s wait to get into those until Spring or Summer.

SHAPE

I will say this about dress shoes until the day I die, but you want a nice, slim profile with a rounded toe box. Ain’t nobody got time for square or large, bulky toe boxes! – See the video near the top of the article if you’re unsure about what they look like.

COLOR

As for colors, I love a nice dark chocolaty brown, or even a medium brown, like a walnut. Black is also good, but the first color I’d get is brown because it goes better with all the Fall colors in your wardrobe. All these colors are represented in my suggestions at the bottom of this article.

SOLES

If you live somewhere with a bit of rain, ice or snow, then you can and should definitely have these with Dainite or rubber inset soles for added traction. If you don’t live in that kind of climate, then a regular leather bottom that you’ll find on 99% of dress shoes is perfectly acceptable, but I’d probably look for a Dainite or rubber insert sole as my default. There’s also lugged soles, which are pretty popular right now (and I included some in my selects below), but I have a feeling they won’t be around for the long haul. They’ve already come and gone with fashion a few times in my lifetime. When it comes to Fall/Winter boots, though, I love me a lugged sole.

MONK STRAP SPECIFICS

I prefer a double buckle because a single buckle looks less refined. (Example in the video at the top).

If you get black Monk Straps, make sure the buckle is silver, because gold or brass tends to look gaudy, but is perfectly fine on brown monks (examples in the video).

Also, please make sure the buckles are on the smaller side as opposed to some big ass buckles you’ll find on a colonial gentleman.

As for medallion toes and other flourishes, I like all of them, so check out my recommendations below.

 

Best Ways To Wear Dress Shoes

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H&M Blazer Slim Fit
Burberry White Slim-Fit Poplin Dress Shirt
The Tie Bar Navy “Score Check” Tie
The Tie Bar Olive Green 1″ Tie Bar
The Tie Bar Grey Southeast Plaid Wool Pocket Square
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Dress Belt
Allen Edmonds Black Strand Dress Shoes
Tom Ford Snowdon Sunglasses
IWC Portugieser Automatic Watch

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Topman Light Brown Wool Rich Formal Coat
Burberry Slim Fit Cotton Poplin Dress Shirt
The Tie Bar Webster Medallions Tie
J.Crew Slim Merino Wool Cardigan
John Varvatos Grand Sunglasses
J.Crew Ludlow Suit Pant in English Donegal Tweed
Johnston & Murphy Nolen Double Monkstrap Shoes

Brogues & Wingtips

Budget Friendly

$130 – Aldo Bartolello
$165 – Johnston & Murphy Jennings Wingtip
$195 – Vince Camuto Tallden – Wingtip Oxford (2 colors)
$225 – Vince Camuto Benli Oxford

Designer

Allen Edmonds Strand Brown Cap Toe

$395 – Allen Edmonds Strand Cap-Toe Brown Oxfords with Dainite Rubber Sole

These, to me, are the quintessential Brogue. If you’ve seen my other dress shoe article then you know my love of Allen Edmonds. They make amazing products with great value – and they don’t pay me to say that. I’m just a huge fan.

I love this color and the Dainite soles. They’re just perfection.

$395 – Allen Edmonds McAllister Wingtip with Dainite Rubber Sole
$395 – Allen Edmonds Strand Cap-Toe Black Oxfords with Dainite Rubber Sole
$650 – Church’s Toronto Cap-Toe Oxford Brogues
$780 – Prada Runway Hybrid Wing-Tip Oxford 
$1,990 – Tom Ford Austin Cap Toe Oxford Shoe 

Monk Straps

Budget Friendly

Johnston Murphy Nolen Double Monk Strap Brown

$185 – Johnston & Murphy Nolen Double Monk Cap Toe

These hit all the points I look for in a double monk – the beautiful chocolaty brown with the matching soles, the silver hardware and the rubber tread inset for added traction. On top of that, they’re a GREAT price and my clients always comment about how comfortable they are. My other favorites are the Allen Edmonds Monks below, if you’re looking for something higher quality.

$99 – Kenneth Cole Regal Bearing Leather Monk Strap Dress Shoe (2 colors)
$160 – Aldo Caresien 
$225 – Vince Camuto Briant Double Monk Strap Shoe (2 colors) 

Designer

Allen Edmonds St Johns Black Double Monk Strap

$395 – Allen Edmonds St. Johns Black Double Monk Strap 


$395 – Allen Edmonds St. Johns Brown Double Monk Strap  
$395 – Allen Edmonds Mora 2.0 (3 colors)
$435 – Crockett & Jones Lowndes (2 colors) 
$700 – Brooks Brothers Peal & Co. Double Monk Strap

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.

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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

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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

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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 5 Shoes Every Man Should Own

In my Men’s Wardrobe Essentials Series, as well as my Summer Essentials Ebook, I touched on shoes a little bit, but the most-requested video/article for a while has been the number and type of shoes every man should own.

So here it is: These are the quintessential shoes that every man should have in his closet for year-round wear. Anything outside of these are specialty items, like snow boots, so they’re not included in this article.

Have questions? Curious what others think?

Join us in the comments section of the video above.

1. Athletic/Running Shoes

Nike Roshe FlyKnit - Grey

Buy the Nike Roshe FlyKnit in gray

There’s nothing better than a sleek pair of athletic shoes. Not only can they function as your gym shoes, but they can  be worn with your casual outfits, as well.

I recommend sticking with a black/white, black/grey/white (like above), or navy/white color to ensure that your sneakers compliment all your outfits. Other crazy colors like neon green or a bright red will only draw attention away from your outfit which is why I’m not recommending those colors. You probably wouldn’t know it, but these shoes are one of my clients and almost a year old.

Since all of the shoes I’m recommending have white soles, I highly recommend Jason Markk’s Essential Shoe Cleaner Kit. Just give the soles a quick scrub with the included brush and soap every few weeks and they’ll look good-as-new for a long time.

Other Options

Nike SB Stefan Janoski Max
Adidas Pureboost LTD Shoe
Nike Roshe Two FlyKnit

 

2. White Sneakers

 

Buy the Adidas Stan Smith Sneakers

The second pair of shoes you should own, is what I’d consider an absolute essential to any well-dressed man’s wardrobe, which is why they were also included in my Men’s Wardrobe Essentials series.

They’re clean, classy and look great with a lot of your casual, even up to a little more dressy, outfits. Throw on a nice fitted blazer and some dark wash jeans with them and they’ll look amazing. See here for outfit inspiration images.

Under no circumstance should you wear these with a suit, though. That’s a trend that’s been floating around for a few years and I just think you’re not doing a suit justice by dumbing it down with sneakers.

A quick note, because it’s been brought up in the comments of my White Sneaker Video – Jordan’s and Air Force Ones are not the same as these – even if they’re white – because the shape and profile of those shoes are completely different. Notice how sleek and simple the profile of the above shoe is – THAT’S what makes all the difference. Jordan’s and Air Force Ones are chunky looking and have a very specific look that a lot of men can’t pull off.

Designer Options

 

Saint Laurent leather sneakers
Acne Studios leather sneakers
WANT Les Essentiels de la Vie leather sneaker
Common Projects BBall leather sneakers

Budget-Friendly Options

Converse Chuck Taylor All Star II Ox’ Canvas
Converse Jack Purcell Sneaker
Nike Tennis Classic Ultra Leather
Vans Authentic Sneakers

 

3. Suede Driving Moccasins

 

Tod's Gommino Driving Shoes in Suede

Tod’s Braided Tie Drivers

The third pair of shoes you should own are suede driving moccasins. I’ve already covered these in my Summer Essentials Ebook, but they’re also great shoes during the other parts of the year, depending on your climate.

If you’ve never worn a pair, then you really should try them because they’re the most comfortable middle ground between a dress shoe and a sneaker and after they’ve been broken in a little bit, they’ll feel like you’re wearing a pair of socks.

I have these ones here by Tod’s that I really love. Stick with dark brown first, then you can add a tan color and then navy which will cover you for any outfit you can wear outside of a suit – which you should never wear driving mocs with. The construction is fantastic and they hug your feet nicely –
which is important because a lot of cheaply made driving mocs tend to look loose around your feet which is to be avoided.

There’s three things to remember about driving moccasins:

Only wear no-show socks with them. I did a whole video about socks so check out the link in the video description.
Before you wear them for the first time, make sure you Scotchguard them in order to protect the suede from dirt & liquids as much as possible.
They’re going to get dirty, it’s inevitable with suede. So buy them knowing they’re going to have a shorter shelf life than the rest of your shoes, but trust me, you won’t care because they’re so damn comfortable.

Designer Options

Tod’s Textured Suede Tie Drivers
Tod’s Braided Tie Drivers
Prada Suede Slip-On Moccasin, Oltremare
Brook’s Brothers Suede Driving Mocs

Budget-Friendly Options

Jack Erwin Parker Driving Loafer 
FRYE Russel Venetian
Johnston & Murphy Perforated Driving Loafer 

4. Oxford Or Derby Dress Shoes

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Prada Plain Toe Blutchers

The fourth pair of shoes you should own are Oxford or Derby dress shoe with a sleek profile and round toe. I’ve covered these extensively before, but every man needs at least a black and possibly brown pair of dress shoes in his wardrobe. They go well with all outfits outside of a super casual outfit (think: t-shirt and jeans). And since you should at least own one suit, these are necessary because you can’t get away with wearing any other shoes with your suit. Remember: the goal is to have you looking amazing, no matter the scenario or outfit.

I prefer plain toe, but you can also get cap toes, but I will grab a pair of plain toed Oxfords or Derbys over any other kind of dress shoe 99% of the time.

As for brogueing, burnished toes, oxblood or other unique colors, don’t get me wrong, I love them, but that’s like two levels down the road if you’re new to dressing better. They’re very specific and won’t go with a lot of your outfits, so grab them after you’ve invested in a classic black and dark brown oxford.

Designer Options

Giorgio Armani Plain-Toe Patent Leather Bluchers
Allen Edmonds Park Avenue Cap-Toe Oxfords
Allen Edmonds Carlyle
Prada Plain Toe Blutchers

Budget-Friendly Options

Aldo Craosa 
Jack Erwin Joe Cap-Toe Oxford
Johnston & Murphy Hyde Park ll Cap-toe

5. Brown Leather Boots

Purdey Brown Men's Grain Leather Boot With Dainite Sole

Crockett & Jones Islay Wingtip Boot

The final pair of shoes – in this case – boots you should own are a pair of brown leather boots.
They’re utilitarian in that you can wear them in a lot of adverse weather situations as well as in more elevated casual outfits. I prefer brown because boots are usually more geared toward the cooler months, and brown is a great fall/winter color and it goes AMAZINGLY well with the dark wash jeans and wool trousers you should already own. But don’t be mistaken, you can also wear these year-round.

It’s been asked this a few times by viewers, so unless you’re going for the lumberjack or American/Japanese worker-style look, don’t wear these boots with a suit because these ARE NOT DRESS BOOTS.

I love the pebbled brown leather and goodyear welting of the Purdey boots above, which is why they’re my top choice. Trust me, I spent a lot of time finding the best boots out there and these are hands down my favorite.

If you want to know how to tie your boots properly like this so don’t have a bunch of excess laces flopping around, check out my video about how to properly tie men’s shoelaces.

Designer Options


O’Keefe Algy Split-Toe Weatherproof Pebble-Grain Leather Boots
Crockett & Jones Islay Wingtip Boot

Frye Jones Lace Up Boots

Budget-Friendly Options

Aldo Acerrassi
Johnston & Murphy Karnes Cap Toe Boot
Aldo Etausen Boots
Wolverine 1000 Mile Boot 

Chino Pants

Chino pants should be a staple in every man’s wardrobe. They are among the most versatile of men’s pants—they look great with a t-shirt, a sweater and button-down, or can be dressed up for a business casual event. They’re the perfect alternative to jeans since they are more comfortable and breathe easier. This is especially true in warmer weather due to the soft, worn-in cotton twill fabric that breathes easier than denim. And when you want to inject some color into your wardrobe, chinos provide an excellent avenue for this.

The Chino Pants Rules Most Guys Break

I see a boatload of guys making the following mistakes, so I want you to be aware of them:

  • Do not wear or own black chino pants. You’ll look like a waiter or valet guy.
  • Chinos are not dress pants or trousers. They’re the middle ground between casual and formal and should not be worn for anything above a business casual event.
  • Unless you know what you’re doing, stick to pairing them with a polo or dress shirt, v-neck sweater, or harrington jacket. Pairing them with a blazer or suit jacket will go horribly wrong if you’re not sure about what you’re doing.
  • Chinos should be worn with a quarter or no break. They can even be worn at ankle length in some cases, but never, ever longer than a quarter break.
  • Chino pants do not have extra pockets on the legs, hammer loops, stitching, etc. Those aren’t chinos, no matter what their name says.
  • Don’t wear pleated chinos. See the pleats section below for an explanation of why you should never wear them.
  • Pressed creases on the legs are the devil’s work. Don’t ever buy them like this or add them yourself.
  • The same goes for pre-cuffed hems. Don’t wear them, please. You can roll the cuff later on, but don’t buy the ones that come pre-cuffed.
  • To see more style mistakes that men make and how to fix them, click here.

What are Chinos?

The word “chino” means “toasted” and is derived from Latin American Spanish. Chino pants are named after the cotton twill fabric they’re constructed from, often called Chino Cloth. Another distinguishing characteristic is that chino pants will also usually have side-loading pockets, which are different than the traditional front or top-loading pockets as traditionally found on jeans.

Khaki vs Chino

In the most simple terms possible: Khaki is a shade of brown. Chino is a type of pants and called this because they’re usually made from Chino cloth.

The original khaki (light brown) is the traditional and most popular color, but chinos are come in many shades. See my color preferences for men below.

To pleat or not to pleat

As I said in my wool trouser article, I frickin’ hate pleats with a passion.

I don’t care how old or young you are or what your body type is – whether you’re thin or a larger guy, you should NEVER, EVER have pleated chino pants. Honestly, I f*#@%ing hate them because they’re so unnecessary and are unflattering on every guy. I’ll be the first to dance on their grave if they ever completely go away. I’ve never seen a guy look good while wearing them – ever.

To Cuff & Crease or Not

You can, and sometimes should, cuff or roll up chino pants. But don’t ever buy a pair of chinos that are pre-cuffed. It’ll be very hard to get that crease out and the hem will likely be very thick, which won’t look that great.

As for creasing the front the of leg, if you’re looking at a pair of chinos that’s creased like this, run for the hills! They should never be creased like dress pants because… repeat after me: They’re not dress pants.

What colors should you get?

You should at least have two colors of chinos because they’ll pair well with all the other items in your Essential Wardrobe. A quick note about colors: Whatever you do, make sure the colors you choose are not too shiny or glossy looking. You’ll know it when you see it. You want a more matte finish to your chinos.

  • Sand – I prefer this lighter brown/tan color than the darker, flatter khaki color. Some brands will call sand colored pants khaki, so just go for lighter brown colors regardless of what the brand calls them. The model in the image at the top of this article is wearing, what I’d consider, the perfect sand color. Shoot for something similar.
  • Navy – Whatever you do, just don’t get such a dark navy that it looks black. That’s a big no-no. The navy in my first “Best Ways To Wear” image below is what I’m talking about.

If you already own these colors and want to add more, then go for gray/charcoal or an olive color. If you want to try other colors, just make sure you understand what colors work best with your skin tone.

The Best Chino Pants For Your Body Type

Slim or Regular Build

You’ll want to get a “Slim” fit chino pant that will hug the thighs, knees, and calves while tapering down from your knee to ankle.

A lot of my slim & regular built clients initially believe this style will make them look too skinny. This couldn’t be further from the truth. It’s just that they’re used to wearing super baggier clothes to try and hide their slimness, which, coincidentally, just makes them look slimmer. A proper fitting pair of chino pants just looks right, regardless of your build, and doesn’t make you look one way or another – I promise.

Determining the ideal cut of your chinos depends on your physique.

If you’re a heftier guy or have larger thighs, I recommend a straight leg chino. It will give your body a trim, well-proportioned appearance. Slim fit chinos that taper slightly in the leg will make you look somewhat imbalanced—giving you a top-heavy look with skinny legs. Unless you’re on the shorter side, then a slight taper is OK, but under no other circumstances should your chinos be tapered.

Larger Build

The classic “Straight-Leg” fit is perfect for you. No matter a man’s build, but especially in your case, it’s all about balancing your body’s proportions to make sure your bottom half complements your upper half. So stick to this cut of chinos for your physique and you’ll look fantastic.

HOW SHOULD MEN’S Chino Pants FIT?

See my Chino and Khaki Pants Fit Guide for details.

The Best Chino Pants for Men

Designer Options

I’m a huge fan of each of these designer’s chinos as the construction, quality, and fit are spot on. You won’t go wrong with any of these, but just remember to choose the right fit for your body type.

Rag & Bone Fit 2 Navy Chino

Rag & Bone Fit 2 Stone Chino

A.P.C. Truck Stretch-Cotton Twill Chinos

Brooks Brothers Red Fleece Navy Slim Fit Chino

Burberry Straight Fit Taupe Chino

Budget-Friendly Options

If you’re on a budget, all three of these are great. Each brand offers a few color choices, which are usually the typical khaki, navy, and gray. A great thing about Uniqlo is that they offer free hemming service so there’s no excuse to have your chinos be too long 🙂

H&M Beige Chino Slim fit

JCrew Straight Fit ‘1040’ Navy Chino

Club Monaco Connor Slim-Fit Stretch-Cotton Twill Chinos (Ecru or Midnight Blue)

3 Ways to Wear Chino Pants

(Sunglass lenses sold separately)

H&M Polo Shirt

H&M Chinos Slim Fit

Vans Authentic Sneakers

True Vintage Revival Glasses

Ashley Weston Chino Pants Sport Coat Polo Shirt

 

Brunello Cucinelli Charcoal Textured Two-Button Wool Blazer

Tom Ford Navy Short-Sleeve Polo Shirt

Brooks Brothers Khaki Milano Fit Plain-Front Lightweight Advantage Chinos

Salvatore Ferragamo Brown Textured Calfskin Penny Loafers

The Tie Bar Navy Cotton Table Plaid Pocket Square

IWC Portuguese Automatic Watch

Ray Ban Aviator Light Ray ll

Polo-Shirt-Outfit-2-Ashley-Weston-Mens-Wardrobe-Essentials

Philipp Plein Coat So Cool

Tom Ford Short Sleeve Pique Polo Shirt

Brooks Brothers Slim Fit Dark Khaki Garment-Dyed Chinos

Nike Tennis Classic AC ND

Allen Edmonds Black Poplar Belt 

IWC Portuguese Automatic Watch

John Varvatos Bowery Square Polarized Sunglasses

Outfit Inspiration

 

The #AskAW Show: Episode 02

Have a question you’d like me to answer? Ask in the comments of this youtube video or send me an email.

Show Notes & Links

Q: I’d like to find a good pair of suede Chukka Boots, but I’ve got big feet – Size 15, can you help?

Allen Edmonds - Dundee Suede

Allen Edmonds – Dundee Suede

 

Q: What can I wear with my blue suede wingtips?

Dark wash jeans 

 

Q: How can I dress nicely in really warm weather?

Polo Shirts

 

Linen Button Up Shirt

 

Chino Pant

 

Shoes

 

Q: What watches would you recommend for a guy with skinny wrists who wants a brown band?

 

Q: What do you think about the proportions of this jacket?

Fashionbeans.com story I commented on.