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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 Charcoal Wool Blazer
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 Black Poplar Dress Belt
Allen Edmonds Black Strand Dress Shoes
Tom Ford Snowdon Sunglasses
IWC Portugieser Automatic Watch

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Topman Camel 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
$135 – Johnston & Murphy Duvall Wingtip (2 colors)
$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
$580 – Salvatore Ferragamo Oxford Shoe
$650 – Church’s Toronto Cap-Toe Oxford Brogues
$700 – George Cleverley Henry Pebble-Grain Leather Wingtip Brogues (2 colors)

 

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)
$130 – Aldo Henacien
$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) 
$710 – Crockett & Jones Harrogate Double Monk Strap 

5 Shoes Every Man Should Own Ashley Weston

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.

 

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 Ultra Boost Shoes
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 SL/01 Court Classic Sneakers
Acne Studios ‘Adrian’ White Sneakers
WANT Les Essentiels ‘Lennon’ sneaker
Common Projects ‘BBall’ Leather Sneakers

Budget-Friendly Options

Converse Chuck Taylor All Star II ‘Ox’ Canvas
Converse Jack Purcell Jack Sneaker
Nike Tennis Classic Ultra Leather
Vans Leather Old Skool Reissue DX

 

3. Suede Driving Moccasins

 

Tod's Gommino Driving Shoes in Suede

Buy these Tod’s Gommino Driving Shoes

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 Gommino Suede Driving Shoes
Tod’s Gommino Driving Shoes in Suede
Salvatore Ferragamo ‘Parigi’ Moccasin
Brook’s Brothers Suede Driving Mocs

Budget-Friendly Options

Aldo Zurlo Navy Suede Loafers
ASOS Loafers in Brown Suede
Aldo Clemens Suede Tassel Loafers
TopMan Suede Driving Loafers

4. Oxford Or Derby Dress Shoes

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Buy the Salvatore Ferragamo ‘Marte’ Plain Toe Derby

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

Salvatore Ferragamo Remigio Cap-Toe Oxford
Allen Edmonds Carlyle Black
Allen Edmonds Carlyle
Christian Louboutin Top Daviol

Budget-Friendly Options

Aldo Thunder Dress Shoe
Aldo Thunder Dress Shoe
Johnston & Murphy  Hyde Park ll Cap-toe
Johnston & Murphy – Hyde Park ll Capt-toe

 

5. Brown Leather Boots

Purdey Brown Men's Grain Leather Boot With Dainite Sole

Buy These Purdey Brown Men’s Grain Leather Boot With Dainite Sole

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

Purdey Grain Leather Boots
Crockett And Jones Galway 2 Apron-Toe Boot
John Lobb Alder Boots
Frye Jones Lace Up Boots
Red Wing for Brooks Brothers 4556 Iron Ranger Boots

Budget-Friendly Options

Johnston & Murphy Karnes Cap Toe Boot
Aldo Etausen Boots
Timberland Earthkeepers Rugged Waterproof Boots

Men's Summer Essentials ebook Ashley Weston

Men’s Summer Essentials Ebook

In this ebook, I’ll detail the items you need for summer, why you need them, and where to get them – in designer and budget-friendly options.

These items will work very well with the rest of your year-round essentials, so if you haven’t seen that series, check it out first.

My goal is to ensure you’re comfortable, wearing appropriate colors and items for the season, while looking amazing and not like a douchebag.

So download the book, pour a glass of… something (I prefer rosé) and let me show you the good stuff!

Summer Essentials
First
Last
Sending
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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. 

 

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The Oxford Dress Shoe

This article is part of my Men’s Wardrobe Essentials series.
These are the best mens dress shoes, no questions asked. Anything else pales in comparison. Every man should have at least 2 pairs of Oxford dress shoes in his closet. Not only are they one of the most versatile shoes a gentleman can own – which will work for nearly all formal occasions from business casual to formal – but they’re the de-facto standard shoes to wear with a suit. On top of that, they’ll also work very well with 99% of the items in your Essential Wardrobe. They’re that good.

When you imagine a well-dressed man in a suit, I guarantee he’s wearing a pair of these.

Black & Leather ≠ Oxford Dress Shoes

Don’t think that if a shoe is black and leather, it’s an Oxford dress shoe. I shudder at the thought of those square-toed and/or slip-on monstrosities I see men wearing in place of a proper, lace up, round-toed dress shoe.

Also, if you can see your reflection in your black leather shoes, those are not a proper dress shoe. Those are tuxedo shoes. As the name implies, they should only be worn with a tuxedo. I’ve seen quite a few guys wearing these shoes with jeans. It’s not a good look. Your Oxfords shouldn’t look like mirrors, they should be a little more matte finished. Go to a department store and ask to see their tuxedo shoes so you can see the difference in person.

The image below from RealMenRealStyle highlights exactly what I see a lot of men wearing in place of Oxford dress shoes:

Wrong-Square-Toe-Shoes

To Cap-Toe or Not?

My opinion about whether you should have a cap toe Oxford or not changes with the wind, so I’ll leave it up to you. There’s not a single scenario when you’d wear a cap-toe over a non-cap toe, so this is entirely up to your preference. 

My clients are split 50/50 on this, too. You won’t go wrong with either, so choose whichever you think looks great and fits your style best.

allenedmonds_shoes_carlyle_blackallenedmonds_shoes_park-avenue_black

Should I go for Quality or Value?

For foundational pieces such as these, I’d say go for quality. However, there is a caveat:

How Often Will You Be Wearing Your Oxford Dress Shoes?

  • If you’ll be wearing them more than a handful of times a month, definitely grab a nice, high quality pair. They’ll give you many good years of use and look great the whole time.
  • If you’ll be wearing them once a month or less, go for value. They’ll definitely get the job done and look “good enough”. What’s the use of having a high quality pair of dress shoes sitting in your closet most of the time? I’d take that money and spend it on other pieces you might wear more often](link).

Which Shoes Should I Get?

Since you’ve decided whether you like cap-toe or non cap-toe shoes, now it just comes down to color.

Every guy should have these two pairs of Oxfords in their wardrobe to cover every outfit choice:

  1. A solid black pair
  2. A brown/cognac pair

Anything outside of those two colors will have more specific uses and occasions and definitely falls outside the domain of an Essential Wardrobe item.

The Best Mens Dress Shoes

These are my go-to Oxfords for clients:

Designer Options

Salvatore Ferragamo Cap Toe Oxford  
Allen Edmonds Carlyle Black
Allen Edmonds Carlyle
Christian Louboutin Top Daviol

Budget-Friendly Options

Aldo Thunder Dress Shoe
Aldo Thunder Dress Shoe
Johnston & Murphy  Hyde Park ll Cap-toe
Johnston & Murphy – Hyde Park ll Capt-toe 

2 Ways to Wear

For other ways to wear your Oxford dress shoes, check out my Gray Notch Lapel Suit article, Dark Wash JeanSemi-Spread Collar Dress Shirt & Leather Jacket articles.

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Model: Tommy Mckeown

Fred Perry Reissues Harrington Jacket
Brooks Brothers Red Fleece Shetland Wool Crewneck Sweater
Brooks Brothers Non-Iron Milano Fit Button-Down Collared Dress Shirt
Burberry Brit – Straight Fit Rinsed Japanese Denim Jeans
True Vintage Revival Glasses
Allen Edmonds Poplar Dress Belt
Daniel Wellington Classic Sheffield 36mm
Allen Edmonds Carlyle Plain-Toe Oxfords

BlackOxfordDressShoeLook2640-Ashley-Weston-Mens-Wardrobe-Essentials

Brooks Brothers Red Fleece Topcoat
Brooks Brothers Red Fleece Merino Wool V-Neck Sweater
Brooks Brothers Non-Iron Milano Fit Button Down Collar Shirt
Brooks Brothers Milano Fit Plain Front Trousers
Allen Edmonds Poplar Dress Belt 
Daniel Wellington Classic Sheffield 36mm
Allen Edmonds Carlyle Plain-toe Oxfords

Outfit Inspiration