5 Men’s Shoe Styles Women Hate

It’s a fact that one of the first things a woman notices about you is your shoes.  So obviously it’s important to make sure your shoe game is on point. We always talk about how important it is to regularly clear out old and out of style items, and shoes are no different.  Shoes are a key part of your overall look, and a few wrong choices or out of date items can easily ruin an otherwise great look. 

Here are Ashley’s picks for 5 Men’s Shoe Styles That Women Hate!

5 Shoe Styles Women Hate

  1. Square toed dress shoes
    Out of date and out of style, get rid of them right now. Get yourself a proper pair of dress shoes instead.

4. White loafers or loafers with contrasting stitching
Your loafers should always have same-color stitching and white loafers are another out of date style nobody should wear. Try our Loafer Guide for better options.

3. Chunky basketball/gym sneakers
The gym or basketball court is fine but outside of that, these shouldn’t be worn with casual clothing. White sneakers or dress sneakers are a much better look.

2. Rubber flip flops
Unless you’re at the beach or pool these aren’t a good look.

1.Slides
Keep them to the bathroom or inside the house, nobody should see these!

3 Boot Styles Every Man Should Own For Fall/Winter 2018

Boots are a fall/winter staple and the right pair (or two) should be versatile enough for a variety of outfits and occasions. I think Chelsea boots are more of a spring/summer style so we’re focusing on shoes that will get you through the colder, wetter months of the year and work better with heavier clothing.

One thing to remember, look at boots as an investment, good ones aren’t cheap, but properly taken care of they can last you many years. There are a ton of options out there and we’ll include our picks, but we’ve narrowed it down to three basic styles that you should have in your closet.

Desert/Chukka Boots

The most versatile and least seasonal, you can wear these nearly year round. They’re light and comfortable and work well with both casual looks (jeans, chinos) and more dressy looks (with sweaters and blazers).

Picks

Zegna

Allen Edmonds

Clark’s

Budget-Friendly Clarks

Johnston Murphy #1

Johnston Murphy #2

Work Boots

What you probably think of when you think of boots, these are more rugged and have thicker/chunkier soles. The look great with jeans and chinos and will get you through the colder months and weather with ease. They can come in a variety of styles, some very casual, others a bit more dressy.

Picks

O’Keefe

Red Wing Beckman

Allen Edmonds #1

Allen Edmonds #2

Wolverine 1000 Mile

Danner Jack

Dress Boots

Yes, you can and should dress up your boots. Just make sure you’ve got the right styles. Think of these like the hightop versions of your dress shoes. They should have a thinner, dressier sole and nice leather. Look for them in cap toe or wingtip versions. Formality note: some dressier styles come with a bit more tread (called a lug sole) which can still look good with dressier clothes, but it will make them slightly less formal.

Picks

Edward Green

Brooks Brothers Peal & Co.

Grenson

Mezlan

Allen Edmonds #1

Allen Edmonds #1

Aldo 

Calvin Klein

The Essential Business Casual Details & Outfits

To me, business casual for men’s outfits is a loose definition, but it definitely has an upper and lower range of what’s appropriate. The only true way to determine what it means is by looking at it in relation to the current dress code of the company or function you’re dealing with.

Things to avoid in business casual

Ties

There are rare exceptions, but when in doubt, go without.

Shorts

These are too casual no matter how they’re worn and I’d argue that a man shouldn’t wear shorts in 95% of situations, anyways.

T-Shirts

While I love them, they have no place in a business casual outfit.

Not Tucking In Your Shirt

The sin of all sins for a business casual outfit, no matter your body type, is not tucking in your collared shirts. Polo shirts should only be worn untucked, but the exact opposite is true for collared shirts. It just looks sloppy.

 

Now let’s go over the typical outfits and when they’re appropriate to wear.

Standard Business Casual

For most companies, whether they require a suit (maybe no tie) or a blazer or collared shirt everyday, there are two types of business casual outfits. How close the dress code is to a full suit will determine whether you should wear a jacket or not. Also, depending on the time of year, you may go for lighter or heavier weighted fabrics for your jackets and pants. Hotter = lighter.

With A Jacket

If you are required to wear a suit and tie everyday, definitely go with this one.

Sport Coat/Blazer

Here’s another article I wrote about heavier sport coats/blazers for the Fall & Winter months. Please, whatever you do, don’t wear a suit jacket in place of this. The fabric is too thin and it won’t match the fabric weight of the pants you’ll be wearing.

Oxford Button Down Shirt or Semi-Spread Collared Shirt

Make sure either of these are tucked in to your pants. Definitely wear a belt that matches your shoe color, as well.

Wool trousers, Chino Pants or Dark Wash Jeans

The more formal the dress code, the more likely you should wear wool trousers. Chinos are a little less formal or more used during spring and summer, while jeans a little less so than chinos and typically used year-round. Never, ever – unless the suit pants are a very thick wool (similar to wool trouser weight) – should you wear suit pants without the accompanying jacket.

Oxford Dress Shoes, Monk straps, Brogues, WingtipsBoots (Dress or Chukka) or Loafers

The second you’re not wearing a full suit and tie, you can basically wear anything but sneakers with your business casual outfit. I’d default to Oxfords, Monk Straps or Loafers – either in suede or leather, but any of the options above are acceptable.

Without a jacket

If the dress code or occasion is slightly more casual, you can forgo the jacket and wear this business casual outfit, instead. There’s a few small points to consider.

V-neck sweater

If the weather is too warm, then definitely swap out the sweater for a blazer from the previous section, or, if it can be more casual, go to the next outfit, instead.

Shirt

Same as the previous outfit. You can wear a tie, like in the above picture, but it’s not necessary at all.

Pants

Wool trousers or dark wash jeans. Chino pants have a fabric weight that is too light to go well with v-neck sweaters.

Shoes

Same as previous outfit.

 

Casual Business Casual

This type of business casual outfit is appropriate if there’s a pretty casual dress code normally, or the event is very informal. If you see “business casual” as a requirement anywhere, this is the least formal outfit you can wear that is still appropriate for the dress code. Anything less than this is not business casual.

Harrington Jacket 

This is one of my favorite jackets of all time and fits this outfit perfectly. Obviously, only wear this if the weather is requiring a jacket.

Polo Shirt or Oxford Button Down

I’d probably default to a polo shirt unless you knew for a fact you were going to wear the Harrington Jacket or the weather is cooler. Unless you’re a slimmer guy, an Oxford Button Down worn without a jacket on top of it doesn’t look too good. No matter what, though, make sure the polo shirt fits like a glove or you’re going to look like a goofball and if you wear the oxford, please tuck it in.

Chino Pants or Dark Wash Jeans

Chino pants are the default in an outfit like this, but dark wash jeans are just as appropriate. I’d let the time of year or weather dictate whether I went with chinos or dark wash jeans. The colder it is, the more I’d lean toward wearing the jeans over the chinos.

Sneakers, Loafers, Dress Shoes or Chukka Boots

The more classy you want to make this casual outfit, the more I’d learn toward dressy shoes.

 

That’s it! Hope this is helpful!

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.

Snorkel / Parka Jacket

Because of all the rain that’s been happening here in LA and the East Coast, I’ve been trying to find stylish yet practical jackets for some of my clients who are doing press right now along the soggy coasts. I found this awesome snokel jacket that fit the bill perfectly.

 

 

Snorkel Jacket POTW Ashley Weston

Jacket

I was so excited to find a lightweight snorkel jacket that fit the bill perfectly. A snorkel jacket is basically a parka. It’s a 3/4 length jacket hitting mid-thigh and has a drawstring hood that can tighten so your entire face is covered except a small breathing hole, hence the name snorkel. A lightweight jacket, like the one in the image, will also take you through Spring and is easy to layer under.

$788 – Todd Snyder Storm Parka in Beige
$298 – J. Crew Lightweight Snorkel Jacket
$150 – Zara Technical Parka

Shirt

In the image, the jacket is layered over a striped long sleeve shirt, but you can also wear a grey, navy, or burgundy sweatshirt or crewneck sweater.

$168 – Todd Snyder Italian Silk-Cotton Striped Sweater
$95 – Vince Striped Long Sleeve T-Shirt
$60 – J. Crew Striped Long Sleeve T-Shirt in Heavyweight Jersey
$35 – TopMan Selected Homme Navy and White Stripe Long Sleeve T-Shirt

Jeans

Not only does this outfit look great with some dark wash jeans, you can also wear a pair of chinos or wool trousers with it.

$228 – JBrand Tyler Taper Fit in Rasalas
$70 – Levi’s 511 Slim Fit Stretch Jeans (Blue Flame or Dark Hollow)
$40 – Uniqlo Stretch Selvedge Slim-Fit Jeans

Shoes

As for shoes, I’d go with a pair of boots or sneakers.

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.

plaincaptoebroguingashleyweston

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.

mensleatherbootsolesashleyweston

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

fallwinteressentialsbootsashleywestonoutfit2

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 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

ferragamo-marte-plain-toe-derby-ashley-weston1

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 

Steven Yeun Style

This article & video is part of the Celebrity Style Inspiration Series, where Antonio Centeno from RealMenRealStyle.com and I pick out great outfits from actors from movies and tv shows and demonstrate how to recreate and incorporate them into your wardrobe. 
In the other video/article, currently live on RMRS Channel & Website, we talked about Steven Yeun’s style from The Walking Dead, but I don’t think a lot of people know that Steven’s off-screen style is also very, very good. He’s one of the few male celebrities that I know who doesn’t use a stylist who looks amazing all the time. I’ve worked with him quite a few times over the years and he’s definitely one of the naturally best dressers I know – and a total sweetheart!

When I was deciding on which of his outfits to feature, I found this one from a red carpet appearance and loved it, so I texted to let him know that I was going to do a video about it. He said he was excited to see how I’d recreate it, so… Hi Steven! 

Below is Steven’s outfit I’m going to recreate for you. I specifically like this because it’s casual but has just the right blend of edginess to it with the boots and cuffed pants.

The Jacket & Sweater

I like Steven’s cardigan jacket a lot, but I prefer a bomber-style jacket instead (in my model image below) because not only does it look great on all body types, it also helps break up the top and bottom halves a little bit more with the black waistband, which also lends itself well to the cuffed pant and chelsea boot look. I had my model wear a plain white t-shirt underneath the sweater because it provides an extra layer of warmth and adds a nice little neutral accent just peeking through. 

Pants and Shoes

StevenYeunBottomHalfAshleyWeston

I added some dark wash jeans to stay true to the outfit and even though suede shoes are not my preference for most men, I went with similar suede boots because they work very well in Steven’s outfit. I especially love my choice because it’s a nice dark brown suede, which is easier to wear than a more reddish-oxblood brown or a lighter brown like Steven’s boots. My color choice will also look a little cleaner longer since it won’t show as many stains. 

And, of course, you’ve got to cuff/roll the jeans to complete the look.

My Version of this outfit

Topman Khaki Tailored Jersey Bomber Jacket (the original jacket I used isn’t available anymore, so this was the closest I could find from the same brand)
Life After Denim Heather Grey Astoria Crew Sweatshirt
Armani Exchange White Pima Crew Neck Tee
J Brand Tyler Slim Fit Stretch in Tumble
Vince Camuto ‘Bradbury’ Chelsea Boot

 

Designer Options

Frame Cotton Bomber Jacket 
Rag & Bone Depot Jacket
Acne Studios College Loopback Cotton-Jersey Sweatshirt
Sunspel Loopback Cotton-Jersey Sweatshirt
James Perse Short Sleeve Crew Neck 
Jil Sander Slim-Fit Cotton-Jersey T-Shirt
Burberry Brit Slim-Fit Washed Stretch-Denim Jeans
RRL Slim-Fit Selvedge Denim Jeans
John Lobb Lawry Suede Chelsea Boots
O’Keeffe Bristol Suede Chelsea Boots

Budget Friendly options

ASOS Jersey Bomber Jacket With Contrast Ribs in Khaki
Topman Khaki Cotton Bomber Jacket
H&M Gray Melange Sweatshirt 
Selected Homme Sweatshirt
American Apparel Fine Jersey Crewneck T-Shirt
Armani Exchange White Pima Crew Neck Tee
Uniqlo Stretch Selvedge Slim Fit Jeans  
Levis 511 Slim Fit Stretch Jeans in Sargent Cypress
ASOS Chelsea Boots in Suede
Johnston & Murphy Garner Gore Boots

Outfit Inspiration For Chelsea/Suede Boots & Bomber Jackets