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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.
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.
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.
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.
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.
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.
The V-Neck Sweater is an essential because you’re going to need warm layering pieces for the cooler parts of the year and it allows you to mix and match your Essential Wardrobe a little better by layering it with a blazer or suit, over an oxford or semi-spread collar dress shirt and paired with simple dark wash jeans or wool trousers and a white sneaker, boots or oxford dress shoes. So how could I leave it off this list?
Crewnecks are okay, but they’re a more casual item. So for this reason, a V-Neck sweater is essential because it’s the classy mofo of the sweater world. V-necks add a touch of dressy formality that you just won’t get with a crewneck.
I love crewnecks, don’t get me wrong, but most guys don’t know how to wear them so then it starts looking really sloppy. I know some guys like the crew neck and tie or suit look, but I would choose a v-neck or cardigan sweater over a crewneck in this case almost every time.
I prefer the V-Neck Sweaters I work with to be made of wool, – either regular or merino wool. Cashmere is also a great fabric, but it’s definitely on the pricier side. If you run a little warmer, then go for a wool/silk or cotton-blended sweater – Pima cotton is also great, but it stretches out very easily.
You need at least 1 black V-Neck Sweater in your closet. If you’ve got a black one already, grab a navy and/or charcoal gray version. These colors will go with everything else in your Essential Wardrobe. If you want a 3rd option, then a darker brown will also go pretty well with your wardrobe, too.
Check out my V-Neck Sweater fit guide for how (all) your sweater(s) should fit.
I love these because the fit, fabric weight, and overall construction is impeccable and I’ve worked with these brands many, many times.
I love each one of these v-neck sweaters, especially the H&M and Life After Denim sweaters. Even though they’re budget-friendly, the quality, fabric weight, and overall fit is really good.
NOTE: A Navy Blazer looks horrible with a pair of tan chinos/khakis. This is the quintessential older, out-of-touch-guy-who-wants-to-dress-up uniform. Just. don’t – Ever.
I see some resources online talking about how a Blazer is different from a Sport Coat/Sports Jacket and honestly, in all my years in the industry, the term is used so interchangeably that it doesn’t matter. They’re basically the same garment. If I have a hard time telling the difference, you’ll have an even harder time, so I say don’t worry about it and call it whatever you want.
The differences between a Blazer and Suit Jacket are constantly debated. A lot of sources say they’re the same, others say they’re different, but allow me to flex my teeny tiny muscles a bit, as I deal with these items day in and day out.
First and foremost, they’re not the same. A Blazer is made of thicker fabric so it pairs better with other clothing items of different weights, like jeans, for example. A Suit Jacket is made of lighter material and should only be worn as part of a suit.
You may not notice, but fabric weights can influence whether an outfit looks off or not. Blazers are not made of the same weight of fabric that a Suit Jacket is.
If you have a chance, go somewhere that requires a jacket be worn – like a business casual event or restaurant that requires a dinner jacket be worn – and I guarantee you’ll see some guys wearing suit jackets with jeans or khakis. I’m sorry to call them out, but older gentleman are the worst offenders here.
I want you to notice how it just looks… weird. The jacket fabric seems a little too “thin” and “flowy” compared to the pants because it’s too light of a fabric to go with a heavier fabric like denim or khaki. They don’t lay or move the same, so it looks weird.
The problem is that most guys see pictures of other guys wearing suit jackets with denim pants and think it looks great, which it does – in pictures. In person it looks bad due to the differing fabric weights. So trust me on this one – you need separate Blazers and Suit Jackets.
Here’s my patented 4-Step process to tell if a jacket is a Blazer or a Suit Jacket:
I recommend you go with a heavier, textured wool fabric because its robust and you’ll get a lot of mileage out of this type of blazer. I like a fabric weight of between 8 to 10 ounces, depending on your climate (hotter climates, I like around 6 ounces). If you go heavier than my recommendations, then you’re getting into Fall/Winter territory and the lighter weight fabric would wrinkle pretty badly. This weight also looks best with the other items a blazer is typically worn with – jeans, wool pants, sweaters, etc. – basically everything else in your Essential Wardrobe. Lighter fabrics have very slim use cases and are a pain in the butt to maintain that they’re usually not worth the hassle.
If you read the title, you know I’m going to say navy :). The reason is because it will go with everything else in my Men’s Wardrobe Essentials list. If you already own a navy Blazer – great job! – then go with a Charcoal or Charcoal Herringbone pattern.
Ideally, you’ll want to go with a double vent. This style of vent has been around for quite a while and is flattering on every body type. With that being said, a single vent is not a poor choice, but it’s definitely second in my book. Just make sure that, no matter what, you never go with a blazer without a vent – it’s a horrible look.
Check out my Blazer/Sport Coat Fit Guide for details.
I chose these blazers because they’re not only well-constructed, but they’re also made of a nice, textured fabric that has the perfect amount of weight to them. Each of these blazers has the 2-button, notch-lapel features that I love and that work on all body types. The navy Brooks Brothers blazer is only offered with gold buttons online, but they do have non-gold button options available in their stores. Stick with their Milano or Fitzgerald lines as they offer the most tailored fits. Ermenegildo Zegna and Z Zegna make incredible blazers that always makes me stop and touch them whenever I’m at the store pulling clothes for a client. Burberry is fantastic for slimmer men that are 5’10” and above.
These are my go-to for blazers that look great, sport all the features I want to see on a blazer, and hit a more affordable price poin. J.Crew offers wool blazers for an extremely affordable price and their Ludlow line has a tailored fit that is fantastic and offered in a range of sizes, from Short to Regular to Tall. If you’re a slim to regular build, I love Topman because their cuts are the best! The material is usually a polyester-wool blend so it’s not the best, but it’ll get the job done and still look fantastic.
If you live in a climate where the temperatures drop during the winter, you’re going to need a coat or two. So let’s talk about Overcoats & Peacoats. They’re not to be confused with a jacket or windbreaker or whatever other sorry excuse for a coat I see guys wearing during the winter months. You need a proper coat that’ll look sharp and timeless and last many, many seasons. Your coat is the first thing anyone is going to see (aside from your shoes and a scarf) during the winter months, so let’s make sure you look amazing.
In my travels, I see a lot of Overcoat blunders, so let me go over the common mistakes I see guys making with their coats before we dig in.
A man should own at least one of these two coats, maybe both. See below to determine whether you need one or both coats in your closet.
There’s two factors to determine whether you should own an overcoat:
Every guy, regardless of his climate or whether he wears suits regularly or not, should own a Peacoat because it’s great for casual outfits in your Essential Wardrobe. If you live in a colder climate, it’s also great for warmer winter days and through the early parts of Spring. Notice I’m leaving out Fall. This is because that’s when a Blazer, Leather Jacket and Harrington Jacket really shine. For moderate/warmer climates, like Southern California, a Peacoat will be your “winter” coat.
A proper Peacoat is always double-breasted, so that’s not an issue.
As for Overcoats, stick to a single breasted coat because a double breasted Overcoat would require you to wear it buttoned 24/7 since it looks really big and floppy when it’s left unbuttoned. Single breasted gives you the option to wear it buttoned or unbuttoned while still looking sharp and form-fitting.
For Peacoats, you want to go with the classic Navy color. For Overcoats, you can go with Navy, Camel (tan), Black or Dark Gray. If this is your first Overcoat, go with Dark Gray or Black. If it’s your second, get a Camel Overcoat to inject some color into your wardrobe, as it’s still a neutral color that will go with the rest of the Men’s Wardrobe Essentials.
Check out my Overcoat & Peacoat fit guide for how a man’s coats should fit.
I chose these coats because they all have a great tailored fit and the material, coat length, lapel width, buttons and the overall construction of them is impeccable. I love the Brooks Brothers charcoal Overcoat, which I actually used on a recent shoot with Harrison Ford, and I was amazed at how well-designed this coat was. The Burberry and Billy Reid Peacoats are my favorite Peacoats of all time! The details are incredible and they’re flattering on every man. An interesting fact: The Billy Reid coat is named the “Bond” coat because it’s the exact one Daniel Craig wore in “Skyfall.” The Burberry runs on the slimmer and slightly longer side, so if you have a shorter and wider build, then this may not work for you, although my model (below) was wearing it and he was quite “built”, so YMMV (your mileage may vary).
Each of these coats has a simple and clean design with no unnecessary flourishes, which you’ll usually find with cheaper alternatives. The price point is great for these considering they’re wool and wool-blended coats and will keep you warm and looking sharp. I love the Topman Camel Overcoat a lot, which is why I used it on my model below!
See my Men’s Wardrobe Essentials articles for the clothing you should be wearing to look more mature. Also, see my Men’s Clothing Fit Guide for how each of these items should fit, regardless of your age or body type.
I’ve seen so many articles and videos taking how to get the proper dress shoe fit that are completely unnecessary and just create more useless work and steps for the poor readers. Of course, if you ask a shoemaker or shoe salesperson about what goes into fitting for a pair of dress shoes, they’ll tell you about the painstaking process you must endure as they pull out their Brannock device and start measuring the length of every toe hair in relation to the current barometric pressure. As someone who dresses and fits men for shoes as part of my career, it’s all hogwash.
Never once, in all my years, with all my clients, have I ever needed to get an exact measurement of their feet – and this is because the brands and manufacturers don’t work this way. Their sizes aren’t universal and can vary wildly between brands. So a 9 in one brand might fit the same as a 10.5 in another brand. Each one is different, so it’s great that you know your right foot is 10.236 inches long by 4.789 inches wide, but that really doesn’t matter unless you’re getting custom made shoes.
So what you have to do is try on dress shoes and figure out how to get the best fit in that style/brand. Let me show you how.
You should know and do these few things before trying on dress shoes.
I’m assuming you’ve worn shoes before and have a general idea of your size? Great! That’s all you need. Like I said earlier, since each manufacturer has different fits and sizing for their shoes, it’ll all be trial and error anyways. The thing you want to do is get in the ballpark and use that as a starting point.
If they don’t, they’ll never fit. Leather, especially in dress shoes, will stretch very, very little, so “working in” a pair of dress shoes is not going to happen and will be a waste of your time and money. One of the worst things ever is wearing a pair of uncomfortable shoes – as a woman, I know this all too well!
So, if you can, try on shoes in the afternoon. This way, you’ll get the most realistic size and fit of the shoes.
Make sure the shoes fit your larger foot first, not the smaller one. Slightly too big is not uncomfortable, slightly too small is very uncomfortable.
When you’re trying on shoes, here’s the things to do and look out for.
Wear the type of socks that you will normally wear with these shoes. In other words, don’t wear your thick woolen socks, or your super thin ankle socks when trying on dress shoes.
If you feel ANY bunching in the toes or feel the shoe pressing against any of your toenails, they’re too short. I see some places talking about your toes grazing the front of dress shoes – this is not correct.
Your feet shouldn’t be touching or grazing anything in the front. If they’re grazing, that means when you walk, your toes will be jammed into the front of the shoe, because your feet will shift slightly forward as you walk, which is very uncomfortable. Either go up a half size and if that doesn’t fix the problem, it might be a style or width issue. So try a different style or a different brand that makes the same style. Luckily, with dress shoes, they’re pretty darn similar, so you’ll find an equally great one, I promise.
The shoe should not be putting any pressure or squeezing on the sides of your foot – anywhere. If you feel anything like that, you may need to go up half a size and see if that fixes the issue. If it doesn’t, you can see if they make a wider size in the same style. If they don’t, then try a different style or brand. Some brands are wider than others.
On the flip side side of that, you also shouldn’t have any room on either side of your foot that allows your foot to move left or right when it’s laced up. If this happens, go down half a size and see if that fixes the issue. If not, you can ask if they have a narrower width in this shoe. If not, you may need to try a different style or brand.
The average man has a medium width of D. If a brand doesn’t specify a width, which most of them don’t, this is probably the width they use. Again, though, a brand’s definition of a D width varies, so watch out for the differences. A narrow width is a B, a wide width is E and an x-wide width is 3E.
If your foot falls between a B and a D, go with the larger width.
I see some places saying that if they’re lace-up shoes, like an Oxford Dress Shoe (Which they almost always should be, if they’re dress shoes!), you should not be able to tie the laces so tightly that the two edges of the shoe meet. I don’t adhere to this advice because some of my clients just have less meat than others on the tops/profile of their feet and when this happens, it’s not a problem. As long as the shoe fits everywhere else, I wouldn’t about this part.
If you have the width and length in check, this shouldn’t be an issue, but just in case: You want a little bit of space between your heel and the shoe, but not too much. My one finger test for sneakers is not applicable here. They should fit a little snugger than tennis shoes do in the heel, but should not be pressing against your heel as to be uncomfortable.
Lace up both shoes and take a short walk in them. There should be little to no slippage in the heel. If there is, they’ll create blisters on your heel and that’s not fun.
Also, since I hear this complaint a lot from guys – If there’s anything like a seam or stitching rubbing against your heel, don’t get those shoes. This is mostly typical in cheaper shoes. This area will never “break in”, so if something is rubbing against your heel when trying them on, it’ll never go away, so stay far away from them unless you like blisters on your heels!
See my Men’s Wardrobe Essentials – The Oxford Dress Shoe for my picks.
Well here’s my dirtly little secret – no matter their age or body shape – I fit their suits exactly the same. A well-fitting suit looks good on everybody. Can you guess how many times they’ve complained after we got them fitted in a suit?
The below items are everything I look at and adjust to ensure my clients look razor sharp in suits.
Note: The model used for these shots is around 6 feet tall. Just so you have some frame of reference.
The suit jacket length will dictate how “balanced” your upper body is to your lower body. Mess up the length of the jacket and the whole suit will look off. The jacket should end around mid-crotch if you’re under 5’9”. Mid to lower if you’re any taller than that.
The model’s jacket below is perfectly in the “mid-to-lower crotch” area. A tailor can shorten your jacket up to an inch without messing up it’s proportions, but they can never really let much out because there’s no fabric there. Overall, you generally want this part to already be perfect when you’re buying a suit, even off the rack.
You want the shoulder seams of the jacket to end at the end of your shoulders – where they start curving down to your arm, basically. You should see no divots or wrinkles in the shoulders anywhere. The shoulders should lay perfectly flat, with no divots or rumpling or pulling on the shoulders. If you have more rounded shoulders, the seam should still end in the same place, you would just need a little more padding in the shoulders to make them appear less rounded. If the shoulders are too big or small, a tailor will have a very hard time fixing this, and it would be very expensive – if it was even possible. So ensure these fit properly when buying a suit from anywhere, as well.
RealMenRealStyle has this awesome graphic showing the proper shoulder fit.
When you bend your wrist so your palms are facing the ground, the jacket sleeves should be about ¼” above the top of your hand. A lot of people recommend that it hits the top of your hand, but that’s BS – then none of your shirt sleeves will be showing, like in the picture below. This length allows for a little bit (¼”) of your shirt sleeve to peek through. If your sleeves are longer, a tailor can easily fix that. If they’re shorter by more than an 1.5″, ditch the jacket because there’s probably not enough fabric in the sleeves for your tailor to let out.
With the top button fastened (never the bottom button), the jacket should lightly hug your midsection, but not feel tight or constricting. The jacket shouldn’t be pulling at the button, creating an ugly “X”. The X mean’s it’s too tight. If it’s roomy around your stomach/waist area, you can (and should!) have a tailor take in the sides of the jacket so it fits properly. This is a very easy and common fix for a tailor to do. Remember: For tailoring purposes, it’s better to have a jacket that’s slightly too big in the body than too small.
For details about the items in this exact outfit, see here.
The collar should rest against your shirt collar, which in turn should rest against the back of your neck. All of these should touch lightly, without significant gaps in between. If there’s a gap, it’s too loose. If there’s bunching just under the back of the jacket collar, it’s too tight or the stance of the jacket is off.
They should be high, but not so high that they’re cutting into your armpit. The picture below shows where the armholes should be on your jacket. Notice it’s not cutting into his armpit? They should be large enough that you don’t notice them, but not so big that you have a few extra inches between your armpit and the bottom of the hole. The arms should be able to move somewhat independently of the jacket’s body during normal motion, but not excessively.
While I’m speaking about suits and motion, a lot of guys who are new to wearing suits usually complain that they should be able to move their arms more while wearing a suit. Let me tell you that a suit is not activewear, so don’t think you should be able to do everything you normally do while wearing a suit. It’s just not built for that purpose.
The jacket’s second button from the bottom (aka the top button) should lie just above your belly-button, never below. My rule of thumb is no more than an inch above and never, ever below. Otherwise it’ll throw off your body’s proportions and you’ll look really odd in the suit.
Suit pants should fit perfectly around your waist with no need for a belt to hold them up. They should hit around the high hipbone area, or even slightly higher. You do not wear suit pants at the same waist as jeans – which are usually designed to sit lower. Saggy dress pants is a big no no.
The seat, or butt area, should lightly hug your tokhis (Yiddish for butt – I just love the word) and not be saggy or super tight. If it feels like you’re going to split your pants, they’re way too tight. If you’ve got a bunch of extra fabric around the butt, they’re much too loose. A tailor can fix this, it won’t be easy or cheap, but if everything else on the pants fits, definitely get it done.
RealMenRealStyle has the perfect illustration of how the seat of your pants should fit
You want to be able to pinch around 1 inch of fabric on either side of your thigh. If it’s less than that, your pants are too tight. If it’s more, have your tailor slim the legs with a slight taper so that it gets narrower towards the ankle. This will look great on every body type/size.
Always default to having your suit pants hemmed to leave a slight break. It looks more polished and sharper than a full break and no break at the hem is a time & place kind of thing, and not generally for everyday wear. A slight break works for everyone.
If you’re not familiar with the different type of pant breaks, PrimerMag has some great images to help you understand:
A trick I do with all my clients is to have the tailor hem the pants so that it’s slightly longer at the back of the hem. That way, when you’re walking, you’ll show less sock and when standing still, it’ll lay nicer on the top and back of your shoe.
There are very few times, I’d argue almost never, when you’d cuff your suit pants. I’ve never cuffed suit pants for a single client because it’s not necessary, no matter their body type.
Check out my post about the Gray 2 Button Notch Lapel Suit for my favorite suits that’ll fit any budget and look amazing on every body type.