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.
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.
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.
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.
Henley shirts are one of the few items that, to me, don’t really have a specific season they’re best worn in because there’s so many different versions for men. Other shirts, like T-Shirts, Polo Shirts and DressShirts don’t really have this problem since they’re pretty standard across the board no matter the season.
I love henleys, because they look sexy and masculine, especially when the top 1 or 2 buttons are undone to draw the eyes to your chest and shoulders to show off your physique in a flattering way. Hence, the image below.
BUT, and this is a big mistake I see a lot of men making – they’re not for every everyone. More on that shortly.
Let’s get into what to look for in your henleys based on the time of year.
Fabric
Generally, henleys will be made out of cotton, so there’s really not much choice outside of that, but you still need to consider fabric weights depending on the time of year. The main thing to know is that lighter weights should be worn in warmer months or in warmer climates and thicker, heavier fabrics in cooler months or climates. You can get them in everything from a lightweight summer weave, where it feels like a t-shirt, to thicker, quilted versions which will keep you warm during the cooler months.
You don’t have to worry too much when buying them because, based on the time of year, the brands will carry the appropriate weights. But I still want you to be aware of it just in case.
Fit
Like all your clothing, including henleys, they should have a trim fit throughout the body and arms – no matter your body type. You never want it too loose anywhere because that’s when you’ll look sloppy and not put together. You shouldn’t be able to pinch more than 1-2 inches of fabric on one side of your stomach and no more than an inch around the bicep.
The image below highlights the proper fit around the torso and sleeves.
I mentioned earlier that henleys aren’t for everyone, so let’s get into that right now since we’re talking about fit.
For Thin Gentleman
If you’re a thin guy, no matter your height, if you want to wear a henley, you absolutely need to nail the fit, especially if you’re going to wear a long sleeve version. If the fit is too loose, it’ll make you look thinner and more frail than you are – not good!
I only like long sleeve henleys on thinner men if they’re layered underneath a jacket, like the below right image. When worn on their own, it really spotlights and elongates your thinner torso, like image on the left. So if you’re a thinner guy and want to wear a henley on its own, then wear a short sleeve version since it’ll look similar to your t-shirts.
Bigger Gentleman
If you’re a rotund gentleman (aka you’re not in the greatest shape and have a belly), you cannot wear a henley shirt, period. Allow me to show you why and explain. See exhibit A:
Because of the button placket on the front, coupled with the lack of a collar, a henley will shine a massive spotlight on your bigger neck and torso. This is when a polo shirt is perfect and should be used instead, because a polo shirt’s collar will visually keep your torso balanced and in proportion, so your top half doesn’t look so big compared to your bottom half. The image below of James Corden shows a guy with the exact same body type as the image above, but in a polo shirt. Talk about a night and day difference…
Best Ways To Wear A Henley Shirt
Think of your short sleeve henley as a t-shirt, they’re interchangeable in the same outfits, so that means they can be worn on their own or underneath a jacket.
For a long sleeve, you would normally wear these during the cooler months as a layering piece, so I styled Dorian in a long sleeve henley shirt underneath a bomber jacket, dark wash jeans, and sneakers.
During the warmer months you can wear them with the sleeves pushed up. As I mentioned in one of my other videos, women LOVE to see sleeves rolled/pushed up around your forearms.
My Favorite Henley Shirts
Here are some great short sleeve and long sleeve (lightweight and heavyweight) henley options that I love.
Last Sunday I was getting a client ready for the Oscars, and a friend of his was wearing this incredible lightweight wool jacket that I knew I had to share with you. It’s been quite awhile since a jacket got me this excited.
There’s several reasons why I love this jacket for Spring and Summer, or year-round if you live in a warmer climate: lightweight wool and cotton fabric, incredible construction, texture and color, and its so damn stylish. Normally, I’m not a fan of pockets on the front of a jacket for all body types, as they can add bulk and throw off your proportions if you’re a thinner guy, but, as you’ll see in the video above, these pockets blended in so seamlessly that it isn’t an issue at all.
Wear it with a t-shirt, jeans, and sneakers or dress it up with a collared shirt, wool trousers, and dress shoes – it will go with most casual and dressy casual outfits. Yep, this jacket is that good.
Jacket
I went into the store and had my friend Michael, who’s average height but a broad build, and Dorian, who’s 6’3″ and slim, try the jacket on and they both looked great in it. See the video above to see what I’m talking about. Also, Dorian ended up picking up the blazer version of the Chore jacket for himself.
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
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.
This article & video is part of the Celebrity Style Inspiration Series, where Antonio Centeno from RealMenRealStyle.com and I pick out great outfits from movies and tv shows and demonstrate how to recreate and incorporate them into your wardrobe.
As Antonio and I discussed in our other video about Chiwetel Ejiofor’s outfits to emulate, I love how unexpected this one was because who would watch a space movie and think they’d have amazing outfits in it? I thought Chiwetel Ejiofor’s style in the film hit the perfect sweet spot between dressy and casual that’ll be great for any man, regardless of his age or body type. I also wanted to include this one, because I’ve gotten a lot of questions from readers and viewers about how to wear shades of the same color. So I felt this was the perfect opportunity to show how it works.
Here’s the full outfit I’m going to recreate. I wish the full length images were a little brighter, but these were the best shots I could find. Also, they never fully show his shoes, so I’m having to guess a little bit on this one.
The Cardigan & Shirt
Chiwetel is wearing a blue knit shawl collar cardigan with an oxford button down dress shirt. I put my model in a sweater by Rag & Bone and a Brooks Brothers Oxford shirt since they’re just so damn good. Check the outfit details at the bottom of this page for images and links.
Funny enough, I created a similar look for my t-shirt story.
Pants, Shoes & Accessories
As for the pants, here’s wearing olive chino pants – which are just fine. But I don’t think olive is such a universal color and it’ll be hard to put them into other outfits. Since I’m a huge fan of dark wash jeans, especially for creating a more monochromatic look like I did with my model, I went with those instead. I also did this because it allows me to use some of my favorite shoes ever. Please follow my chino pants fit guide or my jeans fit guide so they’ll look amazing on you, regardless of your body type.
Like I mentioned in the intro, his shoes are never shown with this outfit, but to me this was an easy choice to go with some beautiful brown chukka boots. Blues like this are begging for a nice rich brown leather shoe and accessories, so I had to go with them.
Check my outfit details below to see the chukkas and accessories I’d pair with this outfit.
My Version of this outfit
Here’s my slightly modified version of Chiwetel Ejiofor’s outfit from The Martian. I hope you enjoy it!
Rag & Bone Avery Shawl Cardigan
Brooks Brothers Non-Iron Milano Fit Button Down Collar Shirt
This article & video is part of the Celebrity Style Inspiration Series, where Antonio Centeno from RealMenRealStyle.com and I pick out great outfits from movies and tv shows and demonstrate how to recreate and incorporate them into your wardrobe.
As Antonio and I discussed in our other video about James Bond outfits to emulate, I really love the casual outfits Daniel Craig wears, so I wanted to recreate this one from Quantum of Solace, because it’s clean, simple and looks amazing on every guy, regardless of his age or body type.
Unlike the other video, where I switched out some items for more practical options, this one is already very practical, aside from the shoes. But we’ll get into that in a moment.
Here’s the full outfit I’m going to recreate. Apologies for the blurriness, but they don’t show this outfit for very long and the full-length shot is focused on a woman in a bikini to the right of Bond.
The Cardigan & Shirt
Daniel Craig is wearing a black shawl collar cardigan which is so warm and comfy. I certainly wouldn’t advise wearing this during summer time, but for any other time of year, there’s nothing better than a shawl collar cardigan. I put my model in one from Todd Snyder, but check the outfit details at the bottom of this page, because Todd Snyder no longer makes that cardigan, but I included a very worthy substitute.
Now, with the shirt, you can either go with an Oxford button down, like I have my model wearing below or you can go with a semi-spread collar dress shirt. if you wanted to dress it down a bit more, you can go with a white v-neck t-shirt, like Daniel Craig also wore in Casino Royale.
In the full length image at the top of the page, you’ll see bond is wearing brown suede chukka boots, which as I mentioned in the companion video to this one on Antonio’s Real Men Real Style channel, I’m not the biggest fan because they get gross and dirty quite quickly. So instead, I’d go for something like brown oxford dress shoes. That way, you’ll keep the same general profile as the original outfit and you hopefully already have these in your closet, so it’s a perfect way to incorporate them into a more casual outfit. I find a lot of men have a problem with mixing their dress shoes into more casual outfits and this is a perfect example of when it’s appropriate to add them in.
The final piece of the puzzle is the sunglasses. Daniel Craig is wearing aviators by Tom Ford in the film, but whether you should be wearing those or another style is dependent on your face shape. Since my model has a more oval face shape, I went with squared Tom Ford wayfarer-style sunglasses instead.
My Version of this outfit
I also wanted to mix a more budget-friendly piece, like the chino pants, with less budget-friendly items, because for some reason, a lot of men think that if they’re wearing an expensive item, everything else has to be equally expensive or it just won’t look right. Well, hopefully you see that this couldn’t be further from the truth.
Rag & Bone Avery Shawl Cardigan
Brooks Brothers Red Fleece White Solid Oxford Sport Shirt
The Navy Blazer or Sport Coat or Sports Jacket, whatever you want to call it (we’ll go with Blazer from here on out), is an essential because it’s the very definition of business or dressy casual. It pairs incredibly well with dark wash jeans, oxford or semi-spread collar dress shirts, Oxford dress shoes and almost any other mix of dressy or casual wear in your Essential Wardrobe.
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.
Blazer vs Sport Coat
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.
Blazer vs Suit Jacket
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.
How To Tell A Blazer From A Suit Jacket
Here’s my patented 4-Step process to tell if a jacket is a Blazer or a Suit Jacket:
If the buttons on the sleeves and torso are metal of any kind – that’s a Blazer.
If it has matching pants – that’s a Suit Jacket.
If the jacket is thinner or more delicate feeling – that’s a Suit Jacket.
If it’s heavier, thicker or sturdier feeling – that’s a Blazer.
Fabric
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.
The Best Colors for A Blazer or Sport Coat
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.
Vent Type
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.
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.
Brooks Brothers Charcoal Milano Fit Herringbone Blazer
Brooks Brothers Navy Fitzgerald Fit Two-Button Blazer
Burberry Gray Slim Fit Travel Tailoring Jacket
Emporio Armani Navy Jacket in Textured Wool
Ralph Lauren Purple Label Navy Nigel Wool-Cashmere Blazer
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.
