It’s officially polo shirt weather but you’re probably still needing a layer here and there. In this week’s edition of 2 Minute Tuesday we’re going over a few rules when it comes to layering a sweater with a polo shirt. Here’s how to do it right.
Layering Tips
Skip the polo under a sweater Wear a button up dress shirt or an oxford underneath a sweater, a polo shirt shouldn’t be worn over a sweater as the collar of the shirt doesn’t have enough structure. This goes for all types of sweaters – crewneck, v-neck, and shawl collar sweaters.
Wear a blazer, bomber, or Harrington instead If you do want to add a layer over a polo shirt, try a bomber jacket or Harrington jacket instead, they are better suited to the style of a polo shirt. A blazer can be worn over a polo but we recommend sticking to a polo that has a neat, structured collar and stays put underneath your jacket.
We’ve talked about polo shirts in the past, and for good reason, they’re one of my favorite elevated casual items, especially for the Spring and Summer months. Here are our style tips and picks for the best men’s polos for 2018! Don’t forget to check out my picks below and for more info on fit, read our polo shirt fit guide.
There’s only a few weeks of Winter left, so pretty soon we’re all going to have to start thinking about transitioning to our Spring wardrobe. So in addition to your year-round Men’s Essential staples that are already in your closet, Jordan O’Brien from The Gentlemans Cove and I each came up with a list of 10 Spring Essentials that every man should own.
My Top 10 Men’s Spring Essentials
1. Lightweight, Spring Suit
Whether you go with a linen, cotton, seersucker, or lightweight wool suit, these options will make a statement and keep you cool throughout the Spring and Summer months.
These lightweight blazers are perfect for casual Fridays at work or heading to lunch or dinner with friends. They’re a great way to insert a stylish statement while keeping cool. Linen will wrinkle a bit, but that’s part of its character so embrace it.
I love gingham shirts for the Spring because they can be worn dressed up with a suit or blazer or dressed down on their own or underneath a sweater. I included some great lavender, navy, and light grey gingham options below.
There’s no other brand that I love more than The Tie Bar. The quality, construction, and color/pattern choice can’t be beat by any other brand. Like I’ve always said, they’re not paying me to say this.
Polo shirts instantly make an outfit look more put together and Spring is the perfect time to start wearing them. I like John Varvatos, but be careful if you’re not in shape or have erect nipples because their silkier shirts will highlight these areas. The fit on Theory and Fred Perry polos is excellent and H&M is my go-to when I’m more price-conscious. You’ll need to replace those roughly every 8 weeks though due to fading.
Not only do short sleeve button-up shirts look stylish, but every man (regardless of age or body type) can wear these. There’s currently so many great options from J.Crew and come March/April, Topman will have an equally great selection.
I’ve maintained in some of my other videos and articles that you should save your suede for Spring. Well, it’s time to break out those items. I love the options below – you can choose from navy, light grey, and brown suede jackets. The A.P.C. jacket is a BIFL piece and will never go out of style.
Finally we’re entering ankle season, which means penny loafers can finally be worn. I love Ferragamo’s loafers (I got a pair for my fiance Dorian 2 or 3 years ago) and they’re totally worth the price because they definitely hold up and still look great after years and years of wear.
Suede monkstraps, whether you get a dark brown, grey, or navy pair, can just take an outfit to another level. It’s such a stylish touch to any outfit and can be worn with a suit, chinos, or jeans. Make sure to Scotch Guard them before you wear them for the first time – always gotta protect your suede items!
Chinos should only be worn in Spring, Summer, and early Fall and that’s it. They’re a great alternative for those days when you don’t feel like wearing jeans and when you want to just feel cool and comfortable.
These as well as other great alternatives were included in my Summer Essentials E-Book. A lot of Jordan’s picks I actually included in that e-book so be sure to check it out if you haven’t already 🙂
Linen, as well as the other lightweight fabrics I also included in my list, is very breathable and will keep you cool during the warmer months. Here are some of my favorite items currently available.
Whether you need some extra sun protection or want to look stylish while staying cool, straw hats are super breathable and lightweight. Every year I get J.Crew’s panama hat, but it only lasts the season before it starts to fall apart. I’m currently eyeing Loro Piana, Brooks Brothers and Stetson’s hats because I know I can count on the quality and construction.
I like long sleeve henleys when they’re worn as a layering piece, so underneath a casual button down shirt paired with some dark wash jeans and boots or sneakers. If you’re a slim or wider gentleman, I highly advise against wearing henleys on their own because they emphasize your body size even more (and not in a good way).
If you’re new to wearing denim jackets, I suggest going with a black or dark grey version because it’ll be a lot easier to wear, especially if you wear jeans a lot because you don’t want to look like you’re wearing a Canadian tuxedo.
I’ve already talked pretty extensively about ties and pocket squares in my Men’s Essential Accessories series, so if you haven’t sen those articles/videos and don’t know the size of ties you should be wearing or the best ways to fold your pocket squares, check them out. The wool ties & pocket squares I’ll be discussing below are essential for the Fall and Winter seasons because they will compliment the items in your Fall/Winter Wardrobe nicely.
Material
For your ties and pocket squares during this season, you need to go all in with wool. There’s also technically cashmere, but there’s not a lot of them being made and I find them to be obscenely expensive when a wool tie looks just as good.
The reason you go all in on wool is because you want your accessories to compliment the fabric weights of the items you’ll be wearing during the various seasons, so if you were wearing silk or linen ties, which are for Spring and Summer, with your heavier wool suits or sport coats, it would look really off.
Colors
As I mentioned in the Series intro, this is the time of year to wear some nice, rich colors, like:
greens
shades of blues
burnt oranges
grays
burgundy
browns
Patterns
As far as patterns, it’s also the best time of year to wear plaids, paisleys and polka dots because they’re visually heavy and pair so well with your Fall and Winter wardrobe.
The one area that I see men really have an issue, though, is with matching these patterns and colors together with their outfits or other accessories.
A good rule of thumb is:
If your tie is a bolder pattern, like a paisley or plaid, then you want your pocket square to be more subtle or as close to a solid color as possible. It doesn’t have to be a solid, but when in doubt, go for a solid one. This ensures you don’t have too many patterns clashing. (See the video above and outfit images below for examples)
And the inverse is true for a patterned pocket square – go for a solid or very subtle patterned tie.
This helps balance these items out so you don’t look like a goofball.
The ties from Tom Ford, Alexander Olch, and Thom Sweeney are pricey, but you’re paying for a high quality, luxurious accessory that’s timeless. If you’re going to shell out this amount of money for a tie, then you want to make sure it’s easy to wear and it’ll never go out of style.
For fun patterned ties that are also easy on the wallet, I’m a huge fan of The Tie Bar (and no, they’re not paying me to say this). For great textured wool ties in solid colors, I love J.Crew. They also made a charcoal chalk stripe tie that is really easy to wear with your existing wardrobe.
Brunello Cucinelli makes probably the best – in terms of color, pattern, and quality – pocket squares out there, in my opinion. The Hugo Boss and Alexander Olch pocket square and rounds are all the perfect shade of grey so they’ll pop really nicely from your darker suits or sportcoats.
The striped J.Crew pocket square will go with pretty much every Fall suit/sportcoat you have. For some great patterened options at an incredible price point, I love the double sided ones by The Tie Bar.
The best jackets for the Fall (and Winter if you live in a climate like Southern California) are bombers, trucker & flight jackets, as well as utility (aka M65 aka Safari aka Field) jackets. Now, which one you should wear depends on your body type and how you’ll be wearing it. But I’ll get into that shortly.
The goal with your jacket, just like everything else in your wardrobe, should be to create a sharp, polished look and not draw attention away from the rest of your outfit. With that being said, your jacket is a great place to insert those Fall colors ( I specifically like dark green, camel, navy or black for these jackets) I was talking about in the series intro.
I love a good wool or suede trucker or flight jacket for the Fall. I’m lumping these together because they look very similar. A trucker is basically a denim jacket but in a different material. I’m not going to discuss denim jackets because those are really a spring/summer item because they’re not very warm.
A trucker usually has buttons on the front and a flight jacket has a zipper front. You want to make sure your jacket stops at hip level, like a bomber would, and is fitted through your shoulders and torso. There are a ton of trucker jackets out there that have shearling or fur collars, which I really love, but I’d recommend choosing a jacket where you have the option of removing the collar, that way, you can get two different looks out of one jacket.
If you’re a broader guy, I wouldn’t recommend this jacket because the combination of the collar and shorter length of the jacket will make you look really top heavy. With your body type, whenever you have a jacket that stops at hip level, you want to make sure it’s as streamlined as possible, like a bomber.
Speaking of bomber jackets, I consider them the utility infielder of the jacket world. I use them all the time with clients because they look great on every man, regardless of his body type. They break up your body at the waist nicely, keeping everything proportional.
If you’re a guy with a larger midsection, the one thing to watch out for with bomber jackets is zipping it up. If you do that, you just created a large swath of fabric that’ll actually accentuate your mid-section. So if you’ve got a bit of a belly or are just a bigger guy, do not zip up your bomber jacket, ever. And I’m not joking about that, either.
The last type of jacket I love for Fall and Winter is a utility jacket, aka Safari, Field, or an M65 jacket.
This jacket differs from my other favorites because if it fits well, it’ll hit somewhere between mid to lower crotch – so it’s a great option if you want a longer jacket. But please, nothing longer or shorter than that, otherwise it’ll throw off the proportions of your body. I really like this style for heavier men, almost more than a bomber or trucker style because the slightly longer jacket length and pockets on the front break up your broader torso and will make you look smaller.
And if you’re a thinner guy – just beware of this style of jacket that has a hood in the collar because it will look too bulky/heavy around your thinner frame, especially the neck area, and will actually make you look skinnier. Instead, you need your jacket to have a standing collar or at least a collar that’s free from any puffiness.
Regardless of your body type, this type of jacket needs to be very fitted throughout so it doesn’t look like you’re swimming in a bunch of pockets and fabric. This is important because it can make a thin guy look skinnier and a broader gentlemen look even heavier than he is.
I like suede or leather for Fall/Winter because it’s visually heavier, but just be careful about wearing suede in wet or snowy weather. But if you don’t want leather or suede, you can use a cotton or wool bomber or trucker, as well.
For utility jackets, anything but leather goes. They look a little too 70’s pornstar-ish to me.
A plain, short sleeved t-shirt is an essential because they’re super comfortable, timeless, and everyone wears them. Now whether you need a crew neck or v-neck t-shirt is dependent on a few factors that I’ll get into later on in this article.
If you’re like most of my clients, you’re probably wearing a t-shirt or polo shirt most of the time, so let’s make sure you look amazing in them. Before we get into that, though, I have a few bones to pick with men in regards to their t-shirts. They completely crap the bed in a few ways:
Their shirts are full of logos.
They don’t fit properly.
The fabric is too thin, shiny, or worn out.
A horrible combination of the above.
Types of T-Shirts For Men
A t-shirt is defined as:
A lightweight shirt without buttons, with short sleeves and no collar. Often made of cotton and frequently bears a picture or slogan.
Before we get into the finer points of t-shirts, let’s talk about the two different types, first. Before I started in the fashion industry, I didn’t know that there were only really two types of t-shirts. So let’s quickly get this out of the way.
Crew Neck
These t-shirts have round collars that fit closely to the neck like the image above. You probably have these in your closet right now. They are great base items for layering or worn on their own. They work on most body types. See the below section about fit for more details.
V-Neck
If your powers of deduction are strong, you’ll already know that the v-neck t-shirt is named as such because the neck is in the shape of a “v”. They also work on most body types. See the below section about fit for more details.
Long Sleeves
Long-sleeved shirts are not technially t-shirts. I put this here, because when I was first starting out, I swore that long-sleeved shirts, like Henleys, were also t-shirts. But, they’re not. Also, in my professional opinion you shouldn’t really own any long sleeve shirts. Henleys would be the only exception, but they only look good on certain body types. I’ll do an article about Henley shirts at a later time. But I don’t consider them a wardrobe essential.
I discussed my hatred of logos in my polo shirt article. And it definitely applies to t-shirts. Maybe more-so.
No self-respecting man should ever wear t-shirts with logos plastered all over them. We have enough billboards and advertisements in our lives, don’t turn your body into another one. Sports teams and concert/band tees are fine if worn to an event where it’s appropriate. But the worst is when I see guys wearing “designer” t-shirts. It just screams sucker, amateur and douche. Just don’t do it. If you own any of these, either throw them out right now or
How T-Shirts Should Fit
See the T-Shirt Fit Guide for details. But I’ll quickly mention here, too, that no matter your age or body type, a t-shirt (any shirt, for that matter) should have a trim fit and lightly hug your body.
That doesn’t mean it should be skin tight, but it also doesn’t mean it should be baggy, either. A lot of my clients with larger builds tend to think that their shirts need to be baggy to hide their imperfections, but it actually works counter to that. It’ll highlight your imperfections if you attempt to hide them under larger swaths of fabric. And if you’re thinner, a larger shirt won’t add any bulk to your frame, it’ll just make you look even skinnier.
Fabric Choice
I can’t tell you how many nipples and belly buttons I see walking around town because guys are wearing undershirts or flimsy shirts with really thin or delicate fabrics as regular t-shirts.
Too Thin
I see a lot of guys wearing what looks like white undershirts because the fabric is so thin. I’ve honestly been searching for months for good white shirts that don’t show skin through. See my recommendations below. Thin shirts/undershirts are not the same as regular t-shirts. Undershirts, true to their name, should only be worn underneath another shirt – usually an Oxford Button Down Dress Shirt or a Semi-Spread Collar Dress Shirt. They’re thin and soft because they’re purpose-built to go underneath something else.
Silky or Shiny appearance
The quickest way to look like a creepy uncle is to wear a shiny or silky t-shirt. You should only wear cotton and matte (not shiny) t-shirts. Nothing else.
Distressed or Worn out
Your t-shirts shouldn’t look like the garment equivalent of those terrible worn-out baseball caps. A t-shirt should look clean, comfortable and relatively new. Once they’ve got holes or they’re faded, even a little bit, they need to be replaced. Such is the nature of being a well-dressed gentleman. There’s nothing worse than old, stretched-out, or faded looking shirts, unless you’re deliberately going for that look.
You’ll get more usage out of your t-shirts if you wash in cold water and hang dry them. But once they’re stretched out or faded, it’s time to donate and replace them.
The Best T-Shirts For Men
Choosing the best t-shirts comes down to your body type, preference and the colors. I’ll reiterate again, because my older clients like to give me this excuse before they see the light: AGE DOESN’T FACTOR INTO WHAT SHIRTS YOU SHOULD GET – AT ALL.
Should I have V-Necks or Crew Necks?
Between the two, I would say it all depends on your preference. Some of my clients are adamant about their love or hate for one or the other. But if you don’t have a preference, I’d suggest getting one set of each. That way, you have the option to switch it up.
As for which ones you should get, there’s 3 points to consider:
If you have a longer neck, go with crew necks. A v-neck would visually lengthen your neck and make it look longer. Unless you can find shorter v-necks with a shorter “v” like the white shirt on my model below.
If you have a shorter neck, go with v-necks. It’ll make your neck appear a little longer.
If your neck is average, the t-shirt world is your oyster and you can have whatever you want!
What colors should I have?
Every man should have these colors to start since they’ll go with everything else in your Essential Wardrobe.
White
Heather gray
Navy
Black
As for how many of each you should have, I suggest getting at least 2 of each, that way you can easily get through a week without needing to do laundry.
Best T-Shirts For Men
Designer Options
The fabrics of these options are really amazing and super comfortable. The James Perse ones are a personal favorite and I use them on a lot of my clients. I wish I could make all my clothes out of some of these materials. See my note in the section below, before making your decision. All of these shirts come in the colors I recommended above.
I’d probably default to these options over the designer ones because I find very minute differences between them. The biggest factors would be fit and slightly better fabrics. I don’t find the added costs are worth what you get in return, especially because t-shirts will need to be replaced much quicker than other items in your wardrobe. All of these shirts come in the colors I recommended above. I especially love the RibbedTee shirts and the American Apparel Summer Shirts.
All Saints White Figure Crew T-Shirt
Armani Exchange Grey Pima V-Neck Tee
Armani Exchange Black Pima Crew Tee
American Apparel Grey Tri-Blend Short Sleeve Track Shirt
American Apparel White Sheer Jersey Short Sleeve Summer T-Shirt
RibbedTee White Rex Cotton Modal Tee V-Neck 1-Pack
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.
Q: How do I dress in a more “mature” style that makes me look my age?
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.
$198 – 
$480 – 
$1,455- 
$760 – 
$698 – 
$575 –
$165 – 
$2,000 – 
$90 – 
$150 – 
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