Believe it or not, there are some improved techniques involved in cleanly tucking in a shirt – three in fact. In this video, I outline all three and show you how to maximize your ability with them.
Don’t forget to check out this post’s sponsor KK&Jay and use the discount code “MS20” for 20% off your order.
Proper Length
Casual shirts are designed to fall somewhere between the bottom of the rise of the pants and the top of the waist band. This helps them avoid looking like night gowns when worn untucked.
However, a proper dress shirt should extend as long as possible without going into the legs of the pants. Dress shirts that are too short are most likely a size too small (and will reflect this in other areas as well). They should be sized up for the ideal fit.
Undershirt/Underwear Tuck
It will feel as weird as it looks, but it’s a worthwhile tip in a pinch. By tucking the undershirt into the waistband of a pair of underwear, the pull and friction the undershirt places on the dress shirt is minimized – preventing the dress shirt from being as likely to come untucked through regular daily motion.
Just don’t get caught wearing underwear this way if you want to keep any dignity.
Shirt Stays
I was hesitant about this option at first, but KK&Jay really sold me on them.
Shirt stays are designed to clip to the top of your socks and the bottom of your shirt. The elastic provides tension against both anchors and keeps your shirt tucked in.
The visual difference is huge and, as long as they’re worn properly, they’re not any less comfortable than going without.
For men who want the added detail of a superbly tucked in shirt, this is the way to go.
The primary element of being able to wear a suit with socks, is the cloth from which the suit is made.
While color and pattern can help make a finer suit look more appropriate without socks, the biggest factors are the material and the weave with which the suit is made.
Finely worsted wools – those that are traditionally associated with business and formal wear – should always be worn with socks.
The same goes for heavier winter-weight cloths like flannel and tweed – not because of a formal/casual contrast, but because these materials are worn in colder months – times when it’s inappropriate (and uncomfortable) to not have socks on.
Instead, focus on summer-weight cloths like linen and cotton and wools in thicker, more substantial weaves – such as hopsacks, basket weaves, and others.
When a suit has more texture, it appears more casual and is more appropriately worn without socks (or with the right kind of socks).
Shoe Style
Not all shoes will work without socks. Just like with suiting, the focus needs to be on the casual end of the spectrum, along with styles that are more appropriately worn in summer. No one wants to throw their bare feet into a pair of alpine boots.
Loafers, drivers, and derbies are all great options. As are nearly anything with a low cut that’s made in suede.
What should be avoided are heavier or more formal shoes like wingtips and captoes. Even when they’re casual enough, they have a more Rugged and outdoor association that makes them look off when worn without socks.
The one exception to the formality rule is a pair of double monk-straps. While they do dress up more than a pair of longwings, their design and versatility makes them entirely appropriate when worn sockless. Don’t hesitate to thrown them on with a pair of chinos or jeans either. They’ll help dress up a more casual look.
Proper Equipment
I’ve been spending my summers sockless for years now. And over that length of time, have tried many different approaches.
Some men can just slide their feet in or apply a little bit of baby powder to the insole of their shoes. Doesn’t work for me those as my feet get sweaty and the top will often get stuck to the inside of the shoes’ tongue – not fun or comfortable.
I’ve also tried to use washable cotton insoles. While these do help remove odor and prevent my feet from sticking to the insole, they do nothing about the top.
The best solution is to wear a no-show sock like these from BlackSocks. They provide all the benefits of wearing a dress sock, while still allowing you to embrace the sockless aesthetic.
I love two things about this brand compared to others I’ve used. First, they come in a few different sizes. My feet are on the smaller side and no-shows that are too big will often slip off the back of my heel. It’s uncomfortable and frustrating to deal with.
Second, the material they use is so small and light that they feel like a pair of dress shoes. Other brand will use thicker materials that can make my shoes feel too small.
Seriously, these from BlackSocks are the best I’ve used, and I’ve tried this a ton of different ways over the years.
The one caveat I’ll give is to avoid using these if you’re constantly slipping in and out of your shoes. The appearance they give off is a bit dainty and effeminate. If you’re in and out of your shoes often, you’re probably better off sticking with the insole route.
Conclusion
With these three factors dialed in, it’s easier, more stylish, and more comfortable to ditch your socks in the summer months.
It’s a style I recommend for guys who lean towards the Rakish Archetype. Embrace the fact that it’s a polarizing aesthetic and tends to be one people will either compliment or criticize you for.
Oh, and if you want a hookup on those no-show socks, I have one for you. Use the code MS20 for 20% off any order over $50 from now until September 1st.
Don’t know what I mean by Rakish? Well go check these out.
Want to know where you fall into the Three Masculine Style Archetypes?
Take this quick quiz and I’ll tell you. CLICK HERE
Want more?
Skipping the socks while wearing a suit isn’t something the average Joe does. When you pull it off, you’re telling a story with your style.
Learn the how men throughout time and across all cultures have use their clothing to communicate specific, masculine virtues and tell stories that lead to more success, happiness, and fulfillment.
Most men like to be consistent – both in how we define ourselves and how others perceive us. In fact, it’s such a strong desire that it often sends us into autopilot and is exploited by those who understand it.
In this video I talk about the effects that consistency has on most men’s relationship with their clothing, along with how you can use your appearance as a tool to help dampen the auto response of consistency and make sure you’re always in the driver’s seat.
One of the best ways to learn where you should and shouldn’t be consistent, is to understand the different Masculine Style Archetypes
Over the years I’ve gotten a lot of questions from readers about how to add elements of the Rugged and Rakish archetypes into their Refined, white-collar business wardrobes.
It’s a great question and shows just how intentionally you are dressing. As I’ve answered it for different readers, I’ve noticed three different ways to make a business uniform look a little more Rugged or Rakish
Most business attire operates under a moderate contrast. Dark trousers or suits, light shirts, and maybe a bit of a color pop in a tie. It’s not too muted, nor is it too vibrant and attention seeking.
A man who leans more towards the Rugged Archetype is better off toning down the contrast and working with colors that are analogous (close to each other on the color wheel).
Rather than a navy suit with a white shirt and green tie, he’s better off with a navy suit, darker blue shirt, and a tie that’s a deeper shade of blue or even a purple.
The opposite is true for Rakish men. They will want to up the contrast by choosing colors that are contrasting (opposite each other) or triadic (form a Y on the color wheel). Brighter shades, bolder patterns and more variations will all draw more attention and evoke more of the Rake.
From both the Rugged and Refined perspectives, increasing the amount of texture in a cloth helps make the style more personal.
A suit made from worsted wool is the industry standard for a reason. There is no visual or tactile variation and it appears professional and Refined. By changing the weave and the way in which the cloth is dyed – say with a birdseye or a nailhead – more visual texture can be introduced without affecting the way the cloth drapes or lies.
By taking the cloth to a further extreme – into realms of summer and winter fabrics and weights (think of linen, hopsack, flannel, and tweed) – even more texture is introduced and the garment strays further away from the Refined archetype.
The Rugged man will always want to lean a bit more textured. However, the Rakish man can use cloths that are finer or more textured. For him, it’s more about not being in the safe center than it is about the traditional association with a given texture.
Accessories
A man can stray too far from a work-appropriate wardrobe by diving headfirst into tweed suits or linen trousers. However, he can still inject some of his personality and his preferred Archetype by doing so with his accessories.
Selecting ties, pocket squares, and shoes that have more texture, play with the color variation, and have roots in other activities can all contribute a more Rugged or Rakish appearance.
Conclusion
There are myriad combinations that can come from understanding these three principles and the only way to truly learn how to apply them is through experimentation. Be willing to make mistakes and come up against the line – maybe even cross it a time or two.
Only from making these changes can a man truly understand the perfect, personal balance between the Three Archetypes in his own appearance.
Don’t know what I mean by Rugged, Refined, and Rakish? Well go check these out.
Want to know where you fall into the Three Masculine Style Archetypes?
Take this quick quiz and I’ll tell you. CLICK HERE
Want more?
Even when complying with a dress code, you’re still telling a story with your style.
Learn the how men throughout time and across all cultures have use their clothing to communicate specific, masculine virtues and tell stories that lead to more success, happiness, and fulfillment.
For years I wore what I assume most young men wear to sleep – a pair of old basketball shorts and maybe the occasional T-shirt.
But, as I got older, I decided I wanted to start wearing a little more. Maybe it had to do with sharing my bed with someone, maybe it was because I wanted to stop feeling like a teenager – whatever the reason, I decided to make a change.
And I haven’t turned back.
So today, I’m going to give you my three primary reasons to invest in a pair of real pajamas.
While it certainly isn’t the primary way in which a man should define himself, there is no reason for any man to not aspire to considering himself as well-dressed.
In order to do this, there needs to be real consistency in how he dresses. Otherwise it’s not inherently part of who he is. He’s just someone who occasionally dresses well.
His style isn’t an expression of who he actually is, just a costume he puts on and takes off when it suits him.
So, choosing to dress intentionally, in the environment in which it truly matters the least, is a form of behavior modification. It helps with a mindset shift in which the man who does so truly see himself as well-dressed.
It becomes easier and more comfortable to do so in situations in which it truly matters, because dressing well is ingrained as part of a man’s self-identity.
The Message it Conveys
When I was in high school, I distinctly remember spending the night at a friend’s house.
We were up way too late playing video games and were louder than we should have been. As a result, his dad came downstairs to tell us to shut up so he and his wife could get back to sleep.
As you can imagine in this kind of situation, the route my friend’s father chose was one of stern authority. We were outside the lines of acceptable behavior and he wanted us to know, and even feel a little intimidated to make sure we didn’t cross it again.
Problem was, he was an overweight guy and he came down in nothing but his underwear. Rather than scaring us into quieting down, we thought the whole thing was hilarious.
Both his credibility and authority were undermined by what he was wearing, and it watered down his message to the point where we didn’t take it nearly as seriously as we should have.
While it’s true that most people will never see us in our PJ’s, the times in which they do are often when a man is at his most exposed and vulnerable. Think of an emergency evacuation because of a fire alarm or a burglar breaking into a home.
In these situations, a man’s clothing should be the furthest thing from his mind. But that doesn’t mean it can’t help or hinder his ability to perform more necessary duties.
A pair of pajamas may not be as good as a set of armor, but it goes a long way in helping to curtail any perceived vulnerability or weakness in times when that perception can be crucial.
Comfort
I know I never really talk about comfort, and I still stand by that for the majority of a man’s wardrobe.
But sleepwear is entirely different. If what he’s wearing isn’t comfortable, it can affect the quality of his sleep and have a major impact on his effectiveness when he’s awake.
By purchasing a pair of quality pajamas – those made from materials designed to increase airflow and breathability, and which are cut in a way to maximize comfort – sleep quality can improve.
Yes a real pair of pajamas can lead to better sleep than a pair of sweatpants and an XL t-shirt.
How to Wear Them
Just because a pair of pajamas is worth wearing, doesn’t mean that they all need to look the same. In order to illustrate this point, I’m going to use three different iterations.
The Dude
This will be the easiest transition and be the most common.
No one will be winning any style awards for an ensemble like this, but the materials are cool and breathable, and the coverage and style are enough to prevent embarrassment.
The Dad
This is my personal go-to throughout the majority of the year. It’s the same as above, but there’s a night robe thrown in.
Most of the time I’m sleeping in the Dude setup, but both before I go to bed and after I wake up, I’ll have a night robe on.
It’s the ideal image for me to present to my family. There’s a bit more intentionality along with a lot more visual power than there would be otherwise. I’m not embarrassed to go out and grab the mail in this getup.
The Dignitary
When purchasing a pair of bottoms, it’s better to buy a set as a whole. While it’s not always necessary to wear the full pajama kit, there are benefits to doing so in the right environment.
I choose to wear the shirt in place of a T during the winter months as it allows for more warmth.
However, the majority of the time I’m in this ensemble is when I find myself spending the night with company.
We take the occasional trip with family or friends and this can often lead to shared mornings before everyone has had the chance to get ready.
Both the Dude and the Dad are a little to “at home” for these environments. There’s something about that top layer, the message it conveys, its history and tradition, that end up adding more respectability and authority to the man wearing it.
So whenever I know I’ll be in PJ’s with someone beyond my immediate family, this is my default.
Conclusion
Whichever you choose, just make sure you take the time to find the right pair. It’s worth investing the little bit of effort and money to find the right set.
To that end, I’ve worked out a deal for you guys. Other than the night robe, everything that’s been shown in this post comes from Tani, and I have a coupon for you.
Go check out there incredible stuff (I’ve really never owned better pajamas) and when you’re ready to pick them up for yourself, use the code “style25” It will give you 25% off your entire order and help get you feeling, looking, and sleeping better at night.
