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A guide to help the average man... look less average

Filtering by Category: Confidence

Looking good in different types of clothing

Mark Kwak

When in doubt, I advocate many folks to "grow up" their look. Wear button up shirts instead of T-shirts. Shed the flip flops in favor of a nice pair of wingtips. Put on a nice wristwatch. Now, some people are fortunate enough to be in situations where they simply do not need to wear these types of clothing. Be it people who are constantly active and on the run, or perhaps artistic types that are encouraged to dress a bit more eclectic than the average "well-dressed" guy.

To me, these types of occupations or lifestyles are no excuse not to wear clothing that looks good, feels good, and fits well. Just because you're not sporting a blazer and tie doesn't mean you can't look awesome. Let me try to show you some great looks even when you don't have just a normal office job.

1. The active, sports man

Zip up hoodie, dri-fit T-shirt, fitted track pants, Nike frees.

I think that activewear can look great these days. All the dry fit, compression based clothing helps keep clothing slim,

2. The eclectic type

Whatever clothing you want.

There are two people that I think dress well, albeit a bit more eclectic than I would prefer. Pharrell and Andre 3000. Take a page from their book if you're in the mood. Sometimes when you have a very confident sense of personal style, you can still look quite good in even the most ridiculous or outlandish clothing out there. Just make sure it fits well, and you wear the outfit with the utmost confidence.

3. The rugged outdoorsman

Barbour jacket, chunky wool sweater, denim or cords, rugged boots.

Just because you're out in the wilderness doesn't mean you can't look great. In fact, so much of menswear today is about sporting that rugged outdoorsman look, even if going just to the office.

4. The lazy at home type

T shirt, sweat pants, beanie, perhaps a hoodie or sweatshirt, New Balance.

I don't know if you've been following menswear magazines these days, but T-shirts, sweatpants and sweatshirts are more prevalent than I've ever seen. You know, back in the Mad Men era, when men wanted to just lounge around the house, they would dress down into a sport coat. Boy those days are gone. Instead, feel free to wear a nicely fitting sweatpant or sweatshirt to look good.

Whatever the look, there's a way to make it look good. You don't always have to be in a suit and tie, right?

Do I care how you dress around me?

Mark Kwak

When my friends find out that I write this blog, I usually get a couple very similar responses, one of them being, "oh shoot, this means I probably should dress better when I'm around you."

This cracks me up, and here's why.

People who have tons of information about a particular subject can often engage in some sort of snobbery around that subject. Think wine connoisseurs or coffee enthusiasts. When people find out that this person has this wealth of knowledge, they might get self conscious about their own knowledge on the subject, and start to worry if they're being judged by their ignorance.

I get it, I'm sometimes self conscious about enjoying a crappy wine if I'm with my wine-freak friends. However, unlike a lot of subjects, here are a couple great things about style:

1. There is no true right or wrong. Yeah sure, there are rules you can adhere to, like not wearing the same color denim on your jacket as your pants, or having your suit pants end at a half break instead of dragging on the floor, etc. However, people break these rules all the time, and this includes people who are in the know about fashion inside out. I see well-dressed folk wearing oversized this, or baggy that, on purpose! It's all subjective.

2. The more confidence you have, the more your outfit starts to fade away. Yes, I believe style is important and that's why I continue to write simpler man. However, the one major thing people forget is that style is largely about showcasing you, not just your clothing. You do you, man. As long as you do that, no one will even notice that you're wearing a jacket that doesn't complement your denim very well.

Either way, when it comes to me personally, I have zero expectation of my friends to dress better around me. In fact, when certain friends have a lot to learn about style, I actually get excited, and want to help them if they have any desire to learn more. Knowing that I have information that can potentially help these folks makes me happy.

The only thing that may tick me off is someone's insistence on caring less. People who refuse to learn anything more about dressing better, simply because they think they know it all already, or are too lazy to ever care. Don't be one of those people please.

Anyhow, if you ever come across style bloggers or fashion enthusiasts in the city, don't ever feel self conscious about your outfit. You dressed that way because it's probably a part of who you are, and most people would rather you be more genuine than staged. Doesn't mean don't continue to learn, but just be real. Plus, I may just be wearing some ill-fitting sweats and a nasty T-shirt myself, don't judge.

Doesn't take as much as you think

Mark Kwak

I'll be honest. In the world of menswear, things can get a little pretentious and overtly critical. As invaluable as resources like MFA on Reddit and Styleforum are for learning more about clothing, it can get a little intimidating to put yourself out there due to the likelihood of criticism and curses that may come your way for not quite standing up to their standards.

A seemingly normal getup in the #menswear world might consist of...

*inhale* fancy patterned tweed sport coats, artisanal pocket squares, handmade silk knit ties, rare colored shell cordovan oxfords, matching shell cordovan belts, perfectly tailored wool flannel trousers with a 2 inch cuff, astronomically expensive Swiss-made watches, European designer dress shirts with mother of pearl buttons, argyle wool socks, cashmere silk blend scarves, and locally sewn fedoras to top it all off. *exhale*

Well, for rest of you who are merely on a quest to look better than you currently do, let me remind you that it doesn't really take all of... that. As I've told you many times before, as long as your clothing is simple and fits well, you can look quite terrific. To remind you of some of these quite basic tips:

Try to mostly stick with basic colors. White, grey, navy, black, and blue.

Keep it simple. Plain T shirts, slim solid-colored dress shirts, straight leg denim, etc. The more simplicity, the easier it will be to mix and match.

Make sure the fit is as good as you can get it. This one is the hardest of the bunch because most guys are unfamiliar with what a good fit actually looks like. Just make sure there is very little extra fabric around, that lengths of sleeves, pants, etc. are paid attention to, and that you feel good when looking at yourself in the mirror while wearing your new clothes.

Find an honest friend. Appoint one of your friends who dresses well to judge your outfits every now and again. They should be able to point out what works and what doesn't. Don't be afraid of criticism as that's the only way you'll get any better!

Follow those quite simple tasks above and you should be able to improve the way you look substantially. Don't worry about the handmade knit ties just yet, you'll eventually get there.


Making style mistakes

Mark Kwak

 Source: GQ

Just like anything else, becoming a better dresser takes time and practice.

One thing that people continually forget is that in understanding the rules of style and becoming more comfortable with proper fit, it takes a lot of trial and error. And it's completely okay.

During my "style improvement journey," I can think of one too many times where I dressed pretty sloppily, wearing overtly baggy jeans or old T-shirts that were three sizes too large. As time went on though, I started shedding those pieces in favor of more fitted and attractive clothing. It was a process (one that took years), and I'm still not at the finish line, nor do I expect to be anytime soon. It's a learning process, one that takes a lot of patience and perhaps some risk.

Also, I know I'm definitely not alone in going through it.

In this moment, I can think of two amazing menswear icons that have had quite drastic style evolutions in the past decade: Andre 3000 and Daniel Craig. Check out those links to see how their style has changed over the years.

To be frank, these folks clearly did not know what they were doing even as recently as a couple years ago. However, they continually experimented, sometimes wearing embarrassing and ridiculous clothes along the way, ultimately evolving into the excellent dressers they are today.

So in all, don't be afraid to take some risks and even make mistakes in this process of dressing better. We all go through it, and it will only help you make wiser decisions as you move forward.

The art of getting dressed

Mark Kwak


Before work, school, or just going out in public, we all stand in front of our closets and make a conscious decision on what we will be wearing for the rest of the day. This process fascinates me, as each and everyone of us is faced with the same dilemma, yet we all make different decisions based on our personalities or circumstances.

To some, getting dressed is merely a functional process of covering one’s body with clothing. To these people, it’s a matter of what can be reached the quickest, rather than what can look the best.

To others, it’s a ritual that must be painstakingly consistent, down to a T. Whether it be based on a rotation or season, these people need to be dressed a certain, unchangeable way, mainly to make sure they don’t break what’s working.

And of course there are people who think a bit more about what the occasions (and people) in front of them will look like, and try to dress accordingly. They want to portray themselves to the world in a certain light, and serve a tailored message to those who look at them.

I don't believe anyone is right or wrong in this matter; it’s all a matter of choice. However, let me tell you why I personally think the ritual of getting dressed properly in the morning actually matters.


To me, getting dressed is more than just putting on clothing. It's a time when I get to decide what type of image I want to put in front of others. Without speaking a single word, I will already have portrayed a certain message, swagger, and lifestyle just from the outfit I put on.

If I'm wearing thick gold chains, baggy acid-wash jeans, and high-top Jordans, I'm clearly sending a different image for others to identify me by, than if I'm wearing a black suit and tie. And as you all probably know from personal experience, first impressions are incredibly important, almost unfairly so. So why wouldn't I want to carefully craft the message I send to others?

Now, people will argue that it doesn't matter what others think of you, or that people who judge you for your choice of your clothing are just plain superficial.

To some extent, I agree. We shouldn't take other peoples' opinions too seriously, and superficial judgement can be misleading or unfair. However, the truth is that we don't live in a world where other peoples' opinions don't matter at all. Your relationships, your decisions, and even your career are influenced by peoples' perception of you, and you have no way to avoid it. The moment you step out into the public, there are expectations of you, and if you want to gain respect or paint a favorable picture of yourself to others, you better make the right impression, which might include learning how to dress properly.

When you know the rules of dressing properly, and the types of clothing you need to attain, it will certainly pay off in the long run. The opposite sex- and same sex- may appreciate the effort, the level of respect you gain from the general public will likely increase, and you'll feel more confident about yourself, as your clothing will serve as an extension of you.

Also, whether we like it or not, people choose to interact with us differently based on our clothing. Walk into a luxury hotel with a baseball hat and baggy jeans; I guarantee the amount of service and attention you get will pale in comparison to when you walk into that same hotel with a sport coat. I've done these types of social experiments myself... and I can confirm it. I'm even thinking of making a video about this phenomenon.

So in all, I want to encourage you all to think about what you wear just a little bit more. Express, empower, and of course, be yourself through your clothing. Craft the message you want to send to others, and show them that you're willing to put in the effort.

By virtue of visiting a blog like mine, I'm confident you're already on your way there, but just in case, I thought I would reinforce the topic with this post. Of course in a billion words or more, in true Simpler Man fashion.

Signature Style: Dandy Dapper

Mark Kwak


Last week, I launched a series called Signature Style, where the goal was to showcase some very particular looks that might help you discover, or at least think about, your own signature style.

Today, we're checking out a look that is very common to the world of "dandyism."  A world of colorful tweeds, suspenders, paisley, fedoras, and lapel flowers. Again, like the Thom Browne look we discussed last week, this one probably isn't for the conservative or risk-averse.

This particular style fascinates me, and I actually love it, even if I don't sport it myself. I see it occasionally on the streets, but it's in fashion magazines or albums of Pitti Uomo that I really see it in action.

I always wonder what brings people to wear this type of attire. Celebrity figures like Andre 3000, Common, or Sean Combs regularly sport these types of outfits, and I'm finding that more and more people are following suit.  Maybe it's in order to exercise freedom of expression, letting everyone know that anything and everything is fair game. Or perhaps it's to push the envelope in menswear a bit, giving a forceful middle finger to the casual T-shirt and jeans look that we're all so familiar (and bored) with.

Either way, I wanted to at least bring it to your attention so that you can decide for yourself whether it's a style you'd like to emulate or not. Here's my buddy Ron sporting the look with ease:


 I wanted to make this outfit pop by incorporating many patterns. Some might say it's too much, but in many ways, that's kind of the point. 


Accessories galore. This is where a man can really show his individuality. Bracelets, colorful socks, hats, pocket squares, bow ties. All fair game.


The key to making an outfit like this look good is largely about fit. It's still #1.


If you look closely, you'll see there's a lot of strategy employed in the accessory colors. Blues, reds, and yellows are carefully matched from shirt to bowtie to jacket. 


More than anything, a look like this really boils down to confidence. Simply know that you're looking good, and you're a majority of the way there.

 Hat: Nordstrom | Shirt: J.Crew | Jacket: J.Crew | Bowtie: Bloomingdales

Pocket Square: Turnbull & Asser | Watch: Timex | Trousers: J.Crew

Socks: Merona | Shoes: Allen Edmonds

Some of you may dislike the outfit, some of you may be fascinated with it. To provoke that type of polar reaction is actually kind of my point, and I'm glad I had the opportunity to style it for you. Personally, I think the guy looks pretty dapper.

One thing to remember is that even when wearing this type of clothing, you should pay attention to the way patterns & colors work with each other. In this particular outfit, each piece was carefully chosen to either complement, or purposely contrast other pieces in the outfit. The pocket square has hints of red that work with the bow tie, the bow tie has hints of blue that work with the gingham, the belt and shoes have a red tint that complement the bow tie, etc.

Anyhow, there's my second look for this series. Hope you enjoy it as much as I do. Cheers.


Signature Style: American Schoolboy Prep (the Thom Browne look)

Mark Kwak

Source: Camodiaries

I've mentioned this before, but I think everybody has their own signature style. You can probably picture several of your friends right now, wearing what you would consider their signature pieces. The buddy who can't be seen without his blue baseball cap and Ralph Lauren polo. Or your coworker that wears such rugged boots and jackets that it looks like he's ready to go on a hunt at any point in time.

But what about you? Can you identify your own signature style? Is it something you stand by? Personally, I think it's important that we all discover the look we're most comfortable and confident in, and move in the direction of making our signature style embody that look.

To help in this endeavor, I've decided to launch a small series called Signature Style, where I showcase outfits that I believe represent certain signature styles we may encounter on the streets. Hopefully these styles will give you some ideas or inspiration for developing your own signature look.

To accomplish this task, I enlisted the help of some of my buddies, who agreed to model and demonstrate several looks that I have been wanting to put together for quite some time.

To make it clear, these are very particular styles that aren't necessarily what I deem classic or simple. However, I think that the slightly exaggerated nature of these getups can help you identify what works for you and what doesn't. Taking ideas here and there, and then ultimately putting together your own unique look is what really matters to me.


The first signature style I put together is that of one of my favorite designers, Thom Browne. His style is one I personally like to call:  American Schoolboy Prep.

For those of you who are unfamiliar with Thom Browne, he is a very fashion-forward designer from New York, who sort of revolutionized modern menswear tailoring. Have you noticed trousers are getting shorter and shorter these days? Well, in many ways, we have Thom Browne to thank for that. Have you noticed folks wearing dress shoes without any socks? Again, Thom Browne. Red, white, and blue grosgrain trimming? Thom Browne.

Truth is, his look is not one for the insecure or conservative. He starts with seemingly classic American outfits (like a flannel grey suit), but then cuts them in ways that make you wonder if the man wearing them is wearing his son's clothing. Trousers are cut too short, sport coats end closer to the hip rather than the thigh, and knitwear is skin tight. To illustrate, I've put together this look for my buddy Grant:


As you can see, this outfit is very similar to Thom Browne's one at the top of this post. White oxford button down, gray sport coat and trousers, gray tie, brown bluchers, and a white pocket square.


I wanted to make sure this outfit was monochromatic, with gray acting as king.


I also wanted to work with various wool textures and patterns. Got some herringbone and specked designs, all over cashmere and flannel fabric.


Chunky brown wingtips, no socks, and trousers cut 2 inches too short. Pure Thom Browne.


Also, I believe using thick, plastic rimmed glasses really finishes off the American schoolboy look.


Though this look is trendy and on the up-rise, I honestly wouldn't advise going into the office this way.


Glasses: Warby Parker | Shirt: Jack Spade (in blue) | Jacket: Black Fleece | Tie: Bloomingdales

Pocket Square: Jos A Bank | Cardigan: Gap | Pants: Uniqlo | Shoes: Alden

There you go, the American schoolboy prep look... a look that I'm quite intrigued by these days.

If you live in New York City, you'll probably see these types of outfits donned by avant-garde fashionistas from time to time. It's blowing up in the fashion world, and for good reason.  I think it brings something new to the table, combining a very particular form of modern tailoring with what we've always considered traditional American style.

Anyhow, hope you can take something away from this outfit, whether positive or negative. Oh, and look out for the next part in this series where I go over dandyism.