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

Filtering by Category: Simpler Woman

Thoughts from a Simpler Woman: Summer Getaway Outfits

Mark Kwak

It's been a while since the last simpler woman post, and I want to make sure we don't fully lose sight of the female perspective here at Simpler Man. Thus, I bring to you the next edition of Simpler Woman, written by my very fashion-forward friend Sarah. Also, this post comes just in time for summer. It's all about dressing the part of being on vacation, but still looking stylish as ever.


Summer Getaway Outfits

With summer travel around the corner, it's time to check out the best outfits to pack for your beach or resort vacation.

First things first: you can't have a beach vacation without swim shorts. I recommend ditching the board and surf shorts to modernize your look. Show me some leg, gentlemen! The Curtis from Saturdays Surf NYC is a favorite of mine. With a 15" outseam, it won't feel too short, but at the same time its length will move you away from that beach bum look. Plus, they have pockets, so they can double as shorts to wear into town after a day on the beach.

Once you have your swimwear, think about how you can stylishly double your beach wear into an outfit that will extend through the day. You can look effortlessly chic by pairing a soft, high-quality solid color tee with your new swim shorts. Put your plastic flip flops away and throw on a pair of Sperry Top-Sider boat shoes. Now you'll be ready to hop aboard your yacht:

Also, make sure you've got your eyes protected in this hot weather! I always fancy a vintage Ray Ban aviator; it'll give you an edgy allure and you can try a different type of Ray Ban than the Wayfarers.

Heading to a waterfront restaurant for a mai tai this evening? For casual dinners or nights out on the beach, I recommend a linen button down. I love the Mediterranean feel of linen shirts, especially in white. Perhaps these really attractive Brooks Brothers ones?

You can pair the shirt with a pair of jeans or chinos from Bonobos. Their Summer Weight Chinos are a lovely material. Or, try the Travel Jeans that can double up as both your airplane pants and your going out pants! If it's too hot, you can still rock shorts at night, just make sure to keep away from cargos and other casual styles. Instead, spice it up with some patterns or colorblocking, like these Club Monaco shorts!

Hope this gets your suitcase packed! I better start working on mine next...

sarah maldives

Sarah is an avid traveler, wine lover, and fashion enthusiast. Today, she can be found in either San Francisco or Chicago, daydreaming about her next summer vacation.


Thoughts from a simpler woman: Bold Accessories

Mark Kwak

It's that time again. That time where I disappear for a bit, and bring to you a more important perspective on menswear than my own- a woman's. If you haven't checked out my previous "simpler woman" posts, you should definitely take a look. Here they are for you: 1 , 2 , 3 .

Today, we'll hear from one of my old college friends, Emilie. She's a fashion guru at heart, but also kind of a bonafide genius in pretty much every subject known to man (cough... that one Boston school... cough.... 4.0 galore). Thus, it might be worth it to listen to her advice.


Bold Accessories

While I cannot quite put my finger on it, there is something about a man who enjoys the simple pleasures in life that catches my gaze.  You know what I’m talking about.  It’s that guy at the corner coffee shop who takes his drip coffee in-house, absorbed in a dog-eared copy of the WSJ.  It’s that guy who enjoys a quiet whisky on the rocks after a long night at the office.  There is just something about a man with the confidence to enjoy the small pleasures in life.

Style is no exception. It’s that extra bit of bold execution, shouting adoration for life, that brings a grin to my curious eyes.  What better way to exude this sort of boldness than through tastefully-placed accessories? To me, the unexpected burst of color and whimsy can add so much to any man's outfit.


Audacious socks that peek out from beneath an ensemble of dark slacks and a pressed button-up bring a hint of fun to the usual dark getup.  I’ve met my fair share of corporate men and it’s the ones that can make me laugh and bring a little humor that can make or break an evening.  Though you may be fenced behind a corporate lifestyle, a bit of unexpected cotton color hints at your affinity to flirt with life.

BOSS dress socks

boss socks

Simply Bold

A simple, bold watch hints at those nostalgic Calvin and Hobbes days.  Only now, the kid behind that grin is a youthful, twenty-something with a quick wit and an easy laugh.  Not every workday mandates a Patek Philippe dripping from your wrist.  With ease and some confidence, a playful watch will definitely invite a few grins your way.


Tic O-Clock Watch  


Eyeglasses are a statement piece.  Forget the wire-rimmed spectacles that scream “I was an extra on Office Space.”  The subtle sexiness of a well-read man doesn’t escape us women.  Frame your face with a pair of fun edges.  We won’t be able to stop ourselves from imagining tossing those rims bedside later…if you ever happen to look up from that copy of the WSJ.  Have a little fun with an unconventional pair of specs.


Oliver Peoples NDG-1


Emilie Simpler WomanEmilie, a Bay Area native, and recent convert to whiskey, currently lives in Boston.  In between hitting the books, she loves to get her travel on and restaurant visits in.  She thoroughly misses San Francisco (if anyone is willing to send her some Philz coffee beans, she will forever be delighted).

Thoughts from a simpler woman: Grow up!

Mark Kwak

It's time for another edition of “Thoughts From a Simpler Woman,” where I bring to you a woman’s perspective on menswear. In case you missed the first couple posts in the series, here they are: 1 and 2. Today's post is all about growing up and upgrading your high school, college, or for some of you, post college wardrobe. My friend and colleague Allison will be taking the reigns on this one, and she's one of the most fashion-conscious people I know. Now that I think of it, she was one of the first people I consulted before starting Simpler Man. It would be wise to listen up!


Grow Up!

Not everyone out there is as stylish as Mr. Simpler Man.  But even if you aren’t a GQ subscriber, putting a bit of effort into your personal style can make a difference.  Don’t believe me?  According to a joint study by Harvard Medical School and Massachusetts General Hospital, first impressions are established in just 250 milliseconds (a quarter of a second).  For those of you looking to nail that interview, charm on a first date, or just come across as a put-together dude, I hope these tips can help.

My first piece of advice: grow up!  If you’ve been wearing the same thing since high school, chances are you need to upgrade.  Not sure where to start?  Here are some of the top offenders I’ve seen as a Simpler Woman:

1. Instead of The Embellished Hoodie … Try a Hooded Jacket

From this:

To this:

I know, I know - they’re comfy.  They’re practical.  And I’m pretty sure everyone I know, including myself, has had one at some point in their life.  But trust me, it’s time to let this one go.  The good news is, you don’t have to go to extremes.  I don’t expect you to go straight from hoodies to a suit.  Instead, try a hooded jacket.  This one from Banana Republic is a good example of taking the major features you love in a hoodie, but done in a tweed-like texture in a neutral color.  Ahh, much better.

2. Instead of Sneakers … Try Desert Boots

From this:

To this:   

Let me be clear: I’m not saying that you can’t ever wear sneakers and be stylish (that being said, there could definitely be a whole separate post about fashionable vs. non-fashionable sneakers).  Sure, there is definitely a time and a place for them in a simpler man’s repertoire.  But they shouldn’t be the first thing you reach for, and certainly not your daily footwear of choice.

If you’re particular about your shoes, and won’t sacrifice comfort for style, take a baby step and try desert boots.  Clarks’ version pictured here is a classic for a reason - they’re extremely versatile, and never really go out of style.  For a plethora of great looks featuring desert boots, check out men’s style blog Street Etiquette (my second favorite, of course):

3. Instead of Velcro … Try a Leather Wallet

From this:

To this:

Okay, okay - this one is a bit of a joke.  Or is it?  Just to be safe, I’ll make myself clear: invest in a nice wallet.  Velcro, chains, and duct tape probably won't get you very far with the ladies. Enough said.


simplerwoman allisonAllison is a food, tech, and style loving San Franciscan.

You can catch her in the city making Tartine bread, consulting people on their startups, or helping guys dress better. 

Photo Credits:,, Banana Republic, American Eagle, Zappos

Thoughts from a Simpler Woman: Travel in style

Mark Kwak

A couple weeks ago, I started a series called "Thoughts From a Simpler Woman," where I brought to you a woman's perspective on menswear. In case you missed it, here's the first part of the series, which went over some essential pieces that belong in every man's wardrobe. In this post, I'm continuing the series, with the help of my friend Stephanie, who is both an avid traveler and fashion enthusiast. She's a Hipmunk marketer by day, and trendy fashionista by night... someone who you might want to listen to.

Today, she'll be discussing a topic very near and dear to both of her passions, giving you advice on clothing you should wear while traveling. Now, without further ado:


Travel in Style

I’ve done my fair share of traveling, and if there’s one thing I know to be true it’s this: you never know who you’ll meet while traveling. Whether for business or leisure, a one hour or twenty-one hour flight, you should always be dressed to impressed. Your peers may be sporting sweatpants for comfort, but let’s be honest -  a future love interest, colleague, or celebrity, will not make small talk with someone in their sweatpants. So how exactly does one dress comfortably for a cross-country flight, yet still look polished enough to get bumped to first class? Here's the perfect outfit to wear while traveling.

1. Casual button-up.


Choose one that both fits well and is comfortable to wear while seated for long periods of time. T-shirts can make you look sloppy and disheveled. Airlines certainly don’t upgrade those who wear t-shirts to first class. If you want to keep pretty casual, I like these chambray ones from J.Crew.

2. Cardigan.

Any seasoned traveler knows to layer. A classic cardigan or sweater not only adds another dimension to your ensemble, but will help co mbat the airplane’s circulated cold air. It’s truly a utilitarian piece. Here's a pretty affordable one from Topman.

3. Simple raincoat.

Screen Shot 2013-02-28 at 1.02.17 PM

A simpler man should always be prepared without exerting too much effort. Traveling with a light raincoat assures that you’ll be ready to face whatever the weather may be at your final destination. Choose a coat that you can easily take off and fold during your flight. Try a parka like this by Land's End.

4. Slip on loafers.

Loafers are refined, yet casual and versatile. They are a great option for flights because you can easily slip them off, and quickly get through the security line. If loafers aren’t your style, try a slip on boot - just avoid anything with laces. I know these are expensive, but I'm a fan of these by To Boot New York.

5. Tab closure pants.


Wear nice pants. Don’t wear basketball shorts, sweatpants, or even lululemon workout pants. Men, wear actual pants when you travel. There are plenty of brands that make pants you’d love to wear while sitting for hours. If you don’t want to hassle with a belt at the security line, opt for tab closure pants. And please, wear a slim fit.

6. Carry on.

Last but not least, have a decent carry on bag. Nothing crazy - both Louis Vuitton and your old high school gym bag scream unapproachable. A great carry on bag is like the cherry on top of your stellar outfit - don’t overlook it. For lighter travel, try a duffel or weekender, for longer trips, a simple rolling bag is best.

There you have it. All you need to ensure that you’ll never look frumpy at your terminal. If anything, I'll certainly appreciate it.



Steph Bio PicStephanie is an avid traveler, visiting a total 13 countries and counting. She's zip-lined in Costa Rica, food tasted in New Orleans, and backpacked across Europe. She also made sure to stop by Milan, London, Paris, and New York, just to experience the highlights of international street fashion.


Picture Sources: J.Crew, Nordstrom, Everlane, Land's End, Bloomingdales

Thoughts from a Simpler Woman: 3 Men's Wardrobe Basics

Mark Kwak

Let's be real. About half of you visit this site, as well as other menswear blogs, to learn how you can impress the ladies with your impeccable style. There's no shame in admitting this, we all know dressing better can garner more attention from the opposite sex. For this reason, I've decided to start a guest-blogging series where you can hear from women directly, on how to dress better. Today, it's all about 3 staple pieces that every man should have in their wardrobe. All brought to you by my very stylish, San Francisco living, dog-loving friend, Kristin. Read on:


3 Men’s Wardrobe Basics That Will Make This Happily Married Woman Turn Her Head for a Second Look

It does not take an extravagant show of style, the latest fashion runway look, or an expensive designer brand to make me to elbow my husband and say, "See, you need a basic (insert clothing item here) just like he has, that looks so good!" Because actually, in the vein of the mantra of this blog, it really is quite simple.  The simpler the fashion, the simpler the man, the simpler it is to get the approval of the ladies.

I have faith that as a reader of this blog you are already doing a lot of things right.  You aren’t wearing denim with patterns or embellishments on the pocket, you definitely aren’t pairing a suit jacket with a pair of jeans in an effort to look ‘casual yet important’, and the absolute only time you wear a hoodie to dinner is when you are grabbing something to go on a weeknight.  Right?  Right.  But enough about what I know you are already doing, and on to the wardrobe basics you should most definitely own:

1)  Dark jeans.

Buy a pair & wear them every single time you are even slightly unsure of what to wear.  As a solid base to the rest of the outfit, I believe a guy almost can’t go wrong no matter what other fashion decisions he makes.  No stone wash, no holes, no embellishments, no fancy colors.  Just a pair of straight fit, dark blue jeans.

Such as these always stylish APC New Standards.

If you are intimidated that you might go wrong in your selection, I have witnessed miracles in the Men’s denim department at Nordstrom.  I guarantee they can have you in and out in 20 minutes with your new jeans.  And while you are there, perhaps you can browse for…

2)  A pair of sunglasses that aren’t black Ray-Bans.

Last year after Coachella, the organizers posted on the Coachella website a notice that went something like this, “If you lost your black Ray-Bans during Coachella weekend, be advised that so did everyone else so you are out of luck in getting them back.”  I breathed a sigh of relief knowing so many black Ray-Bans had been cleaned from the sunny California streets.   But it wasn’t quite enough so my advice is that you should too keep your black Ray-Bans where they belong:  music festivals and Men in Black auditions.  And find another pair of every day shades.

I like these by Persol, but really anything other than black Ray-Bans is a great start.

3)  Plain t-shirts.

You’re a guy so there is a high probability you are going to do it anyways, so all this lady asks is that you do it with a bit of class.   Invest in high quality, plain cotton t-shirts in non-neon colors that you cannot see through.  That’s it.  If your t-shirt has something to do with sports, you’ve messed up on this piece of advice.  If you bought your t-shirt on a brewery tour, you’ve messed up.  But your t-shirt has a cute dog on it that says, ‘Pugs not Drugs’?  That is cute, but no.  In fact, if you bought any t-shirt from a display at Urban Outfitters, you’ve probably messed up.

This is so easy to do, and cheap!  Try these from J. Crew.

Hey now, look at you with your dark jeans, your shades, and your nice t-shirt!  I love it!  You can keep it simple just like that, or you can add on virtually any other new item you have acquired based on the fashionable inspiration you have received from Simpler Man.  And when I see you on the street, I’ll take a second look, and elbow my ripped-old-jeans-wearing, RayBan-sporting, Indiana-basketball-t-shirt-styled husband to say, “You need to dress like that!”  To which he will inevitably roll his eyes and respond, “Cool it, honey.  You’re married.”

kristin for blog

Kristin lives in San Francisco with her husband, Chad, and miniature dachshund, Wrigley.

She's also a style guru, so you'll want to take her advice.