How to be a Sharp Dressed Man (as told by a Woman)

Here are my qualifications for writing about men’s clothing:

  1. I like clothes.
  2. I like people.
  3. I’m observant.
  4. I have opinions.

Those are pretty good reasons, but I don’t have any specific qualifications.  For instance, I don’t fully understand men’s sizing charts.  So I will caveat the heck out of this post and put in many disclaimers along the way, like the conscientious data researcher I am.  I just want to tell the truth and be helpful.  Those are two of my main goals in life.

Gentlemen, get out your notepads and pencils, because I’m going to tell you how to step up your style.

Men tend to change their style at life transition points – when they leave for college, when they start a new job, when they start dating, when they get married, etc.  Women tend to change their style when they when feel like they need a life transition.  That may be one of the reasons why men’s style hasn’t changed drastically in the past hundred years.  The materials and fits have changed, but there is more equilibrium and stasis in men’s clothing.  If one of my brothers wore my grandfather’s navy blazer, it would look sharp, but it wouldn’t necessarily stand out.  If I wore my grandma’s dress, people would say, “It’s so retro!”  Women’s fashion changes more.  Men tend to keep their clothes for longer and wear them out.  That’s why most thrift/vintage/consignment stores will have more limited selection for men – the men are still wearing those clothes or the clothes are completely worn out.

So if you are at a transition point and want to change your style, here are a few things to keep in mind.


Men, fit is the most important element of style for you.  Let’s break down how individual pieces should fit:


A good shirt will fit through the shoulders without pulling.

You’ll be able to tell if the shirt is pulling if there are stretch lines across the back or gapping buttons in the front.  Now, I know it’s easy to avoid the tightness problem by going too far in the opposite direction, because I’ve seen tons of guys wearing shirts that are two sizes to large for them.  You can tell the shirt is too large when the shoulder seams are too wide and do not hit your shoulder.  If the shoulder seam is somewhere on your upper arm, the shirt is way too big.

The shoulder fit is the most important.  The second is how the shirt fits through the body (basically everything that isn’t sleeve).  Most of the time guys do not tell me their fashion woes.  I am left to figure their woes out on my own.  But the rare exception is shirt fit – they tell me all about that problem.  Apparently, it is very difficult to find a shirt that is long enough without drowning in excess material.  In America, there’s a preconceived notion that if you are tall, you are also wide.  If you are tall, but not wide, it’s probably best to search for slim fit shirts.

If the shirt fits through the shoulder and the body, the sleeves and collar are the last and finest details.  The ideal sleeve fit long enough to hit just past the wrist bone and show just a sliver of the shirt when you are wearing a jacket.  The ideal sleeve width is wide enough to be comfortable and allowing for movement, but not poofing out.  We should know roughly what your arms look like and you should have enough room to roll up your sleeves if you want.   (Disclaimer:  I know that some fancy shirts do not have sleeve buttons and require cuff links.  I honestly don’t know much about cuff links.  If the shirt fits well, how the sleeves fasten doesn’t matter much to me.)  As far as the collar goes, you should be able to button it without choking to death.  That way you can wear a tie without looking like your are attending your own hanging.  Believe me, I’ve seen many grown men look desperate at the mere thought of putting on a tie.  Well, tough.  Ties are required sometimes and that’s just how the world works.  I was asked about my opinion on collar buttons and I’ve thought about it.  I don’t mind them, but I think a collar looks cleaner and sharper without buttons.  That being said, they look fine – they just make the shirt look much less formal.  They make me think of checked farmer’s shirts, which I have a great fondness for, because my dad is a farmer and he wears his checked shirts every day and they suit his job.  For a formal shirt, I would look for one without collar buttons.  For a work shirt, wear whatever suits the work you are doing.

Now I can hear what you are thinking.  It sounds very difficult to find a shirt that fits in all those ways.  Wouldn’t it just be easier to wear clothes that are a size too big and not worry about the sizing?  Yes.  It would be easier, but easier is not the goal here.  I want you to look handsome, respectable, and like you care.  I don’t want you to look like those high schoolers working at Olive Garden who were told they needed a white shirt, so they all buy identical oversize white shirts to wear with their restaurant-official black ties and aprons.  Do they look like they want to be there?  Nope.  Looking like you care counts.  It counts for a whole lot.  The bar is set very low for men’s style and you can easily go beyond looking okay.


Don’t worry – trousers are much simpler than shirts.  Trousers should fit at the waist with enough room to tuck your shirt in.  Ideally, they should fit well enough that you don’t need a belt, just in case there’s an emergency and you need your belt to make a stretcher or a tourniquet or something.  You don’t want to be overly dependent on the belt.

They should be long enough to touch the top of your feet.  I don’t want to see your socks when you’re standing up.  When you sit down, your trousers will get a bit shorter and then it’s okay to see your socks, but if your shoes are leather, those socks should not be white.  White socks are okay with sneakers or slip-on canvas shoes, but if you are wearing white socks with dress shoes, I’ll disown you.

Jeans should be worn loose enough for comfort – your comfort and the comfort of others.  Also, there will never be such a thing as dressy sweatpants.  They just look like pajamas.  I know that “athleisure” is a fad right now, but it’s already on its way out.  The athleisure trend has been great for the people who primarily wear workout gear, but let’s not kid ourselves into thinking that it looks dressy or professional.  Athletic clothes and sweats are great for working out in and sleeping in and taking your friend to the airport at 3:30 in the morning, but not for work. Not even the grocery store, really.

Jackets & Suits

I love jackets.  If you live in a climate that is too hot for jackets, I’m sorry for you.  They cover a multitude of fashion sins.  Most shirts look perfectly fine under a blazer, even the ones with stains or big sleeves.

If you are in a climate that allows for jacket-wearing, I highly recommend them.  A good jacket should fit through the shoulders (are you sending a theme here?), have enough room to fit over a shirt and a light sweater without looking lumpy, and sleeves that hit at the wrist bone.  A jacket doesn’t have to be formal, like a blazer or a sportscoat, but those styles do look great.  Bomber styles or basic jean jackets can be versatile casual options.  Here’s the rule – the more casual a jacket is, the larger it can be, because you need to do more in it.  If it is too tight to work in, it’s impractical.  The more formal a jacket is, the better it needs to fit.  That goes for most clothes.  The clothes need to be appropriate to the situation.  Speaking of appropriate situations, let’s talk about suits for a minute.

I think every grown man should own a suit.  There’s probably at least one guy out there who thinks he has absolutely no use for a suit and never will in the future either.  If you know any people at all, a suit will be appropriate at some point in your future.  Weddings, funerals, business meetings, interviews, parties.  There will be important times you are called upon to celebrate, to mourn, to witness, to take joy in.  The older you get, the more you will be called upon, because you will know more people and have more responsibility. Suits show respect to other people and, in turn, gain respect from other people.  So work toward owning a suit.  If you can’t afford one right now, that’s a perfectly good reason to not own one, but start saving up for one.  It is a good investment.

There are specific rules for how the ideal suit should fit and how it should be worn.  Once again, the shoulders must fit well.  The sleeves should be slim, but allowing room for movement.  The trousers should not wrinkle up around the ankles – they should hang straight and just cover the top of the shoe.  It all sounds like something out of P.G. Wodehouse, doesn’t it?  It reminds me of the moment when Bertie Wooster asks his valet the important question, “There are moments, Jeeves, when one asks oneself, ‘Do trousers matter?'” “The mood will pass, sir.”

Jeeves, as always, is correct.  The trousers matter.

As to how a suit should be worn, the lowest jacket button should never be buttoned and the same goes for a suit vest.  Don’t button that lowest button.  It just isn’t done.  When standing, the top button should be buttoned, but you should unbutton all jacket buttons when you sit down.  That seems like a lot of math, but it’s fairly simple.  Two button jacket?  Just button the top one.  Three button jacket? Definitely button the top one, but the second button is optional.  Vests can stay buttoned when you are seated, except for that lowest button.  I only learned all of this recently, but it makes sense.  All clothes become more constricting when you sit.  The ideal suit should fit perfectly when you are standing, so the jacket would be a little tight to sit down in.  Nobody wants an overly tight jacket, especially at a dinner.

Wow – that post covered a lot. I don’t feel like I have room to really do justice to styling and accessories this week, so this will be Part 1 and next week we will go beyond fit and deal with shoes, ties, hats, haircuts, etc. Send me all your questions!

I hope at least part of this post was helpful – if not, please let me know! I am far from an expert on this and I love learning new things and hearing from you all.

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