What to Wear? (or How to Dress for the Occasion)

How to dress for the occasion.

What to wear?  What am I specifically wearing? Questions that I’m sure people ask me in their minds when they remark how well put together I am during the two days of the week they happen to see me.  I’m honestly not sure if people think I go home and throw on busted jeans and a torn t-shirt or if I don a full tuxedo.  This series, going forward, will be mostly pictures.  Every day I’ll snap a picture or two of myself and post them here.  For context, I’ll also note where I’m going or where I’ve been.  The hope is that I can effectively demonstrate what to wear and when.

Let’s get started:

February 1st
how to dress for the occasion
T-shirt and Dickies work pants.

Yesterday, Friday, for me was a homework day.  So I got very comfortable and hit the books.

February 2nd
how to dress for the occasion
Casual Button-Down
how to dress for the occasion
Brown Corduroys with Black Square-toed shoes


Today I had a monthly breakfast, with a committee meeting following, with my Fraternity.  Still casual, but not t-shirt and jeans.

Today’s post illustrates that there are many forms of casual.  From t-shirt and work pants, to a button-down shirt and corduroys.  Let’s not forget business casual!  Setting plays a large part of knowing how to dress.  If you’re unfamiliar with the setting, always dress at the upper end of the spectrum.  For example, if a corporate funded dinner says “business casual”, I would suggest slacks, sport coat, and tie if it’s your first time in that specific setting.

I may include brand descriptions in the future (and subsequently links to where items could be purchased), but the intent of these articles are not to promote any specific brands.  With that said, there are certain clothing items that should last you many years, so be selective with regard to quality.

(part 2) feat. a Navy Cardigan and Power Tie

(part 3) feat. Tan Cords and Brown Casual Shoes

(part 4) feat. a Med. Gray Suit with Floral Tie

(part 5) feat. a Tweed Sport Coat with a Vest and Power Tie

(part 6) feat. a Med. Gray Suit with Pink Tie

(part 7) feat. a Green Tweed Sport Coat

Men’s Fashion Dos and Don’ts: Part 1

A list of the top five dos and don’ts of men’s fashion.  This list is comprised of tips for a more timeless and less trendy look.  It is almost every gentleman’s opinion that a wardrobe should consist of more timeless pieces.

1) Neckties

Neckties, generally, should be a darker color than the shirt they are paired with.  Let me add that there will never be an occasion where a white necktie will be appropriate, ever.  In the world of men’s fashion, “white tie” refers to a bow tie, not a necktie.

Men's Fashion Dark Shirt Light Tie
This yellow tie with a black shirt is too contrasting, even for trendy.

For a more timeless look, attempt to bring a color from the rest of your outfit into your tie.  For example, a Red/Navy Honor Stripe tie with a navy suit.  Don’t think that you need a necktie of every color in the rainbow.  Instead, you will find yourself only wearing three or four different colors, but with many different variations of that color, i.e. style, material, hue, etc.

2) Shoes

The one thing every man needs to understand about men’s fashion is just how important shoes are.  You can go from business to business casual or business casual to casual by your shoes alone.  Shoes are extremely important for a gentleman’s wardrobe.  Don’t buy shoes in varying colors.  Black Oxfords are a great start to your shoe collection.  They most effortlessly match suits in navy, gray, and of course black.  After the black Oxfords, I would recommend brown Oxfords.  There are so many shades of brown ranging from colors labeled tan, tobacco, or for a more reddish variation, burgundy.  Make sure to get a belt that matches, which can be tricky, but a large shop will specifically have belts to match any color of shoe they have.  Brown Oxfords will match suits in navy and and, if your eye is sharp, gray.

3) Suits

If you don’t own a suit yet, don’t go out purchase a black suit.  Black looks too contrasting during the daytime.  It’s a color generally reserved for evening or night.  Navy or gray should be your first option.  I would recommend navy due to it’s versatility.  It can be worn morning, afternoon, evening, or night.  It has the option of matching black or brown shoes, and a lot of neckties match best with it.  Two piece or three piece?  That’s the question being asked nowadays.  Two piece, jacket and pants, may be a safer bet, but the three piece, added vest or waistcoat, is about as dapper as you can get.  I would say it varies greatly on the occasion, as well as your body type and comfort level.  This may be a question best answered between you and your tailor or retailer.

4) Shirts

Light blue, white, and cream should be your first choices on color.  Avoid black or very dark solid colored shirts.  These are left for the trendy folks.  The black shirt from the bad necktie example above is from my personal wardrobe.  I have only one tie in my collection that I feel properly matches it, pictured below.  These darker shirts are honestly best left to denim pants, aka jeans.  Patterns such as windowpane are excellent, but can be hard to find at large retailers who lean toward the trendy side of men’s fashion instead of timeless looks.  Button down collars are best left for the on-the-go businessman.  Someone who is more often seen in motion than posing for a photograph.  They’re considered sporty.  To best accentuate neckties, and especially bow ties, a nice spread collar shirt is the way to go.

Men's Fashion Matching Tie and Shirt
This black and silver paisley tie is an acceptable match for this black shirt, even if it is trendy.

Patterns such as windowpane are excellent, but can be hard to find at large retailers who lean toward the trendy side of men’s fashion instead of timeless looks.  Button down collars are best left for the on-the-go businessman.  Someone who is more often seen in motion than posing for a photograph.  Button downs are considered more sporty and less dressy.  To best accentuate neckties, and especially bow ties, a nice spread collar shirt is the way to go.  It will reveal more of your knot on a necktie.

5) Pants

Pants in men’s fashion is not an easy topic.  If you’re buying pants, it’s assumed you have a sport coat, or blazer.  I would recommend the classic navy blazer, which would pair with pants that are gray, either solid or patterned, or a lighter khaki variation.  If you opt for a tweed sport coat, equally timeless, pants will completely depend on the color.  Tweed comes in grays, browns, and greens most commonly.  Here’s the easiest way to match up a pair of pants.  With the exception of patterned brown tweeds, which will have other colors dispersed in the pattern, do not pair a similar color, or similarly dark or light, pant with the blazer.  Some patterned brown tweed blazers pair perfect with brown pants, but you may want to get a second opinion before purchasing or leaving your home.  Colors I keep in my closet are khaki, shale, brown, gray, and black.

There is a dominating trend in men’s fashion.  It revolves around denim jeans worn as business casual.  Do yourself a favor, stomp it out altogether.  There’s nothing wrong with wearing a nice shirt with a pair of jeans, but don’t confuse it for business casual, it’s just casual.  There are better options for causal anyways.  For casual wear, I recommend chino pants with any blazer that has a dull finish.  It’s very comfortable, with the exception of most winters.


The purpose of these articles are not give you unwavering rules and regulations.  The purpose is to keep you on the straight and narrow.  Men’s fashion is an ever-changing area, but personally I lean more toward timeless looks which will last my lifetime.  If you seek hardcore fashion advice and aren’t afraid of criticism, the gentlemen at Styleforum will generally set you straight.