How Men Should Dress For Every Occasion | A Complete Gentleman's Guide

Posted by Rishi Chullani on

Alyssa Breeden

Dressing dapper has been a conundrum for men longer than the Spice Girls have been trying to convince us that they are real artists. Figuring out what a dress code is, and then how to dress appropriately for it, often feels harder than solving a game of Sudoku with Kim Kardashian. With that said, here is our comprehensive (yet well summarized) guide to how men should dress for every occasion! Whether you are dressing casual, for a dinner date, an evening out, work or an interview, this insightful guide will ensure that you are always dressed your best, irrespective of occasion!


If you are planning to grab pizza with some friends or head out to your local bar, it’s probably best to stick to casual. Even so, it’s still important to present yourself in a way that makes people want to respect you.  You should always step your style up for a social event.  Everywhere you go, everyone that you encounter – you are creating lasting impressions – make them count.  

For a casual night out, try wearing a pair of great-fitting jeans and a nice, collared shirt.  This may also be an opportune time to pull out that funky blazer that you have been dying to wear. 

Sometimes neckties are great, other times they are not needed. They are certainly not expected in most casual situations.  However, when choosing a necktie, you should choose a sophisticated design that adds flair but does not outshine your situation.  Try a go at one of our knitted ties, they are both casual and oozing with cool.

 Knit Ties Casual Wear

A Knit Tie can instantly elevate your casual ensembles. Courtesy of Men’s Style Blog He Spoke Style.

Be sure to pay attention to the small details like your belt, sock, and shoes – as they can speak volumes about your personality.  After all, anyone can pull off a green polo and look okay, but if someone has on striped socks and someone else has on plain white their separate personalities begin to unintentionally shine through.

Thinking that this all seems a bit too formal?  Our bracelet collection could be all that you need to set yourself apart and look great at your next casual event.

Casual Men's Attire

A Leather Bracelet is a great way to set yourself apart in a casual setting. Courtesy of


Date Night Attire

Layering on date night will elevate your style by at least a few notches! Courtesy of

For any date we recommend a classic and refined look that speaks to your great personality.  You want to be comfortable.  If you are not, it will absolutely show.

The first thing to consider is whether or not this is your first date with someone that you have never met before, someone that you have met previously but never dated before, or if it is someone that you have been involved with for many years.

Depending on the situation depends on what you may be able to get away with – meaning that you may be able to wear that quirky tie as a joke on a date with your wife but not so much for the first date with someone you’ve never met.  The new girl may not understand that this is your personality and may interpret your choice of attire as childish.

For any date, it is a good idea to dress in layers – sports jacket, pocket square, nice shirt, khaki pants.  The jacket ensures that you have ample room for everything that you need, plus you can take it off you get uncomfortable. A nice jacket will also make your date feel more respected (because you thought that the situation was deserving of something more than a t-shirt) and give off an impression of stability and responsibility.  Want to take it up a notch?  Throw on a timeless necktie.

Looking for a classic necktie that screams, “I have a cool personality”?  Our Skinny Fairfield Plaid is the perfect tie for a first date.  Not only does it come in a modern, sleek design, it is also available in both lilac and light pink.  Fairfield Plaid’s soft and subtle palettes work to delicately enhance your look.

Women care about appearance and are drawn to attractive men.  If your clothing is put together correctly, you can strengthen your good traits and downplay the not-so-great ones.  Win, win, win!

Please feel free to view The Dark Knot’s range of Date Night Ties!

Pocket Squares | Silk Pocket Squares | Linen Pocket Squares | Buy Pocket Squares | Shop Pocket Squares



Maybe you’re headed to the theater?  Maybe you’re going to try that amazing restaurant that you’ve been dying to visit, or you are off to a Hollywood party – either way, you are going to want to look your best.

How Men Can Dress For An Evening Out

Courtesy of

Slim lines and darker colors are going to be the best choice in this situation.  Anything too loose is going to make you look too relaxed and sloppy, resulting in bad impressions all around.

Mixing formal and business casual should give you a great balance for an evening out.  Grab a subtly patterned shirt, a nice jacket, and a slim tie for a great look.  This is also a great time to pull out those polished oxfords that you keep for “special occasions”. 

A few good options for this look are our Amesbury Paisley and Dartmouth Abstract silk ties.

Please feel free to view The Dark Knot’s extensive range of Evening Silk Ties


How To Dress Preppy For Men

Few things scream preppy like a seersucker shirt! Here, we have this item perfectly balanced by a green striped tie. Courtesy of

Not all of us encounter many preppy situations but those of us who do have a strong desire to fit into our surroundings. Whether you’re heading to the Kentucky derby a beach wedding, tennis in the park or golf match you’re going to want to look your best and (most of all) not boring.  This is the opportunity to pull out your best and brightest colors and your funny and funky ties. 

Though this may seem like a great opportunity to don a funky bow tie, be careful.  Some body shapes and shoulder structures are not very complementary to bow ties.  They can instead make you appear very short and clownish.

For a more formal event, go all out with your seersucker and straw hat.  Less formal?  Try wearing a pair of nice chino shorts and a solid shirt (light pink, green, yellow, blue).  Grab your seersucker jacket and try out one of subtle our animal print ties.

Please feel free to view The Dark Knot’s extensive range of Preppy Ties!


It is best to keep it simple during a first job interview.

It is a good rule of thumb to research the company’s dress code before the big day.  Not all company policies are the same – startup companies have the reputation for having more relaxed environments, while law offices tend to steer towards more traditional environments.  While we do recommend dressing to the nines, we do not want you to stick out like a sore thumb.

Color psychologists often encourage interviewees to wear a nice blue suit, as it tends to relay feelings of trust and friendliness to the interviewer (leaving a great impression before you even begin to speak).  A white shirt is the best shirt option for this look, as the color white often correlates with truth and simplicity.  You cannot go wrong.

Navy Suit Interview Setting

A navy suit will allow you to be at your professional best during an interview setting. Courtesy of Black Lapel

As far as neckties and accessories go, it is best to stick to conservative prints, or solid colors, during interviews

A few of my favorites include: Berkshire Abstract, Waltham Dots, and Montague Foulard.

Be sure to examine your clothing beforehand.  Make sure there are no wrinkles or stains and ensure that your attire has been professionally cleaned before you even think about donning it for an interview.

Need more help with your interview?  There is a ton of great information in our previous post, How to Dress for an Interview.

Silk Ties | Ties | Neckties | Extra Long Ties | Buy Ties | Shop Ties


If you are employed and happen to work in an office you are likely to find yourself in one of two situations, business professional and business casual.  In this section we will examine business casual attire.  If you are interested in a more business professional look, keep reading into the “work presentation” section as those looks tend to overlap.

How Man Can Dress For Work

A Sports Jacket provides for an incredibly elegant, yet understated look for a business casual setting! Courtesy of

In a business casual work environment jackets are still preferred, but not required.  You are likely to encounter most guys in the office wearing a navy blue blazer with khakis and a conservative tie.  However, it is also completely acceptable to wear a sweater over a dress shirt and tie.  In any situation be sure to have a nice pair of dress shoes and socks to keep your look balanced and neat.

It is within your best interest to always bring a jacket to the office, you can always take them off as the day progresses.  This is helpful for two reasons: (a) your co-worker Don can not handle the heat of your (already cold) 65 degree office and will not stop touching the thermostat and (b) you may find yourself called into an impromptu meeting with the CEO and guess what?  You dribbled your lunch.  Saved by the blazer. 

Keep in mind that it is never acceptable to show up to a business casual work environment without a collar on your shirt.  Honestly, aside from a ball field, there are not many situations where a non-collared shirt is preferred.


Maybe you have a presentation at work; you will need to fully evaluate your situation beforehand.  Have you had the job for forty years and have just built a marketing campaign that you need to present to the entire company?  Or did you just recently start and are heading into a room of people that you have never met?

You are going to want to look as professional as possible and here’s how we can help:  first you want to get yourself a classic business suit.  A business suit means one thing, a matched set.  Opt for a darker colored solid or pinstriped suit paired with a powerful tie.  You will also need a crisp shirt, clean shoes, and nice socks. 

How Man Can Dress For A Presentation

Few things are as quintessential to a presentation setting as a solid navy suit. Courtesy of

A watch is essential here as it shows that you care about being punctual and are a leader.  You will show everyone how responsible that you are without even saying a word. 

Need some help choosing a powerful tie?  My personal favorite is our Canterbury Regimental Stripes in red and blue – a tie that demands attention and respect.

Please feel free to view The Dark Knot’s extensive range of presentation ties!


Black Tie Attire

Black Tie Attire, when executed well, will instantly elevate your look! Courtesy of Men's Style Blog, He Spoke Style

The black tie event seems pretty straightforward; you dress your best, wear a black tie and look awesome. But what does that really mean and is it possible to stand out among the crowd?

Black tie events are generally more formal than the parties and events that you may be used to.  You are going to need to take your style up a notch for the evening.  We recommend wearing your best tuxedo jacket and matching pants paired with a crisp, white shirt.  

Traditionally, men are expected to show up in their best black bow tie.  Maybe it’s just us, but we opt for long skinny black ties rather than bow ties because they provide a more polished and modern look.

Your minor accessories are going to be important here.  These are going to be the things that set you apart from the crowd.  You can choose from several different shoe types, sock patterns, watch faces and bands, or you could add a pocket square – each with its own personality and ability to make you shine.


How Men Can Dress For A Wedding

Courtesy of Wedding Wire

Oh, lucky you!  Looks like your friends are getting married and you don’t know what to wear.  No fear we can help.

You are first going to want to evaluate the atmosphere in which your friends have chosen to get married in.  A summer beach wedding is going to be different than the Grand Ballroom at the Ritz Carlton.  Ask yourself - What kind of people are going to be there? Are you in the wedding party? If you’re in the wedding party, lucky you, you probably have your outfit chosen for you.

Mix and match the above situations to best suit your environment.  You might even revert back to our previous post for inspiration.  Does it still seem like nothing quite fits?  Just head over to the site and browse our “wedding” selection for inspiration and ideas.

That’s a wrap for this one! We hope this guide detailing how men should dress for every occasion helps you along your journey to great style!

Please feel free to view The Dark Knot's range of ties based on occasion! 


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