in: Outfit Guide, Style

• Last updated: September 27, 2023

How to Build Your Wardrobe: Part III – Men’s Hats, Watches, and Other Accessories

Vintage black American man wearing hat and suit.

In How to Build Your Wardrobe Part I we discussed why a man’s clothing is important, broke men up into groups, and listed the clothing they need.  In How to Build Your Wardrobe Part II we gave you 5 general wardrobe building guidelines and expanded on the clothing checklists.  Now in How to Build your Wardrobe Part III, we’ll discuss hats, watches, and other accessories that add to a man’s presentation.

Four Simple Guidelines When Choosing Accessories

  1. Accessories add flavor to your clothing, but even great accessories cannot help a poor foundation –  If you haven’t read Building a Wardrobe Parts I and II, please do so.  I do not want you to form the impression that accessories stand alone – they do not.  Think of them like a spice; they can only bring out the best in a dish that starts with quality ingredients.
  2. Quality is good, meaning is great, finding an heirloom that embodies both is perfect –Some accessories are special in that they have lived a life before you, and within them is a sense of history and quality impossible to find in something new.  It’s a very lucky man who finds himself with his grandfather’s watch worn through World War II or a hat that was witness to Martin Luther King Jr. marching at Selma. Wearing a piece of history is special; it can give the wearer the strength to go out and create a bit of history himself.
  3. Use the accessory you purchase, and use it often – The writer Alan Flusser says it best in that the most expensive items a man owns are the ones he never uses.  Ensure that the accessories you purchase for your wardrobe are ones that will stand the test of time and that you’ll find occasion to use.  A handsome tie clip is wasted on the man who never wears a tie.
  4. Function first, style second….but not distant second– Most timeless men’s accessories serve a purpose – pay attention to performance first.  If you have to pay a little extra for style, weigh your options and then take the plunge.  You want something that not only works, but looks great doing its job.

A Man’s Accessories Overview

A Man and Hats

Frank sinatra in convertible wearing hat.

Building the Courage to Start Wearing a Hat – I won’t say that every man should have a hat in his wardrobe; however, I do think every man should strongly consider one, especially if it can practically serve him.  Do you live in rainy Seattle?  Consider a hat that will compliment your raincoat.  Spending hours outside in the hot Tucson sun?  Look for a lightweight and breathable hat that will shave 20 degrees off your day.  Remember function first, style second……but don’t forget about style, as you want a hat that you love to wear.

Three reasons to consider wearing a hat –

  1. Hats are useful – The right hat protects a man from the elements and enhances the way he interacts with the world.  They can keep the rain off your head, protect your chrome dome from the sun’s rays, and save a bad (or no) hair day. And amongst clothing and accessories, they are unique in their ability to communicate and convey respect for others. Tipping your hat to a lady or doffing it at a graveside service adds dignity to your comportment.
  2. A hat instantly sets you apart – Wearing a hat such as a fedora is rare these days, especially when worn properly and with confidence.  Although I don’t advocate setting yourself apart by simply being “the hat guy,” if used correctly it can be a distinguishing feature that helps cement your place in a casual acquaintance’s memory bank.  In the words of the great Las Vegas designer Nudie Cohen “Better to be looked over than overlooked.”
  3. Hats increase your perceived height – Hats create the illusion of added height; in one study men who wore hats were on average granted an extra two and one half inches by observers asked to guess their height. Why is this important?  Because height commands respect and authority in a first encounter.  Just ask any tall man who is used to being the first person people see when he enters a crowded room or on the other extreme a short man who can often feel overlooked.

More information about hat types, where to buy, and men to contact for detailed discussions:

Two AOM classics – Bringing Back the Hat and The Perfect Hat for Your Face

Our old friend the Houndstooth Kid weighs in – The Fedora at a Glance & What About Hats

Finally, two great forum/lounge sites to discuss the intricacies of wearing hats with other men:
The Fedora Chronicles & The Fedora Lounge

Brown fedora men's hat.

Drop the Baseball Cap – Wear a Real Hat!

Basic Hat Etiquette – A hat can be worn outdoors at athletic events, while riding public transportation and while in the lobbies and elevators of public buildings. Take the hat off when you enter a home, during a meal, at work (assuming you are indoors), when indoors and conversation is expected, and when you wish to show reverence (for example when meeting a religious leader or the playing of a national anthem). The key point to remember is that it covers part of the head and this can make you seem “aloof” and “distant;” understanding this, you can judge the situation and make the decision to wear the hat or take it off anywhere.

Male Jewelry – Watches, Rings, Cufflinks, and Bracelets

I’ll address each of these separately –

Timepieces : A Man’s Watch-It has been argued that with all the electronic gadgets we surround ourselves with, the man’s watch as an accessory is becoming antiquated.  I’m not going to take a stance either way, but as of 2010 a timepiece worn on the wrist is still a classic accessory.  If a man enjoys wearing a watch, he should have at least two in his wardrobe – one for sport and one for more formal occasions.  The general rule is the more simple the watch, the more versatile and formal it is.  Digital watches with plastic bands are for sport while large timepieces with multiple moving hands, gauges and metal bands are for the office.  The most formal watches are simple timepieces with a single set of hands and leather band.  If you’re attending a black tie event, forgo the watch altogether; the logic here is that a gentleman does not worry about time at galas such as these.

RingsWedding rings are always permissible to be worn.  Beyond that, rings are a matter of taste, and depending on your choice of ring and environment, they can symbolize membership, wealth, or in some people’s eyes, excess and extravagance.  Both school and fraternal rings are fairly common in the US, and rarely raise an eyebrow.  However, beyond two rings a man’s hands start to look adorned, especially if he has relatively small hands.  I wouldn’t wear more than two rings, preferably one on each hand.

Cufflinks – If a man owns a French cuff shirt he needs cufflinks and/or cuff knots.  The number you need depends more on how flashy your cufflinks are instead of how many shirts actually need them (although a general guideline is two sets for every shirt that requires them).  The logic here is that simple conservative cufflinks, such as plain silver or solid colored knots, draw little attention to themselves and create a positive but not deeply memorable impression.  A set of Elvis cufflinks on the other hand are going to be remembered and are therefore limited in how often they can be worn.  I advise you start your collection with simple, timeless designs; once you have three or so sets of links and perhaps 6 inexpensive knots, then you can introduce a few fun cufflinks.

Bracelets – Generally speaking, bracelets are a tricky area for men. In many cultures around the world they once symbolized power and position . But today a jeweled bracelet on a man is more of a fashion trend and not something I recommend for the average guy. As for “charity wristbands,” you should only wear a band for a cause you really believe in.


Your sunglasses should be clean and compliment both your face and the situation you’ll be wearing them in.  I recommend that a man have at least two pairs of sunglasses in his wardrobe – a classic, quality pair for every day use that can be worn with either a suit or polo shirt and a cheaper, disposable pair that can be worn in situations where the likelihood of them never being seen again is high (boating on Lake Travis).   If you are active in outdoor sports, you’ll at some point want to consider a pair of athletic wrap-around sunglasses.  However, understand these sport sunglasses should not be worn with business attire.

Classic sunglasses volcano sport, Wayfarer Aviator.

Volcano Sport, Wayfarer & Aviator Sunglasses

Good quality sunglasses are not cheap – in fact it took me a decade of putting up with bad eyewear before I finally bought a pair of Maui Jims.  However, like with most things, once you buy quality you’ll find it lasts longer, especially when you take better care of it.  Purchase a protective case and use non-scratch pads for cleaning the lenses.  I used to go through 2 or 3 cheap pairs of sunglasses a year – it’s now year 5 for my Ka’Anapalis and they only have one very minor scratch and look as great as they did when I first purchased them.  Quick note – know what you want when it comes to shades, and always be looking for clearance deals.  They can be found!

Tie Bars, Tie Chains, and Tie Tacks

The tie bar and its cousins are a great example of an accessory that serves a purpose – it keeps your tie from flying over your shoulder on a windy street and from falling into your food at a meal.  Tie bars also can add a bit of pizzazz to an otherwise dull ensemble and a simple stripe of gold, silver, or some other metal is always acceptable. I prefer to wear a tie clip at an angle to counteract the rigidity they connote. Other variations include the tie chain, which works in much the same manner, but instead of a fixed bar holding your tie in place, you have a drooping chain. The least favorable variant is the tie tack, as that it requires poking a hole in the tie which can damage a silk.  I do not recommend the tie tack unless you are wearing it with a knitted woolen tie.  If you own more than a few ties and wear a tie daily, throwing in a couple tie clips is a great way to add flavor to your suit, shirt, and tie.

The Pocket Square

A tastefully folded pocket square placed in the suit jacket’s breast pocket can lend some color and panache to an otherwise boring navy suit. For the first three suits a man owns, he should have three pocket squares for each, the first two being a solid cotton and silk white.  Past that, it’s a matter of taste and personality.  As we’ve written entire articles about this already, I’ll simply point to an Introduction to Pocket Squares and How to Fold a Pocket Square for more information.

Wallets and Money Clips

Which wallet you choose depends on your needs.  If you’re a frequent traveler, a billfold that is large enough for a passport, pen, and various other incidentals is handy.  A slim billfold that fits in the back pocket, however, is more suited for daily use.  Just remember that if you have the space, you’ll fill it.  Therefore the best way to avoid walking around with two inches of backside bulge is to own a wallet that doesn’t tolerate that type of expansion.

Leather wallet comparison sleeve passport Billfold Clamshell co.

3 different wallet sizes found over at Saddleback Leather Co.

Money clips are a great alternative to carrying a billfold; they fit naturally in the front pocket (a more secure area) and force you to trim down what you carry.  In doing so, a money clip helps eliminate the danger of carrying all your eggs in one basket – when a pickpocket strikes you’ve lost a little bit of cash vs. your social security card and a half dozen credit cards.

Briefcases, Notebook Cases, and Handbags

I recommend you have at least one simple dark colored briefcase in your wardrobe. Leather is a classic choice, and black or dark brown are safe colors.  If you are a professional who frequently travels for business, you should strongly consider owning two briefcases, a small one for daily use and another larger one that can hold a week’s worth of paperwork and your laptop computer.  In levels of formality, dark colors and a simple build are more formal than light colors and bags with all types of straps and pockets.

Classic briefcases hard case soft back backpack.

The case on the bottom left is casual – the case on the top left is more formal

The Boutonnière

A flower is the simplest, least used, and in my opinion most perfect accessory a man can add to compliment his clothing. It requires strength to wear, its life is short, it has a storied history, and on a spring day it can be found for free.  A boutonnière is properly worn on the left breast, near the heart, and keeping it simple and subtle is the key to pulling it off.

Final Note on Accessories

Accessories are like the service and ambiance surrounding a fine meal – they add to and enrich the experience.  The finest accessories in the world cannot help a man who doesn’t care about his appearance; however, the proper use of them can transform a decently dressed fellow into an extraordinarily dressed gentleman.

What to Look Forward to in Part IV

Yes, there will be a Part IV!  We’ll cover wardrobe storage and protection.  The worst thing you can do is spend money on quality menswear only to have it eaten by moths or not ready for service when you need it most.  See you in the comments!
How to Build Your Wardrobe: Part I 
How to Build Your Wardrobe: Part II – Men’s Clothing Specifics
How to Build Your Wardrobe: Part III – Men’s Hats, Watches, and Other Accessories
How to Build Your Wardrobe: Part IV – Protecting, Storing, and Cleaning Your Clothing

Written by
Antonio Centeno
President, A Tailored Suit
Articles on Mens Suits, Dress Shirts, Sport Jackets, and Overcoats
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