Normally, we rush back into the house if we forget our mobile phones or car keys, but can you picture a man dashing through the front door to pick up one of his favorite hats to wear with suits? Well, I have seen such a man in the White Collar series — Neal Caffrey, a woman charmer, knew the hat completed his lady-killer looks.

Once you see how effective it is, you will know that hats worn with suits are the way to a woman’s heart. Still, you need to get it right for it to work its magic. So, here’s the ultimate guide on how to wear hats with suits and other menswear looks.

Not All Hats Go With Suits

Before you think you will get a hat to wear with every suit in your closet, here is the deal breaker — not every hat works with this kind of clothing. Let’s take a look at a few factors to consider when looking for matching men’s suits with hats.

Color

It is a well-known fact that most of us believe that black goes with everything. Others, however, would caution us to be careful when picking a colored hat to go with a black suit because a brown or dark tan hat does not complement it. Nevertheless, a brown or black fedora will do when reaching for the classic look. You can also break that dull look of a neutral suit with a pop of color rendered by a pink fedora.

Black suits match great with slightly brown, light grey, beige, or white hats. A beige, orange, yellow, light brown, white, or dark brown hat will complement navy blue suits. Dark grey suits go well with the same colors as the navy-blue suits except for orange and yellow. Lastly, if you have a neon-colored hat you have been stashing in your closet and are wondering what would work well with it, it is time to pull it off with a light grey suit.

At the end of the day, it all boils down to your personal preference and taste. But in a world where everyone abuses freedom, basic guidelines help instill some objectivity in our dressing, at least for the sake of us who constantly look at you. It, therefore, helps to remember that no color goes with everything with every suit in the closet. So whenever you stand in front of the mirror with your suit and hat on and doubt that you look good, you probably do not.

Style

The head shape is among the many factors to consider when choosing a hat; while some work best with small facial features, others will go perfectly for those with more pronounced facial characteristics. Oval face shapes are lucky since they can wear almost every type of hat, but if yours is longer than average, ditch the close-fitting crowned hats and opt for the wider ones.

As for round face shapes, you want to add a bit of imbalance by using hats with some angular outline. Square shapes should also create asymmetry by having hats tipped to one side. Finally, wearing brimmed hats requires heart and diamond face shapes to add volume to the upper face.

Occasion

Men in suits and hats can be eye candy even in offices, especially if they know how to pair the two types of clothing well. You can easily upgrade your formal look with a simple item of clothing, like a flat cap. However, you have to pay attention to the weather, lest you mess up the look by wearing a hat made from the wrong material.

During winter, a warm flat cap made from wool will be ideal, whereas in summer, a hat made from lighter material will do better. A fedora also works well in summer or winter, but you must know which fabric to pick.

Another point to note about fedoras is that they go beyond the office and will have a classic appeal in a formal setting where you have to wear a tuxedo. So whether you’re attending your child’s graduation or looking forward to the father-daughter dance at her wedding, wear that fedora with confidence and complete that sophisticated look that tuxedos tend to ooze.

Fitting

It will not matter whether you choose the right color and style for hats to wear with suits if they do not fit your head well. An ill-fitting hat makes you look sloppy no matter how polished everything else is. You can avoid this grave fashion mistake by measuring your head size. All you need is a string to go around your head. The best place to measure is right above your eyebrows since that is where the hat sits.

Hat sizes depend on specific measurements. For instance, the small size is for a circumference between 53 and 55 inches, while an extra-large size is for 60 and 62 centimeters. Remember that if you happen to be between sizes, you would rather err on the larger size instead of choosing the smaller one.

Different Hats for Men in Suits

I have mentioned flat caps and fedoras, but do you know what I’m talking about, or are you still in the dark? Let me shed some light on the specific hats you should incorporate into your wardrobe if you love formal wear.

Trilby

Described as the hat for all occasions and a timeless classic that can be worn not only by men but also by women and children. Its name comes from an actress who played Trilby in the play Trilby, which is based on an 1894 novel of a similar title. The lady who played the lead character wore a short-brimmed hat with a sharp rear brim. Since then, the trilby hat has grown in popularity, and with good reason.

The trilby is one that you do not want to miss in your hat collection. Whether you want something to complement your black suit or a casual look, the trilby will always be there for you no matter the setting. It is the type of hat to wear when you have to go to the office and head to a party later.

For the person who is trying out hats for the first time, the trilby will lend the confidence to push the limits with other hat styles. Besides, whatever type of face shape you have, you can play around with the trilby by choosing one based on the width of the brim that suits your face.

Fedora

The fedora or snap-brim hat is a well-known classic made from felt. This hat is often 3 inches wide, measures around 5 inches high, and usually has an indented crown. The snap brim enables you to angle it to your preference, whether upwards or downwards. It may even have a decorative ribbon or fabric band whose width plays a huge role in how vintage the hat looks. The wider the band, the more vintage it appears and the classier you will look while wearing it.

Frank Sinatra helped to popularize this hat, and today, many accept it as a fashion statement despite some ignorantly referring to it as “antiquated.” If you feel it is too plain and deserves a bit of a lift, add a feather for that extra classy appeal.

If you feel bold enough, why not mix and match some textures? For instance, a cashmere suit will pop out with a velvet fedora, but only because both materials are smooth. So, you still have to be careful not to clash the textures. The mix and match can extend to colors, but only if they are of the same palette.

Flat Cap

The flat cap dates back to 1571, when British law mandated boys over six years old and non-noblemen to keep their heads covered during holidays and Sundays. Despite the abolishment of the law with its crazy hefty fees for non-compliance, men had become so accustomed to wearing this hat that they continued with the tradition until it became an integral part of their fashion. Lovers of the Peaky Blinders series will notice these were the hats worn by the main cast. Of course, you can copy the style, but not entirely — do not sew razors into the caps to blind anyone.

Since it is a classic, do not overwork it so that it doesn’t lose its appeal. Once you choose a pattern, stick with it and preferably go for natural materials. Do not choose a color that matches your suit; otherwise, the cap might not even make any complementary effort to your overall look.

Besides tweed suits, you can also wear them with an overcoat during winter. And just because I’m talking about men’s suits and hats, do not get confused and wear flat caps with all types of suits; you must never wear tracksuits with flat caps. However, one great thing about flat caps is that even after ditching the office look, you can still turn heads when you wear them with denim jackets, Henley shorts, and Chelsea boots.

Parting Shot

One thing you have to agree with is that men in hats look sexy. If you are in doubt, look at Ne-Yo and Pharrell and how fine they are with their respective preferences for hats. You just have to find the one that works best for you, and once you get it, there is no going back.

The hat for men is like a purse for women; they are a language that men speak, and you can never have too many. Once you get the hang of it, it becomes a survival kit that you can never leave home without. You even feel naked without it. Now that you know a few to get you started on the journey of choosing the right one to wear with your suits, why not buy a few and transform your look?