A Man’s Guide to Wearing Hats

This is a guest post written by Style Crew member, Eric Rodriguez.

When we think of hats, many of us, especially those in my age bracket, think of Cary Grant and Indiana Jones in their famous fedoras, Michael Corleone from “The Godfather” in his stylish Homburg and, most recently, Thomas Shelby from “Peaky Blinders” in his newsboy cap.  Hats were very commonplace in the late 19th Century to the end of the 1920s. But sadly, nowadays hats are rarely seen (with the exception of a baseball cap).

That being said, of all the accessories a man can wear, a hat is by far the most stylish.  A hat adds a touch of mystery, class, and sophistication to any outfit. It’s also a very suave way to finish off an outfit.  Here are my three favorite hat styles and how I wear them.

Fedora & Trilby

The word fedora comes from an 1882 play where the heroine wore a center creased, soft brimmed hat.  After Prince Edward started wearing them in 1924, it became popular for its stylishness and its ability to protect the wearer’s head from the wind and weather.  In 1920, it was associated with Prohibition and gangsters. In the 1940s and 1950s, noir films popularized it even more. It wasn’t until the late 1950s when informal attire became widespread that the fedora became less commonplace.

The fedora, with its lengthwise crease down the crown and its ‘pinch’ on either side of the front, comes in various felt fabrics such as beaver, rabbit, wool, and straw (aka Panama, which is worn primarily in warmer climates). It also comes in various crown and brim sizes.  It can be worn with the brim down for a classic, traditional look or the brim up for a more modern, youthful look. The classic look works best with more formal attire such as a suit or sports jacket. The more modern, turned-up brim, works well with jeans, khakis, and boots.  Personally, I think it gives off that rock and roll vibe.  In warmer weather, a Panama hat is the best option.  It works great with a summer suit or linen pants and a polo shirt.  My favorite fedoras are the Stratoliner and Whippet.

Like the fedora, the trilby also has its roots in the theater.  The hat was first popularized in a stage adaptation of George du Maurier’s novel “Trilby”. It was initially worn as a “rich man’s” hat in the early part of the 20th century and mostly only in Britain.  The hat all but disappeared and didn’t resurface until the late 70s as part of the retro scene and then disappeared again. The trilby is best known as the hat of choice by “Old Blue Eyes” Frank Sinatra.  The trilby, sometimes referred to as a “stingy brim”, is similar to the fedora, but it has a smaller crown and brim.

Cowboy/Western Hat

If there’s one hat that is considered the most recognizable throughout the world it’s the cowboy hat.  Recognized for its high crown and wide brim it is the defining piece of the North American cowboy. The first cowboy hat was designed by John B. Stetson in 1865 and was made popular by movie icons like John Wayne and Clint Eastwood.  Nowadays everyone from cowpunchers to rock stars wears a cowboy hat. Unlike other hat styles, a cowboy hat takes a bit more confidence to wear especially if you live in a place like New York City where cowboys aren’t as common. One of my favorite—and most complimented—cowboy hat to wear is the classic Open Road.  With its three indentations in its high crown, it gives an air of class and business.

Newsboy Hat/Flat Cap

The newsboy cap gets its name from its wide popularity with newsboys or “newsies”.  Although it’s thought of as a boy’s cap, it was popular with men of all ages during the late 19th and early 20th centuries.  Extremely popular with the working class, it wasn’t limited to them. The upper class often wore them to more leisure activities such as golf or driving.  The newsboy cap, also referred to as a Gatsby, paperboy, or applejack (as the wider, more floppy version is known as) is typically a 6 or 8 paneled cap with a front peak often made of wool or leather and lighter materials such as linen or cotton for warmer weather.  The flat cap, sometimes known as a scally, is a rounded cap with a small stiff brim.  Although these two styles of caps are often confused, the main distinction is that the newsboy cap is baggier and floppier than the flat cap.

Purchasing a Hat

If you’re purchasing your first hat it’s always best to skip the mall and department store and go to a quality hatmaker/dealer.  These are the people who really know hats and can explain the difference between a quality $200 beaver felt fur fedora and a $20 wool-blend fedora.  My first hat was a beaver felt Homburg which cost me $250. I instantly fell in love with the hat but wasn’t sure about the price. Once I was able to see and feel the differences between a quality hat and a cheap hat I was able to understand the reason for the price tag.   Now I’m not suggesting that your first hat should cost you $200, but it’s always best to know and see the differences. A quality fur felt hat will retain its shape and color over time. Specialists, like Stetson, Borsalino and Akubra for example, focus on quality and design and not on trends.

Choosing a Style and Color

When choosing a hat style think of what your personal style is and what you want the hat to say.  Since a fedora or cowboy hat is not something everyone is wearing it will get attention. For example, walk down the street in an Open Road hat and you will be noticed.  A newsboy or flat cap is probably the easiest choice to ease yourself into wearing a hat.  Its casual and unassuming style is easy to pull off and not as “attention-grabbing” as a fedora or cowboy hat.  Color and texture are just as important. A neutral color like tan, brown or grey is the easiest to style with your outfits.  Unless you’re looking for that “stand out piece, I’d avoid colors like red, yellow and multi-colors as well as large patterns.

So if you’re looking for something to add to your wardrobe that will make you stand out from the rest, give a hat a try.

Eric Rodriguez is a content creator based out of Brooklyn, NY focused on men’s style. He enjoys food, watches and fashion and is an up-and-coming model, having been featured in several campaigns for various brands. Currently, he is an ambassador for Ash & Erie as well as Beckett Simonon, the shoe company. 

You can check out his page here: @ericrnycstyle

Ivan Martinez

01. What do you do for work?

I work as a data analyst. I love to be able to discover something that can make a process more efficient and help the the company save money.

02. Who is your biggest style inspiration?

David Gandy. His style is classic and a classy guy overall. He’s able to look good in anything.

03. How do you relax?

I love hanging out with my daughter. She’s 1-year-old now, and my favorite part is being able to teach her about life.

04. What’s your #1 piece of fashion adavice?

Make sure that it fits!

05. What’s an underrated wardrobe piece that you love to wear?

My Nike Air Force 1’s. I’ve worn them since middle school and have loved the style ever since.

06. What wardrobe piece in your collection was worth the splurge?

My suede leather jacket.

07. What’s your favorite color to style?

Green. It’s an underrated color in menswear.

08. What’s your favorite occasion to dress up for?

I just always dress up.

09. What’s a fashion mistake every man makes?

Their pants are either too long or too short.

10. What’s a funny style story you have?

I styled myself for my 6th grade graduation, and I refused my moms assistance. I ended up wearing a Trunks Dragon Ball Z shirt. I still looked good though!

Ivan Martinez is a men’s lifestyle and style blogger based out of Minneapolis, MN. Ivan’s personal style is focused on highlighting classic, timeless pieces and adding in a twist of modern fashion.

Check out his page here: @iammrmartinez

Kian Concepcion

01. What do you do for work?

I work front office at La Puente High School by day and also work at an Amazon delivery station by night. Having two jobs means I get to influence more colleagues to dress better. I’m proud to say that some students at the high I school work at also draw inspiration from my content.

02. Who is your biggest style inspiration?

Alex Costa! The guy is literally a style god.

03. How do you relax?

I read books and watch my YouTube subscriptions.

04. What’s your #1 piece of fashion advice? 

Experimentation is key to unlock your personal style! Be sure to try items one at a time only. When a guy tries lots of things all at the same time, he may feel overwhelmed and that could stop him from further experimentation.

05. What’s an underrated wardrobe piece that you love to wear?

Any piece that is burgundy! Most guys can pull off this color.

06. What wardrobe piece in your collection was worth the splurge?

My brown leather jacket that I bought in late 2016. It’s made out of lambskin leather. I’ve had hundreds of wears with that jacket and it’s a compliment-getter!

07. What’s your favorite color to style? 

Blue. Blue is such a classic, versatile color and is pleasing to the eyes. Depending on the shade, blue can make you appear professional (navy), edgy (midnight blue), or fun to be with (sky or turquoise blue).

08. What’s your favorite occasion to dress up for? 

I have to go with weddings! My overall style is much more casual now. I still like to dress up with a nice suit though, and weddings allow me to do that.

09. What’s a fashion mistake every man makes?

People think that simply wearing big brands will instantly elevate their style. They only pay attention to the brand and forget everything else: the fit, the design, versatility, how they feel wearing an item, etc. A lot of factors come into play and relying solely on a brand’s name doesn’t automatically make you stylish.

10. What’s a funny style story you have? 

When I bought my first blazer, I did not remove the stitching at the vents. I thought it was part of the styling! I only used it once (I think haha) in public before I realized my mistake.

Follow Kian here: @elevatestyle_

A Guide to Shoes

This is a guest post by Kian Concepcion, a Style Crew member. 

“Button-up shirt? Check. Leather jacket? Got it. Black jeans? Yep. Hmm, now what shoes should I wear?”

Shoes can make or break your look. You can have a great outfit, some eye-catching accessories, and a nice fragrance to top it off, but if you end up with the wrong pair of shoes, your outfit will detract rather than attract people. That is why it is highly important to invest in your footwear.

At times, it can be confusing which shoes you should pick for a certain occasion. However, there really is no need to stress about it! In this simple guide, I go over 6 essential shoes you need to have in your closet that will cover any life situation you face, from formal events to days where you’re just relaxing.

There are two types of shoes to own: dress and casual.

Dress Shoes

Dress shoes are primarily paired with formal and dressy outfits. Think suits, tuxedos, dress shirts, and other formal/dress items. It’s notable to remember that the less details or decoration the shoes have, the more formal the shoe is.

Black Dress Shoes

Having black shoes in your closet is as essential as wearing your seatbelt while driving. This will be your most formal pair of shoes. Wear black shoes to important events such as weddings, funerals, black tie, and other formal occasions. You can also wear them to date nights when bringing your significant other to fancy restaurants that have a formal dress code.

Brown Dress Shoes

Brown dress shoes are less formal than black ones. They can be worn to the office, to personal events, and less formal occasions. Wear brown dress shoes to pair with your light-colored clothes such as khaki or beige pants, white trousers, etc. They also pair well with navy suits.

Double Monk Strap Shoes

Consider the double monk strap as your hybrid dress shoe. To get the most versatility out of it, opt for an oxblood or dark brown color. Double monks are incredibly versatile. You can dress them up with a suit or with a dress shirt and trousers. You can also dress them down with jeans and a casual button-up shirt.

Pro tip: In order to maintain the shape of your dress shoes, it is highly recommended you buy shoe trees. Shoe trees will help extend the life of your dress shoes since they prevent your shoes from developing creases.

Casual Shoes

White sneakers

No man’s closet will be complete without a pair of white sneakers. This will be your most versatile casual pair of shoes because it works with anything and everything. Wear them with jeans, chinos, shirts, button-ups, and yes, even suits – but only if you’re into that. Since dirt and stains will easily show up on white sneakers, it’s highly practical to buy white leather sneakers so you can clean them easily.

Athletic sneakers

For running errands and everything in between, a pair of athletic sneakers has your back (or feet in this case!). Feel free to choose which color and style you want and inject some of your personality in this look.


A dark brown pair of lace-up boots will give you the most bang for your buck. Boots protect your feet from the elements like snow, rain, and mud. They give any outfit a masculine vibe, so they’re perfect to wear on dates. Also, an added benefit to wearing boots is they can give you an extra inch in height. 

Wait, are you telling me I only need 6 pairs of shoes?

Treat this guide as having the bare essentials when it comes to shoes. Depending on your lifestyle and career, the types of shoes you purchase for your closet will vary. The shoes mentioned here will get you the most versatility because it covers every life situation or occasion that comes your way.

The next shoes you buy will be up to you. Do you mostly work with executives and high-level people? Then fill your closet with dress shoes.  Into running? Buy a pair of athletic shoes that will properly support your feet. Being fully aware of your personality and hobbies will help you purchase the right type of shoes.

Kian Concepcion is an Ash & Erie Style Crew contributor. Follow him on Instagram: @elevatestyle_

Gus Constantellis

Comedian, Writer, Lady Gaga fanatic. All accurate descriptors of Gus Constantellis. As a headlining comedian for the famed Broadway Comedy Club, Gus faces a unique dilemma in life.

He’s too funny. It’s becoming a problem for him in every aspect of his life. In fact, someone recently told me that they had to get rib surgery* because of Gus’ jokes.

That’s when we knew we had to recruit him to our Style Crew program. We thought, “If a short dude is funny enough to cause someone to get a “broken rib from laughing” diagnosis,” then he’s someone we need to get to know.

We recently caught up with the master rib-breaker himself to talk work, influences, and inspiration. Enjoy.

01. How would you describe what you do?

I’m a stand-up comedian/TV writer.

02. What’s your favorite joke/show you’ve written/done?

My favorite show I’ve ever done was headlining Broadway Comedy Club last October. My favorite jokes are the ones about my mom because they always connect with the audience the most. 

03. Who would be your dream collaboration? 

Dream collaboration would be Lady Gaga. I don’t know why we would ever collaborate but it would be an absolute dream to work with her on something.

04. Who is your biggest style inspiration?

Christine and the Queens – a French pop singer. She keeps it classic and simple. She dresses gender neutral and she has a really cool look that’s sleek at the same time.

05. How do you relax?

Watching reality competition shows. Favorite is RuPaul’s Drag Race.

06. What’s your #1 piece of fashion advice?

Wear clothes that fit well and you’ll instantly elevate your look.

07. What’s an underrated wardrobe piece that you love to wear?


08. What wardrobe piece in your collection was worth the splurge?

A perfectly fitted navy blazer.

09. What’s your favorite color to style?

Navy blue.

10. What’s your favorite occasion to dress up for?


11. What’s a fashion mistake every man makes?

They wear terrible shoes or socks to go with a great outfit. 

12. What’s a funny style story you have?

One time,  I bent down and accidentally ripped my chinos. It was so embarrassing because it was at the beginning of a long day and I had no choice but to roam around with ripped chinos until I got home.

You can keep up with Gus on his Instagram (@constantlygus) or his Twitter (@constantlygus).

*You don’t think he really broke someone’s ribs, right?!