The History of Baseball Caps & How to Style Chic Baseball Cap Outfits

Lena Davydova
by Lena Davydova

In this style guide, I’m going to show you some baseball cap outfits that I’ve put together. Baseball hats are an accessory that, let’s be real, are never going to go out of fashion, and I think that most of us have one or two of them in our closets. Let's get started!

The history of baseball caps

The history of baseball caps

The very first baseball hats were worn in New York back in 1949 and they were made of straw. This was because, until 1954, baseball players could pick any kind of hat they wanted, just to keep the sun out of their eyes, and that’s where the baseball cap trend started. 

Vintage baseball caps

The cap as we know it today began to take shape around the turn of the last century. Back then, they were solely worn by professional baseball players, and while the look of baseball caps hasn’t changed significantly since the 1950s, the ways of styling it has. 

Baseball caps in popular culture

With the help of TV and music videos, the baseball cap made its transition from the sports field to street fashion. 

Baseball caps in high fashion

Nowadays, it can be worn as a fashion statement itself. All major fashion houses have baseball caps in their collection.

Baseball caps in the Celine fashion show spring/summer 2021

The most memorable moment for the baseball caps in 2021 was the spring/summer Celine fashion show. The show for sure made a big impact on the growing popularity of this trend.

How to style baseball cap outfits

So let’s see how we can fit baseball caps into our everyday casual and chic outfits.

Edgy and feminine baseball cap outfit

1. Edgy and feminine

The first outfit is pretty feminine but edgy at the same time. I’m wearing a skirt, and I’ve accentuated my waist by belting it. I also have a lot of structure in the blazer, and I’m wearing chunky boots on my feet.

The baseball cap and fanny pack are cute little accessories that bring the outfit together and add some interest.

Casual baseball cap outfit ideas

2. Loose leather

In the next outfit, I’m wearing a structured oversized blazer that contrasts against the loose-fitted leather pants, t-shirt, and sneakers.

This is an outfit that I would wear when I want to be put together but still comfy. The addition of the green baseball cap here makes it look less formal.

Outfits to wear with baseball caps

3. Sporty elevated

The next outfit starts off feeling a little bit sporty with sweatpants, sweatshirt, baseball cap, and sneakers.

I’ve added a classic element into the mix with a trench coat. The trench coat elevates the outfit and makes it a bit more feminine.

How to style a baseball cap with jeans

4. Classic denim

The next outfit is a classic combination of blue jeans and a leather jacket. I’ve added some heeled ankle boots with a square toe for a stylish shoe choice.

The baseball cap is the perfect finishing addition to this look and adds a fresh pop of color.

How to style a baseball cap with a suit

5. Well suited

I couldn’t create this style guide and not include a classic suit in the mix. Adding a baseball hat to the suit once again just makes it less formal.

I also picked out a lime green bag which complements the color of the baseball cap and helps to spice up the black monochrome look.

Layered baseball cap outfit

6. Layered to perfection

Here, I’m wearing a white button-up over a black turtleneck. I then layered a long wool coat over the top. The overall aesthetic is classy and minimalist.

The baseball hat in a bright and trending color helps make the outfit more interesting.

How to wear a baseball cap with an oversized hoodie

7. Oversized hoodie

In this outfit, I’m wearing an oversized hoodie with jeans. To contrast these casual pieces, I’ve added in some feminine heels and a patent leather clutch bag.

This is a really good example of how you can easily dress up your favorite hoodie.

Wearing a baseball cap with the "skirt over pants" trend

8. Skirt over pants

For the next outfit, I’m trying out the latest skirt-over-pants trend. It is out of the ordinary, but I quite like it. What do you think?

How to wear a baseball cap

9. Silky and stylish

For the last baseball cap outfit idea, I wanted to style a silk slip dress. I decided to pair it with a trench coat and my chunky boots.

I also added a feminine bag, and since the baseball hat is green, I thought it would be nice to include another green pop of color in the outfit. I went with a pair of green socks that stick out of the boots; they’re quite subtle but are a nice finishing touch.

Styling baseball cap outfits

So there we have a quick roundup of the fashion history of baseball caps - where they came from and how they go to where they are today, as well as how to style baseball cap outfits for the current season.

There are so many different ways you can style a baseball cap; I hope that my outfits gave you some inspiration!

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