How to Style a Flat Cap or Newsboy for Ladies

How to Style a Flat Cap or Newsboy for Ladies

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I planned this post to be something entirely different from what you’re about to read. I’d planned on some broad unisex style tips like how to mix patterns and textures, how to wear caps with suits or dresses (yes to both, btw), and some cap style names (you can find our complete guide to cap names here). After a rather dull scroll through Pinterest, I decided to look through the hundreds of photos in our Customer Portrait Day archive to find inspiration and illustrations of my points for this post.

What is Customer Portrait Day?

Behind the scenes at Customer Portrait Day Summer 2023

We've been hosting Customer Portrait Day twice a year since 2018 (with the necessary safety breaks in 2020 and 2021 for the pandemic). Our incredible house photographer and long-time customer Aaron Paschal of AP2Photography brings his cameras and soft encouragement. Everyone always looks gorgeous - Aaron has a real gift for putting people at ease and capturing their humanity (check out his other projects including his Mortal Man photo essay and his recent work on Instagram sharing everyday moments in Dayton). On Customer Portrait Day, Aaron walks around our neighborhood with whoever shows up to have their photo taken. We never know who’s coming or what they’ll wear. We don’t style or stage anyone or anything. And all of the photos of people on our website and our social media come from these sessions. I find inspiration over and over again from both the photos and the real life people, so when I felt stuck with cap styling I went to the archive.

Going completely off script

I started by making a copy of any photo of someone in a cap and downloading them all to my desktop. Then I started organizing them into gendered categories then grouping photos of the people who show up season after season in caps. You know who showed up season after season in a cap? Women. As I  was looking at these photos spread out on my desktop, I was genuinely surprised because we sell overwhelmingly more caps to men, especially through our online store. Moreover, at least once a week I have a conversation with a woman who comes in the store looking for something casual and gets antsy when I suggest a cap because she perceives caps as too masculine for her to wear. There’s a surprising amount of disbelief that women can wear caps, even as I myself am often wearing a cap while talking to said woman – I get a lot of “it works with your style but it’s not for me.”

And so here we are. I find myself thinking about women’s hang ups around caps and wanting to give some advice on how to wear them.

Pinterest's suggestion for womens flat cap outfits are boring

One of the things I realized right away was that the kinds of outfits my female customers opt for with caps are almost completely unrelated to the kinds of women’s cap outfits I saw on Pinterest. On Pinterest, I kept getting pictures of very thin and very young women wearing feminized menswear, often a complete suit with a vest, which is great if you’re really into head to toe tweed and, well, suits, but for our average customer who’s looking for something to run to the grocery in when she hasn’t done her hair,  it’s completely irrelevant. I was really struck by the lack of creativity in the fashion industry (full transparency, I almost always am). In comparison, my female customers slay on a day to day basis.

We’re going to look at three series of photos with my customer Billi. Billi, btw, is a 10 year brain tumor survivor and possibly the biggest ray of sunshine I’ve ever met. She brings so much joy and determination to everything she does, including her project Billi’s BElievers through which she offers hope and inspiration for people living with brain tumors. I always feel invigorated when I run into her out and about in Dayton and today she brought me inspiration on caps and femininity.

Photo series of a woman in a plaid flat cap, black top, and tulle tea skirt

Be feminine

I love this series of photos of Billi from 2019. She’s wearing a traditional windowpane plaid flat cap with a beautiful, soft blush tea skirt and fitted black leotard top. She does a wonderful job mixing textures. These photos tell a story of a beautiful woman who loves herself. She brought that rose with her from home (like I said, we don’t style or stage - Portrait Day is our people being themselves). I don’t think anyone could look at these pictures and think Billi looks anything but deeply feminine and beautiful. It’s the color combination that really does it. She could have opted for black pants or a long black skirt and looked great. The blush tulle softens everything and pulls out the lines of color mixed into the plaid, making the hat itself more interesting.

Mixing and matching

Woman in a denim summer dress, cowboy boots, and plaid flat cap

This series of Billi is from the summer of 2023. I love how cute she is in her denim dress and cowboy boots. There was one summer when I was a kid where I only wore cowboy boots every day all day. I’m sure I drove my parents crazy getting them muddy and filled with sticks and stones and what all have you (I grew up on a small farm where my siblings and I spent our summers outside, mostly climbed trees and played in a giant pile of dirt and built hay forts in the barn). I love an outfit that contrasts masculine and feminine fashion elements, which gives me a real soft spot for cowboy boots with dresses. Dresses and boots are one of the easiest ways to do contrast softness and hardness (I might also be proving that I was a teenager in the 1990s who wore combat boots with everything). She’s also playing a bit with high-low fashion with her workaday not-the-kind-you-wear-to-your-niece’s-quinceanera cowboy boots and the kind of preppy plaid ivy cap that could be found on a golf course in Nantucket. This outfit is not as soft as her 2019 look but it’s overwhelmingly fun and breezy and very feminine.

Woman in denim shorts, cream sweatshirt, and patchwork newsboy cap

Be Sporty

This final series from this past fall, 2024, is casual and sporty. Billi is again playing with textures mixing denim with a cozy sweatshirt and patchwork cap. You could do a similar look with a plaid or solid cap but the patchwork adds a lot of interest. We’re big believers in patchwork caps at Brim. Why? Because they’re quite possibly the most versatile cap you can possibly have. They go with so many things thanks to all the colors and textures and they’re traditional but far from dull. Patchwork caps liven up even the most boring outfit. You know what makes this outfit feminine? Billi.

So, ladies, you too can wear a cap and 100% definitely not be mistaken for a man. You can be as girly as you want in a newsboy or flat cap. And unlike most hats made specifically for the women’s market, caps come sized. Big head? Little head? We got you. We currently have 166 unique color/pattern combinations in stock, in most cases in five sizes - to say that color and pattern combinations are infinite is just shy of an exaggeration.

Questions? As ever, hit us up.

SHOP FLAT CAPS & NEWSBOYS 

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