baker boy hat – how to add one to your look

How can you add instant style this season? Easy—just pop on a Baker Boy hat. We’ve fallen in love with this hat style for its timeless appeal and the way it adds flair to any look. So, how can you wear a Baker Boy hat to elevate all your outfits? Let’s take a look.

What is a baker boy hat?

Before we get onto how to wear one, what exactly do we mean by a baker boy hat? Well, rather than a flat cap, or a baseball cap, the baker boy cap is more rounded and elevated, giving it more height and shape. You can also look for newsboy, breton, fisherman and fiddler caps, which also have that very similar raised crown look.

Sylvia in a striped shirt and black pants | 40plusstyle.comSylvia in a striped shirt and black pants | 40plusstyle.com

similar shirt (another option here), wide pants, sneakers, hat, earrings and sunglasses

Why we love them

They are menswear inspired

Because baker boy hats take their inspiration from menswear, they immediately add a touch of the unexpected to your outfit.

They elevate simple outfits

You don’t have to think too much about the rest of your outfit because the hat adds style for you. Even if you’re wearing the simplest of looks like your favorite jeans and t-shirt, a baker boy hat instantly elevates your style and adds a talking point.

They’re a conversation starter

We bet you get lots of people telling you they like your hat. They’re a conversation starter and make you feel more confident.

You’re in good company

You’re also in great company when you wear a baker boy. While she isn’t quite in the 40+ bracket yet, we’ve spotted Blake Lively often wears a baker boy, as does Janelle Monae, and Katie Holmes.

Psyche in green coords | 40plusstyle.comPsyche in green coords | 40plusstyle.com

Psyche @economyofstyle above tops off her green co-ord outfit with a rattan baker boy hat, and matches her headwear to her sandals.

Recreate her outfit with this similar green coordinates, sandals, hat and belt.

The best baker boy hats in stores now

Let’s show you some examples of the most stylish baker boy hats you could choose in stores.

For a true classic, opt for a gray felt baker boy like the Isabel Marant cap (below).

Isabel Marant Evie Wool-Blend Newsboy Cap | 40plusstyle.comIsabel Marant Evie Wool-Blend Newsboy Cap | 40plusstyle.com

Isabel Marant Evie Wool-Blend Newsboy Cap

The Eugenia Kim cap (below) features a little bit of bling thanks to the chain detailing.

Green baker boy cap | 40plusstyle.comGreen baker boy cap | 40plusstyle.com

Eugenia Kim Sabrina Wool Newsboy Cap

If you have a glamorous style personality, then the sparkly baker boy (below) is for you. Keep the rest of your outfit pretty simple.

Ruslan Baginskiy Embellished Baker Boy Cap | 40plusstyle.comRuslan Baginskiy Embellished Baker Boy Cap | 40plusstyle.com

Ruslan Baginskiy Embellished Baker Boy Cap

Mixing black and white is always timeless and the monochrome cap (below) has done this for you. You might want to add this to one of your black and white outfits.

Ruslan Baginskiy Baker Boy Cap | 40plusstyle.comRuslan Baginskiy Baker Boy Cap | 40plusstyle.com

Ruslan Baginskiy Baker Boy Cap

You can wear baker boys for any season. Choosing a linen blend like the MANGO cap (below) can be a great way to wear your cap into the warmer months.

MANGO Linen-Blend Baker Boy Cap | 40plusstyle.comMANGO Linen-Blend Baker Boy Cap | 40plusstyle.com

MANGO Linen-Blend Baker Boy Cap

Add a pop of color to your outfits with the red cap (below).

CRAGGIHATS Berker Boy Hat | 40plusstyle.comCRAGGIHATS Berker Boy Hat | 40plusstyle.com

CRAGGIHATS Berker Boy Hat

A hat can also be a great way to add texture to your outfit like to cord cap (below) with button detail.

accsa Newsboy Cap | 40plusstyle.comaccsa Newsboy Cap | 40plusstyle.com

accsa Newsboy Cap

Checks are a fantastic print for a baker boy cap. We love the herringbone print on the hat below.

Comhats Merino Newsboy Hat | 40plusstyle.comComhats Merino Newsboy Hat | 40plusstyle.com

Comhats Merino Newsboy Hat

Or, opt for a bolder, more colorful check like the newsboy (below).

Hatful Memories Newboy Cap | 40plusstyle.comHatful Memories Newboy Cap | 40plusstyle.com

Hatful Memories Newsboy Cap

Another option with a chain for you now, this time in a stylish black print.

INOGIH Baker Boy Hat | 40plusstyle.comINOGIH Baker Boy Hat | 40plusstyle.com

INOGIH Baker Boy Hat

Outfit ideas for your baker boy hat

So, now that you’ve picked out your favorite baker boy, what should you wear it with? Let’s take a look.

With your favorite jeans

A great starting point for your outfit is to pick out your favorite pair of jeans, and your hat. Then, simply add a T-shirt or blouse and you’re good to go. Below, we’ve chosen to mix the masculine nature of the hat with a feminine blouse. For cohesion, we’ve matched the handbag color to the cap.

Jeans and baker boy outfit | 40plusstyle.comJeans and baker boy outfit | 40plusstyle.com

Alice + Olivia April Floral Blouson-Sleeve TopAlice + Olivia Missa Crystal Stripe Wide-Leg JeansLAUREN Ralph Lauren Leona Espadrille SandalsAimee Kestenberg Aura A-Line Shoulder BagKendra Scott Chandlier Huggie EarringsEugenia Kim Sabrina Wool Newsboy Cap

Eileen in a baker boy hat and striped sweater | 40plusstyle.comEileen in a baker boy hat and striped sweater | 40plusstyle.com

Eileen @eileenternullo above opts for a maritime inspired outfit with her cap and striped sweater.

Get her look with this similar sweater, jeans, sneakers, hat, earrings and sunglasses.

With cargo pants

Cargo pants are particularly on trend this season and go really well with baker boy hats. Wear with a camisole and denim jacket.

Cargo pants and denim jacket outfit | 40plusstyle.comCargo pants and denim jacket outfit | 40plusstyle.com

Ronny Kobo June Denim JacketTheory Animal-Print Jacquard TankAlice + Olivia Olympia Mr Baggy Cargo PantsFranco Sarto Diva Kitten Heel PumpsAimee Kestenberg Aura A-Line Shoulder BagLAUREN Ralph Lauren Tartan Hoop EarringsIsabel Marant Evie Wool-Blend Newsboy Cap

With sailor pants

Sailor pants are another great pairing for baker boy hats. Below, we’ve also added a sleeveless trench coat.

Trench coat and sailor pants outfit | 40plusstyle.comTrench coat and sailor pants outfit | 40plusstyle.com

J.Crew Étienne Oversized ShirtCOS Sleeveless Trench Coat (similar here) – Alice + Olivia Narin High-Rise Stretch Flare Crop JeansBzees Everly Strappy SandalsCole Haan Go Anywhere ToteShashi Hailey Drop EarringsHatful Memories Newboy Cap

with black pants and a graphic print top

Black pants are a classic that go with everything, including your baker boy caps. For added drama, wear with a graphic print sweater.

Graphic print top and black pants outfit | 40plusstyle.comGraphic print top and black pants outfit | 40plusstyle.com

Alice + Olivia Oscar Saceface Double Knit Pullover SweaterAlice + Olivia RMP Back Zip Bootcut PantsSöfft Carleigh Heeled SandalsMadewell Soft Grain ShopperLAUREN Ralph Lauren Tartan Hoop EarringsCRAGGIHATS Berker Boy Hat

Fonda wears a baker boy hat | 40plusstyle.comFonda wears a baker boy hat | 40plusstyle.com

Fonda @savvysouthernchic above keeps the rest of her outfit simple and elevates her style with her baker boy hat.

Steal her look with this similar sweater, jeans, boots, hat, earrings and necklace.

with Blazer dress and slim pants

For a glamorous evening look, wear your baker boy hat with a blazer dress and slim pants.

Baker boy hat and blazer outfit | 40plusstyle.comBaker boy hat and blazer outfit | 40plusstyle.com

Alice + Olivia Esther Embellished Cotton Blazer DressBOSS Slim-Fit Jeans in Comfort-Stretch DenimFranco Sarto Diva Kitten Heel PumpsCole Haan Go Anywhere ToteShashi Hailey Drop EarringsINOGIH Baker Boy Hat

with ruana

A great look for transitional weather, pair your baker boy with a ruana or poncho.

Ruana and baker boy hat outfit | 40plusstyle.comRuana and baker boy hat outfit | 40plusstyle.com

UGG Tasman RuanaMisook V-Neck Soft Knit Tank TopGood American Good Legs Crop Skinny JeansAnne Klein Suri Suede BootsMadewell Soft Grain ShopperCOS Organic-Shaped Pendant NecklaceComhats Merino Newsboy Hat

With a sleeveless dress and t-shirt

Do you have a sleeveless dress in your closet? Update it by wearing it layered with a t-shirt underneath, and top off with your cap.

Striped t-shirt and dress outfit | 40plusstyle.comStriped t-shirt and dress outfit | 40plusstyle.com

Theory Boxy Striped T-ShirtStaud Ellison Knit Pleated Midi-DressTory Burch Howell Court SneakersCole Haan Go Anywhere ToteKendra Scott Chandlier Huggie EarringsRuslan Baginskiy Baker Boy Cap

Sylvia in a sleeveless dress and baker boy hat | 40plusstyle.comSylvia in a sleeveless dress and baker boy hat | 40plusstyle.com

similar teedress (another option here), tightsbootsbag (another option here), earringshat and sunglasses

With maxi skirt

A maxi skirt is a great way to add drama to casual looks, and you can up the style stakes by adding a baker boy cap.

Maxi skirt and cable knit sweater | 40plusstyle.comMaxi skirt and cable knit sweater | 40plusstyle.com

Polo Ralph Lauren Julianna Cashmere Cable-Knit SweaterAlice + Olivia Rye Tweed Slit Maxi SkirtSöfft Carleigh Heeled SandalsMadewell Soft Grain ShopperLAUREN Ralph Lauren Tartan Hoop Earringsaccsa Newsboy Cap

with full skirt

For a preppy take on the baker boy trend, wear with a polo neck top and full skirt.

Polo neck top and full skirt | 40plusstyle.comPolo neck top and full skirt | 40plusstyle.com

J.Crew Vintage Rib Polo T-ShirtAlice + Olivia Earla Lace Midi-SkirtTory Burch Howell Court SneakersMadewell Soft Grain ShopperLAUREN Ralph Lauren Tartan Hoop EarringsMANGO Linen-Blend Baker Boy Cap

Your baker boy cap outfits together in one capsule

How to wear this season's trendiest hat: the baker boy hat | 40plusstyle.comHow to wear this season's trendiest hat: the baker boy hat | 40plusstyle.com

similar dress (other options here, here and here), sandals, hat, earrings, necklace, sunglasses, backpack

Below, you can see the outfits from above together in one capsule. You can see you can wear the clothes, shoes and accessories in different ways to create many more looks.

Baker boy hat outfits | 40plusstyle.comBaker boy hat outfits | 40plusstyle.com

shop the outfits and baker boy hats below:



Has this article inspired you to add a Baker Boy cap to your closet and your outfits? Or are you already wearing one? Let us know in the comments below.

Continue reading:

  1. 10 Essential Fashion Accessories Every Woman Should Own
  2. How To Wear A Hat – The Ultimate Guide
  3. The Best Shops On Etsy And Other Brands For Contemporary Jewelry

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How to wear this season's trendiest hat: the baker boy hat | 40plusstyle.comHow to wear this season's trendiest hat: the baker boy hat | 40plusstyle.com

SylviaSylvia


Sylvia is 40+style’s editor-in-chief and has been helping women find their unique style since 2011. An alumni of the School of Color and Design, she is devoted to empowering women of any age to look and feel their best. Read more about Sylvia and 40+style on this page.

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