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How to Wear a Beanie: 35 Ways Men Can Do it Right

If you’re thinking that beanies are a winter hat/accessory, you are wrong. Beanies are probably the most popular hipster turned fashion icon accessory trending right now. They are also very versatile because they make a statement when pairing it with any outfit– dressy or casual. They can literally go with every color, style, theme, you name it, you can make it work.

The beanie itself is a contrast item, if you are wearing black pants, with a black plaid shirt, you don’t have to wear a black beanie. Try a grey beanie instead and add some contrast, it helps break up the outfit. Also, texture matters when it comes to beanies. If you are doing a more rugged or casual look, pair it with more of a ribbed or waffle knit beanie. But, if you’re doing more of a dressy/sleek look, pair it with a tightly knit beanie. Pairing it accordingly can help make the outfit cohesive and keeps it from looking out of place.

Basically, if it’s cold outside there is no reason not to throw something on your head.  And if it’s Sunday afternoon and you haven’t showered, not a problem.  Of course, if you still aren’t sure how to match up a beanie with the rest of your look, check out the pages to follow and learn 37 to wear a beanie.

Harry Styles Beanie + Henley Look

Harry Styles Henley Beanie Look

Harry Styles is rocking his long hair with a beanie and wears it in the most popular way, accompanied by good ole’ Henley top. Get the look here: Black Beanie $8.50 / Charcoal Henley $50

Liam Hemsworth Hipster School Boy + Beanie Look

Liam Hemsworth Hipster School Boy Beanie Look

Here we see a beanie with short hair. The Hipster School Uniform look worn by Liam Hemsworth – amped up by his bold teal beanie and red kicks. Get the look here: Slim Fit Khaki Pants $17.80 / Light Blue Short Sleeve Shirt $20 / Teal Blue Beanie $40 / Red kicks $45

David Beckham Casual Rocker Beanie Look

David Beckham Rocker Beanie

David Beckham pairs his black beanie with a chambray shirt, and fitted black jeans. Casual rocker style.  Get the look here: Chambray Shirt $69 / Black Slim Jeans $89 / Boho Mens’ Bracelets $24 / Black Beanie $7.58

Channing Tatum Textured Beanie Look

Channing Tatum Texture Beanie Look

Channing Tatum shows us how grey and brown can look good together, if paired right.  It’s all about the differentiation in textures: linen shirt + wool sweater + tweed jacket, and of course that grey beanie, which brings the whole look to a much more casual level and allows even a dressed up tweed jacket to work in a dive bar.  Get the look here: Long Sleeve Grey Stripe Shirt $26 / Brown Sweater $60 / Grey Tweed Jacket $298 / Dark Worn Wash Jeans $98 / Grey Beanie $24

The Clean Cut, Rugged On The Side Beanie Look

clean rugged beanie look

This beanie look is all about that sex appeal. Ladies love that clean cut, but slightly rugged look. The jacket gives this appearance more of a dressier appeal, while keeping it fashion forward.  Get the look here: Wool Blazer $149 / Basic White Tank $3.80 / Grey Wash Pants $34 / Burgundy Beanie $4

Elegantly Rugged Beanie Look

elegantly rugged beanie look

There’s that dressy, but slightly rugged look the ladies love again. The beanie is the magic trick that pulls this outfit together. Get the look here: Navy Knit Blazer $42 / Blue Dress Shirt $92 / Brown belt $10 / Dark Slim Fit Jeans $43 / Grey Beanie $16

Enrique Iglesias Classic Bad Boy Beanie Look

Enrique - Bad Boy Beanie Look

Enrique Iglesias is the beanie swagger king. This man started it all. This look is classic Enrique. Also what we like to call the Classic Bad Boy Look. Get the look here: Lucky Brand Moto Jacket $399 / V-Neck White Tee $9.99 / Vintage Wash Jeans $71 / Charcoal Beanie $28

Plaid Swagger Beanie Look

Plaid Swagger Beanie Look

Plaid is always comforting to go-to on those days you just don’t know what the hell to wear. A moto jacket on top to bring out the ruggedness, a beanie, you have a sick outfit in your hands. Get the look here: Navy Plaid Shirt $29.50 / CK Brown Moto Jacket $89 / Brown Beanie $14

Ashton Kutcher Stripe on Stripe Beanie Look

Ashton Kutcher Striped Beanie Look

Ashton Kutcher is also one of the men that started the beanie fad for men. Here he shows that solid colors aren’t always cool. Striped blazer with striped beanie… two thumbs up! Get the look here: V-Neck Basic T-Shirt $26 / Striped Jacket $653 / Striped beanie $17

Surfer Hipster Beanie Look

Surfer Hipster Beanie Look

Nothing is more downtown style than a graphic t-shirt under a button down shirt. Finishing touch? A surfer styled beanie. Get the look here: Grey Button Down Shirt $34 / White Graphic T-Shirt 5 Euros / Indigo Skinny Jeans $49 / Grey Brimmed Beanie $11

Hipster Nerd Beanie Look

Hipster Nerd Beanie Look

Thanks to the Tech Wave nerds are pulling tons of ladies too these days.  Nerdy with a beanie, that’s geek swagger right there! Get the look here: Black cardigan $30 / Yellow graphic t-shirt $24 / Black Beanie $19.99

Sophisticated Beanie Look

Sophisticated Beanie Look

Beanies aren’t strictly for the artsy type, rock it with a full suit and be amazed how well it pairs.  Get the look here: Charcoal coat $94 / Black vest $60 / White Fitted Dress Shirt $39 / Black Pinstripe Pants $79

Lenny Kravitz Smooth Black on Black Beanie Look

Lenny Kravitz Smooth Beanie Look

Lenny Kravitz style is so bad ass and smooth, this beanie lover is typically a no fail type of dude. Goes to show you that wearing all black never fails. Get the look here: Black Blazer $52 / Black Tank $3 / Black Beanie $39

All American Boy Beanie Look

All American Boy Beanie Look

Throw a denim jacket on over a casual look, bam! You got an all American look.  Get the look here: Denim Jacket $105 / Skinny Jeans $50 / White V-Neck Tee $3 / Grey Beanie $13

Bad Ass Next Door Beanie Look

Bad Ass Next Door Beanie Look

Take the trailer-trash-chic white tank look and add some “I’m just from Brooklyn” style to it with this simple grey beanie. Laid back, calm dude next door look. Get the look here: White Tank $3 / Grey Beanie $8

Indie Hipster Beanie Look

Indie Hipster Beanie Look

Converse and beanies go together like James Bond and sexy women, it’s a given combination.  Accompany them with a comfy and basic jean and t-shirt look.  Get the look here: Grey Converse High Tops $50 / Jeans $49 / Grey T-Shirt $3 / Khaki Beanie $19

Beanie Friendly Outfits

Nature Hipster Beanie Look

Nature Hipster Beanie Look

Plaid Shirt $201 / Vest $175 / Brimmed Beanie $7 / Jeans $242 / Sperry Boots $59 / Belt Sold Out – Similar Belt $22

Hipster Quarterback Beanie Look

Quarterback  Hipster Beanie Look

Fleece Shirt $12 / Varsity Jacket $185 / Jeans $218 / Vans Sneakers $50 / Beanie $15 / Prada Sunglasses $340 

Navy Moto Jacket Beanie Look

navy moto jacket beanie look

Ralph Lauren Navy Moto Jacket $2995 / Burton Flannel Shirt / Jeans $630 / Beanie  / Prada Sunglasses $340

Stripes and Neutrals Beanie Look

stripes and neutrals beanie look

Striped L/S Shirt $61 / Bomber Jacket $300 / Khaki Pants Sold Out / Sneakers $70 / Beanie $7

Brown Casuals Beanie Look

Casual In Brown Beanie Look

Tank Top $5 / Jeans $30 / D&G Belt $110 / Beanie $25 / Prada Sunglass $340

Chino Beanie Look

Chino Beanie Look

Black Chino Pants $43 / Denim Shirt $34 / Converse Chucks $68 / Beanie $16 / Salvatore Ferragamo Sunglasses $276

Sweater Prep Beanie Look

Sweater Prep Beanie Look

Sweater $15 / Checkered Shirt $51 / Jeans $198 / Shoes $160 / Beanie $9 

Prep Master Beanie Look

Prep Master beanie look

Dress Shirt $88 / Jacket $105 / Pants $49 / Shoes $261 / Beanie $21

Checkered Beanie Look

checkered beanie look

Checkered Shirt / Skinny Pants $20  / Shoes $119 / Beanie $28

Dressy Surfer Beanie Look

dressy surfer beanie look

Long Sleeve Shirt $11 / Jacket $245 / Jeans $198 / Shoes $50 / Beanie $24

Classic Colors Beanie Look


Dress shirt $57 / Jeans $180 / Jacket $295 / Beanie $7 / Shoes $78

Retro Beanie Look

Retro Beanie Look

Cardigan $610 / Pants $49 / Watch $254 / Dog Tag Necklace $145 / Ring $49

Dapper Beanie Look

Dapper Beanie Look

Tank $3 / Jacket $171 / Pants $190 / Shoes $54 / Watch $190

Preppy Rocker Beanie Look

preppy rocker beanie look

Checkered Shirt $28 / Sweater $105 / Shoes $54 / Jeans $30 / Beanie $36

Patriotic Beanie Look

patriotic beanie look

Cardigan $49 / Jeans $198 / Shoes $54 / Beanie $34 / Sunglasses $340 / Plaid Shirt

Fun Bad Boy Beanie Look

Fun Bad Boy Beanie Look

Jacket $259 / V-Neck T-shirt Sold Out / Beanie $34 / Bracelet $130 / Shoes $69

Preppy Grunge Beanie Look

Preppy Grunge Beanie Look

Jeans $225 / Shoes $75 / Bracelet $350 / Tailored Shirt $33 / Beanie $75

Slim and Sleek Beanie Look

slim and sleek beanie look

Cashmere Sweater $680 / Pants $350 / Shoes $119 / Sunglasses $340 / Beanie $9

Rocker Bunyan Beanie Look

Rocker Bunyan Beanie Look

Flannel Shirt $25 / Pants $154 / Shoes $49 / David Yurman Necklace $3000 / Beanie $7

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