How to Pull off Flannel on Flannel

At the Cape Neddick Lighthouse in Maine, which you can read more about here, it was extremely windy by the water. As I was getting blown away, Dan was actually loving the cool weather and what he considered a “slight breeze.” Since he managed to keep his composure by the ocean, I thought we would share Dan’s obsession with flannel shirts and how he likes to wear them.

When I first met Dan in high school, his closet was FULL of flannel shirts. And ONLY flannel shirts. With this being Dan’s signature style, it was no surprise seeing him wear flannel on flannel out in public. If you want my opinion on this, as long as he doesn’t pop both his collars at once, I don’t see any problem with doubling up.

How to Wear Men's Flannel Shirt / New England Style Blogger / Simply Lovebirds

Over the past few years, I have actually fueled his obsession with flannel by buying him EVEN MORE of these fuzzy plaid long-sleeves. During Christmas time, he’s always overjoyed to unwrap a new flannel button-down to add to his collection. Currently eyeing this shirt for him from L.L.Bean.

How to Wear Men's Flannel Shirt / New England Style Blogger / Simply Lovebirds

Not to mention, his mom likes when I buy him flannel too. Guess how he had all those flannel shirts to begin with? (Hint hint: mom).

How to Wear Men's Flannel Shirt / New England Style Blogger / Simply Lovebirds How to Wear Men's Flannel Shirt / New England Style Blogger / Simply LovebirdsHow to Wear Men's Flannel Shirt / New England Style Blogger / Simply Lovebirds

Let’s take a look at Dan’s backpack. It may look like an ordinary backpack to you, but I’ll let you in on a little secret. This bag discreetly holds all of our camera gear! There are so many details that I can share about this backpack. If you guys are interested, I might review this camera bag sometime in the future.

How to Wear Men's Flannel Shirt / New England Style Blogger / Simply Lovebirds

Click for more details on Dan’s dock shorts. So comfy!

New England Style Blogger / Simply Lovebirds

You’ll be surprised to hear that none of these photos are posed! Yep, Dan just walks around in a heroic stance all day. He blames it on his broad shoulders and the fact that his body is shaped like an “upside-down triangle.” I wouldn’t be able to get a posed shot of Dan if I begged for it, as he refuses to tolerate such awkwardness.

New England Style Bloggers / Sperry Boat Shoes / Simply LovebirdsHis and Hers Matching Sperry Boat Shoes / Simply Lovebirds

Now for an unsponsored message—not that any of this was sponsored. This past summer, Sperry boat shoes have been our go-to shoes. They’re so easy to slip on and off. We love the nautical look which just screams New England. While we would never recommend hiking in these, boat shoes work really well in wet areas! Even more so, we love that Sperry’s sells similar styled shoes for both men and women. It makes it that easier for us to match!

We hope you enjoyed that glimpse of Dan’s New England style!

How do you feel about wearing flannel?

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How to wear a flannel shirt like a New Englander / Style Blogger / Simply Lovebirds How to wear a flannel shirt like a New Englander / Style Blogger / Simply Lovebirds


  1. October 16, 2017 / 11:46 am

    Ahahaha this felt like reading a post about Chris! He hates having to pose for photos too because that’s when he gets super awkward.

    Love that you keep adding to Dan’s fueling obsession for flannel – that’s too cute!

    cabin twenty-four

    • October 17, 2017 / 10:18 pm

      Ahaha I feel like guys are all that way! Thanks Eena!

  2. October 16, 2017 / 11:54 am

    What a great idea to wear shirt over shirt, very stylish and unique indeed! Perfect transition look on cooler days, I love it. Have a great day.

    xx Simone
    Little Glittery Box

    • October 17, 2017 / 10:16 pm

      Thanks! His layering was really out of necessity because it was so windy, but I thought it looked alright!

    • October 17, 2017 / 10:16 pm

      Thanks, Violette! Maine is gorgeous and I hope you visit someday! We wrote about the Cape Neddick Lighthouse on the blog earlier, which you should check out.

    • November 2, 2017 / 10:03 am

      Thank you!

  3. Keri Elaine
    October 16, 2017 / 2:35 pm

    He’s too cool to pose and it worked out fabulously! Must have something to do with the photographer 🙂
    Keri Elaine

    • October 17, 2017 / 10:15 pm

      Omg you are too kind! Finally someone notices the photographer HAHAH 😉 But no, Dan is pretty natural compared to my awkwardness in front of the camera.

  4. October 16, 2017 / 3:30 pm

    I do like a flannel shirt on a guy! My boyf only has one, should really fuel this obsession! x

    • October 17, 2017 / 10:14 pm

      Oh definitely! The holidays will come up before you know it!

  5. October 16, 2017 / 3:34 pm

    I love flannel and own far too many. I just gravitate to them in the store haha.

    Nat ◇ dignifiable

    • October 17, 2017 / 10:14 pm

      Nah girl, you can never own too much flannel!

    • October 17, 2017 / 10:13 pm

      Thanks Jennifer!!

    • October 17, 2017 / 10:13 pm

      Yeaahhh… he’s pretty low maintenance that way!

    • October 17, 2017 / 10:13 pm

      Right? Such a guy thing to own!

  6. October 16, 2017 / 7:44 pm

    It’s funny how guys get their one thing and then they stick to it forever! My dad started wearing Sperry’s in the early 80’s and we’ve had to buy him a new pair in brown every Christmas since.


    • October 17, 2017 / 10:12 pm

      Aw I love that he asks for them every Christmas. What a cute story! You really spoil him! My mom is the same way with fuzzy slippers.

    • October 17, 2017 / 10:12 pm

      They’re definitely classics! Thanks for the comment, love!

    • October 17, 2017 / 10:11 pm

      Thank you, Doreen! This backpack is so functional and pretty ordinary looking, so it doesn’t attract too much attention from thieves! I would love to write up a review sometime for you!

  7. Gabrielle
    October 17, 2017 / 7:43 am

    ”Just walks around in a heroic stance” – haha, not a bad attribute to have! I love how you’re both wearing matching deck shoes, so cute! I feel as though I need to spend more time beside the sea, because it can be so calming and comforting.

    • October 17, 2017 / 10:10 pm

      Aha I wasn’t sure how else to describe it! 😉 It’s definitely noticeable if you met him in person, at least back in our high school days! I bet you would really enjoy some time by the water! Treat yourself, girl! And thank you so much for taking the time to comment, Gabrielle!

  8. October 17, 2017 / 9:22 am

    I love those shoes! They look super comfy and I’m allllll about comfort 🙂

    • October 17, 2017 / 10:05 pm

      Yesss! My Sperry shoes have memory foam on the bottom which is beyond comfortable! Now I have to make an effort NOT to wear these shoes everyday.

  9. October 17, 2017 / 12:56 pm

    I always snag my boyfriend’s flannel- great for layering!

    Le Stylo Rouge

    • October 17, 2017 / 10:06 pm

      No wonder we have the “boyfriend fit” in all types of women’s clothes haha. So comfy!

    • October 17, 2017 / 10:06 pm

      Thanks Brooke! 🙂

    • November 2, 2017 / 10:04 am

      Hahah yeah Dan has silly style. I don’t think I would be brave enough to wear this either hah!

    • November 2, 2017 / 10:26 am

      Thanks Amy Ann! It was so windy, he had to layer!

    • November 2, 2017 / 10:26 am

      They’re comfy, aren’t they?!

  10. October 18, 2017 / 8:06 pm

    I’m loving these photos, and that camera bag is very cool! I would definitely love to hear a review about it!

    • November 2, 2017 / 10:26 am

      Thanks! I will have to get started on my review then!

  11. October 18, 2017 / 8:24 pm

    Ooh, the shirt you’re eyeing from L.L. Bean looks SO comfy!!! I can’t believe all the photos are un-posed LOL. Oh and my mom is in love with those Sperry boat shoes, too!!

    • November 2, 2017 / 10:27 am

      Hehe I know, I should probably buy it now before it sells out! Thanks for your comment!

  12. October 19, 2017 / 10:33 am

    I love a good flannel shirt! There are so many ways you can incorporate them into an outfit (for girls at least) and one of my favorites is the waist wrap around!

    • November 2, 2017 / 10:28 am

      I love that too! Will have to wrap flannels around my waist more often!

  13. October 19, 2017 / 2:38 pm

    Flannel is one my favorite parts of fall!! And these pictures are gorgeous.. I’ve always wanted to visit Maine. You two are just the cutest <3

    xo, Allie

    • November 2, 2017 / 10:29 am

      Aw thanks Allie! Hope you get a chance to visit Maine someday!

    • November 2, 2017 / 10:30 am

      Thanks Katherine! Dan’s layering probably looks good because the bottom flannel is such a light color. Perhaps you can try layering your subtle flannels!

  14. October 20, 2017 / 7:23 am

    I can imagine Dan’s room filled with flannel shirts. First, it looks classy, second, its wearable to almost any season. I love your boat shoes- the two of you.

    StyleSprinter Blog by Katya Bychkova

    • November 2, 2017 / 10:30 am

      Thanks so much Katya! He’s got way too much haha but you’re right, it’s a classic!

  15. October 20, 2017 / 12:57 pm

    I love this Kim! I absolutely love flannels, I think they’re so cool and comfy – and I love Dan’s style, too! Also, lovely photos! I wish Scott and I posed so naturally, haha!!

    I hope you’ve had a great Friday,

    • November 2, 2017 / 10:31 am

      Oh what do you mean? You and Scott pose so naturally too! And I’ll be sure to let Dan know that you like his style. Thanks so much for the lovely comment!

    • November 2, 2017 / 10:31 am

      Thanks so much!

    • November 2, 2017 / 10:31 am


  16. October 21, 2017 / 6:37 pm

    I would never think to do flannel on flannel. Gotta show my hubby the post! Beautiful photos btw!

    Rina Samantha

    • November 2, 2017 / 10:32 am

      Hope he gets inspired! Thanks so much!

  17. October 21, 2017 / 8:01 pm

    This is so cute! The best thing about his flannel obsession is that you get to steal all of his cozy cute shirts! And I’m loving the Sperry shoes. I think that might be one of Ben’s Christmas presents (shhhh…). He loves boat shoes!

    Susie |

    • November 2, 2017 / 10:32 am

      So true! I lived in his flannel shirts when we first started dating! I bet Ben will love the boat shoes for Christmas! I won’t tell him 😉

  18. October 21, 2017 / 9:23 pm

    Dan looks great in that flannel. 🙂

    • November 2, 2017 / 10:33 am

      Thanks Britney! I’ll let him know you said that.

  19. October 22, 2017 / 3:03 pm

    I didn’t even realize Dan was wearing another flannel under his flannel until you mentioned it XD. Dan pulled the flannel on flannel look flawlessly! If SoCal gets really cold, I need to recommend this to my boyfriend XD. Haha, his mom did right by hinting at the flannel gifts XD. YASSS Sperry shoes are so comfy and look so hip! I haven’t worn a flannel in years but they’re so comfy!

    • November 2, 2017 / 10:35 am

      This one is a pretty subtle look! We did it mainly because it was so windy and he didn’t bring a jacket with him. So glad you thought he pulled it off though! And I’m lucky that his mom stocked his wardrobe with flannel shirts because it’s such a classic! Hope you get great weather in SoCal this fall/winter!

  20. October 23, 2017 / 5:50 am

    I adore flannel on men and on women! It feels so cozy this time of year. LL Bean makes so many great flannel shirts. Maybe Dan would like to model a bow tie from The Maine Square in the future???

    • November 2, 2017 / 10:39 am

      We basically live in flannel during the fall and winter time! And we love the idea of modeling for The Maine Square! Just shot you a quick email!

  21. October 23, 2017 / 8:47 am

    I like flannel on boy and also on girls sometimes. You did very nice pics of your man.
    Your shoes pic is so cute <3

    • November 2, 2017 / 10:39 am

      Thanks Carolina!

  22. October 23, 2017 / 7:54 pm

    This is the perfect New England preppy look, love it and the gorgeous scenery!
    xo Annie
    New England Romance

    • November 2, 2017 / 10:41 am

      Thanks Annie! You can’t beat a lighthouse view.

  23. Amy-Anne Williams
    October 24, 2017 / 7:48 am

    Oooh this is a LOOK, it’s super trendy. I love the location too, you could not have chosen a more beautiful place to shoot these photographs. Adore the outfit as I’m a massive fan of flannel as it is, and mixing things up like this is what I liveeee for!

    Little Moon Elephant

    • November 2, 2017 / 10:44 am

      Omg thanks so much Amy! You can’t beat a view of the ocean and an iconic lighthouse in Maine hehe.

    • November 2, 2017 / 10:46 am

      Not many people do! Wanted to throw a curve ball at you all hahah.

  24. October 25, 2017 / 9:09 am

    You two are adorable! My boyfriend loves his flannel shirts as well, haha. But they can definitely be styled well! Great shots!

    Looks by Lau

    • November 2, 2017 / 10:47 am

      Thanks Christina!

    • November 2, 2017 / 10:48 am

      Thanks Nina!

    • November 2, 2017 / 10:51 am

      Thanks Merel!

  25. October 28, 2017 / 4:37 am

    I love the layered look. Although I’m always unsure if I should get a larger size so the layers don’t fit too tightly.

    xx Yasmin

    • November 2, 2017 / 10:52 am

      True. With flannels sometimes you have to size up or get the boyfriend fit which is slightly larger!

  26. October 28, 2017 / 6:57 pm

    Maine looks beautiful. I am enjoying all of your photos there! The flannel shirt looks good on him. And the boat shoes are classic!

    Jessica |

    • November 2, 2017 / 10:52 am

      Thanks Jess! We love boat shoes!

  27. November 1, 2017 / 11:54 am

    Flannels are the best, and I love the flannel on flannel look! That’s such a clever idea that I’ve never seen before. And I haven’t owned a pair of boat shoes in forever, but they really are great. x

    x Kara |

    • November 2, 2017 / 10:53 am

      Thanks Kara! Definitely throwing a curveball here since no one ever wears flannel on flannel haha.

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