The Tailored Boyfriend Button-Up – A Classic

May 12, 2020

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My spring closet clean-out, organization and assessment of gaps revealed to me that I could use a couple of a classic that is actually a hybrid: the tailored boyfriend button-up shirt.

Whether you choose to tuck it entirely, French-tuck it, or leave it entirely un-tucked, the tailored boyfriend style offers movement with grace, classic structure with comfortable ease and versatility.

While I have worn the two I currently have from Shirtini to work and for errands, I also have worn them while gardening. Initially, this may sound excessive – why dress well for gardening? But, hear me out.

I had the good fortune of living across the street from the most well-coiffed garden for four years while living in my rental in Bend. The woman behind the garden was a 70-year-old master green-thumb who was regularly outside (morning, evening, but never the height of the heat early afternoon during the summer). What was she wearing? Collared button-up shirts, sleeves rolled, comfortably straight-leg denim and her garden hat. Sometimes a jacket was necessary, but her trusted go-to gardening uniform included the button-up. Often untucked as the top was tailored and still allowed movement, and always long enough to enable her to reach, bend-down, stretch, etc. comfortably.

I took note. Granted, when I know I am going to get dirty for the BIG projects, I wear grubby clothes, but I have started to wear my collared shirt over jeans (and am now searching for some cotton-khaki and navy pants as well), don my gardening hat, slip on my wellies and get to work.

In an effort to demonstrate the versatility and classic nature of the boyfriend button-up (some are more tailored than others), I have pulled some images for inspiration. I have also shopped a few items for you at the end of the post. (Click on any of the images to be redirected to the original source.)

~Shirtini Boyfriend Shirt, 40% off, all sizes~


19 thoughts on “The Tailored Boyfriend Button-Up – A Classic

      1. Or if you already have a few in your closet, do what I’m planning on doing: Pull them out and, using the photo’s as inspiration, try styling them in new ways. Voila, a fresh look for zero dollars 😉

    1. It never hurts to be on the lookout for good deals. I was thinking today how much I’d appreciate a quality button down shirt. Thank you for sharing Shannon!

  1. Shannon, I have a gardening apron , which is made of canvas , with bound seams and two double pockets on each side , two deep ones and two ordinary depth ones.

    It’s great for protecting whatever I have on underneath , and no matter how grubby it gets when I’m gardening , once popped into the washing machine , comes up like new.

    I must have had it for at least ten years , and use it constantly.
    I can’t remember where I got it from , and the label is unreadable now because of the years of use and laundering ? but I wouldn’t be without it.

    On the subject of shirts , I have used an oversized white voile shirt as a beach cover up for probably just as many years !

    Thank you for continuing to post , love reading and listening to you .
    Stay safe and well ,
    Best wishes from the UK

  2. Ah yes!!! A lesson we’ll learned from the elegant Kathryn Hepburn…whom, if I’m not mistaken, wore men’s shirts…

  3. Upon your recommendation, I ordered two shirts from Shirtini–I love them !! I wear them often and feel so chic!! Thank you!!

  4. Perfect classic shirts. I never know whether to tuck them, leave them out or half tuck. I wear shirts like these most of the time, but never sure what to do with the tail.

  5. One can never have too many button downs. I am eyeing a denim as mine is showing signs of wear and tear.. In France overalls (une combinaison) are worn by workers. They come in diffetent colours depending on what type of work you do. I wear one in grey and red for gardening a la Ripley(Alien)?. Keeps everything in place. I was amazed in the 70’s when I arrived in England and saw men cutting the grass in a tie and jacket and even smoking a pipe on occasion. They looked very smart

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