One of my favorite summer trends over the last couple of years are bold button up shirts. There’s something wrong with that statement, though. Even I termed them as a “summer” trend, which is incorrect. I want to see bold button ups being styled all year.

I recently scored two sweet new shirts from my friends at Sharply, a brand that I loved for their basics and just recently entered the world of prints and button ups. The reason I say that I want them worn all year is because, in my experience, life is more fun in a bold button up shirt. You grab attention without being obnoxious, people see you and know you’re ready to have a good time, and when they fit right, you will exude a certain level of confidence that doesn’t always come from a basic shirt.

There are some slight adjustments you can make when wearing these shirts during the fall and winter, and I’m going to share those with you.

Dark Accents

First, if you’re wearing a bold button up during winter, let the shirt do the talking by surrounding it with dark pieces. I wore some dark black chinos and black boots because I didn’t want to be too bright. If it’s an occasion where bright works, then embrace it, but otherwise, I would recommend this move to allow the shirt to pop but while also avoiding looking like you’re dressed too much for summer.

I couldn’t resist enjoying an ice cream sandwich while rocking this shirt. It was too meta to pass up. The pop of color in the socks is another easy touch that can remain hidden unless you sit down or your pant legs rise up for some other unforeseen reason.

By treating your entire outfit like something you would normally wear during fall, and then substituting the bold shirt, you’ll look like you’re perfectly styled for this awkward time that’s part summer and part fall.

Embrace the Bold

If you’ve followed along for awhile, you’ve seen me wear this pink suit a few times. I omitted the jacket in these photos so I could fully show off the awesomeness of this flamingo button up, but don’t be afraid of saying f**k the calendar and dressing for the weather. It seems like it’s been staying hotter a bit longer this year, so don’t be afraid to go full on with the boldness.

Wearing nicely fitted trousers is a great move during fall. They’re a perfect alternative to denim or chinos if you want to dress up a bit. Especially in these in between months of September and early October, when the weather is still warm enough to not warrant a jacket, let your clothes make a statement.

If pink pants are too much for you, that’s totally fine, but don’t be afraid of wearing something outside of your comfort zone. The more you start to slowly push your own boundaries, the sooner you’ll be comfortable making bold moves and then something that seemed crazy six months ago has now become your norm. That’s how you develop style, by pushing yourself to new places and finding out what works best for you.

Regardless of how you like to style it, don’t stow those bold shirts for winter just yet. By inserting them into otherwise typical fall looks you can get away with boldness much later into the year. Also, depending on where you live, going bold all around is fun too. Don’t hide behind a heavy coat, layer yourself with interesting things so you can stand out and create some excitement around what you’re wearing.

Check out these shirts as well as other fun options from Sharply. The quality is excellent and the fit is comfortable and slim in all of the right places.

Questions? Comments? Find me on social media at @parkeryorksmith or email at!

About the author

I'm Parker York Smith, a curious dude still very much figuring everything out. I hail from the Midwest but have been dwelling in Los Angeles for the last few years being a pretty stereotypical west coast transplant. I'm a fashion geek, I love to walk (a LOT) and I do my best to find the bright side. I'm extremely excited about this blog and hope that (with some hard work and luck) it turns into what I believe it can. If you have any questions, comments or concerns, please get in touch with me via my social networks (which can be found in the sidebar) or email me at

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