Styling one’s self during the winter time can be viewed in a few different ways. You can either go the easy route and only dress for warmth, or you can go the stylish route and push yourself a bit to come up with some interesting combinations. I (probably quite obviously) chose the latter to discuss for today’s post with Tommy Bahama.

One of the easiest ways to improve your style is to push pieces out of their ordinary and make them work in an unusual way. When most people hear Tommy Bahama, their minds immediately go to beachy, relaxed vibes, right? Well mine do too, but I would also argue that there’s no reason you can’t bring those comfortable beach vibes into your everyday life as well…even during winter! So today I’ve styled three looks surrounding Tommy Bahama pieces that all work for winter and will have you standing out in all of the right ways.

Look 1

In the first look, I definitely wanted to push myself to style one of Tommy’s famous camp shirts. These short sleeve button ups have been a TB staple for years and they’re actually what drove me to fall in love with the brand to begin with. This bold green and blue shirt screams summer on it’s own, but when you add it in with all of these other darker colors, it creates a pop of color that still fits well within a winter-appropriate look.

The pants are trousers from a suit, and the coat is heavy enough to keep me warm in cooler temperatures. It’s a great way to stand out without being too obnoxious. I’d recommend a look like this for a night out where you want to have a great time and be expressive but don’t want to blend in with everyone else.

Try it out for yourself by getting a bold colored shirt and styling it with dark colors. It will make the shirt pop and you’ll create a perfect blend of summer and winter fashion.

You can absolutely still wear your heaviest boots and get away with it. Just because you’re wearing something from Tommy Bahama doesn’t mean that you need to be wearing boat shoes. Think outside of the box and you’ll start to create looks that express your individuality.

Look 2

You’ll start to notice that a theme today is boldness. When I’m styling a brand that has excellent bolder pieces, I’m always going to take advantage. This fleece pullover is no exception. Most of us probably already own or have owned a fleece pullover sweatshirt. It’s nothing too new and different, but when you find one that’s unique like this you have to seriously consider pulling the trigger on a purchase. The reason I love it so much is that from a distance you’re not going to notice that it’s bold but then as you get closer and closer it reveals itself to be a statement piece.

The black sweater was great for winter, but I wanted to be sure I added some color into it so I threw on these green chino pants and added in the green bandana around the neck. If these moves are too bold for you, then you’d be totally fine to let the sweater do the talking and style it with some denim and a white tee. The fact that you’re wearing a sweater like this is enough to relay the message that you’re interested in having fun with your style.

Be open to boldness in the wintertime, guys. It’s boring to always be wearing plain blacks, grays, and navy. When you find something that fits in with the season but also makes a statement, it’s a go.

Look 3

Something that I’ve been focusing on lately is trying to be more aware of creating outfits that are a bit more masculine than what I might naturally put together. This blue striped overshirt was an easy piece for me to style in a more outdoorsy way. A great overshirt is something I’d recommend most guys have in their closet. It’s a perfect piece for layering over a henley like in today’s outfit for when the weather is chilly but not freezing. They also work really great buttoned up under a coat to keep you extra warm when it’s really cold out.

It’s frustrating to me when guys think that having good style diminishes their masculinity. That simply isn’t true. By being aware of what you like, what makes you feel your best, and how it should fit, you’re only going to look better. It doesn’t mean you have to start wearing the most fashion forward stuff, you just have to understand what makes you look your best.

Finishing the look with some slim fit denim, the blue beanie and these maroon boots was a fine way to tie everything together. When you’re creating your outfits – similarly to Look 1 today – when your look comes together with only one or two colors, add in a third for a nice break. This outfit is pretty much all blue and white, so the maroon boots add a nice contrast that compliments the rest of the outfit without distracting too much attention from everything.

That’s it! Three winter looks styled with amazing pieces from Tommy Bahama. Don’t sleep on them, guys. They have awesome stuff that’s really well made. It’s a perfect brand for your beach vacation but I would argue that I almost enjoy wearing it even more when I’m away from the beach because of how much it can boost my style.

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