I would think that by the sheer nature of me asking this question you’d already know my answer…but in short…yes! I’ve recently teamed up with my friends from Sharply, an awesome brand that does a wonderful job of creating really great basic, essential wardrobe pieces. The quality is much better than what you’re going to find at most big box stores. If you’re the type of guy who likes solid colors or if you’re shopping for someone in your life who needs quality, timeless clothing that fits great and will always look good – be sure to check out Sharply.

The reason I posed this question, can a gray hoodie be stylish?, is because from time to time I love to challenge myself to make something happen stylistically. Even someone like myself, who’s constantly involved in fashion related discussions, thoughts, and practices can have difficulties deciding what to wear or figuring out how to make a certain something work. Therefore, I thought that it would be fun to try and figure out how to make an everyday piece like this gray zip-up hoodie look like something that’s more than just a basic piece.

The reason behind all of this is simple. I’m sure you’ve all been in this position. You want to look nice but you also just can’t wrap your head around the idea of getting dressed up. It’s a day where you’re much more interested in comfort, but you also have to be aware of your appearance. This was the case for me, anyways, so I started with the hoodie and worked my way around the outfit from there.

I was going to wear a button up shirt under the hoodie but I remembered that sometimes it’s a bit uncomfortable for me, so I went with the next most comfortable piece that’s still stylish in it’s own right, the buttoned henley shirt. This is a piece I’ve been wearing like crazy lately and for good reason. It’s cozy but it also exudes a hint of stylishness.

I kept going back to the button up in my mind, so I decided that it could be cool to tie one around my waist as a shirt belt. That way I’d have it if I wanted it as a layering piece, but otherwise it could act on it’s own to add another level of style to my look. This is a super 90’s move, but it’s been coming back into style a lot lately.

By this point I was feeling pretty good about my top half, so I needed to start focusing on the rest of my outfit. I knew that I could always fall back on some dark denim, but I’ve been pushing myself to step away from jeans as often as possible lately. It’s a great way to push yourself into new areas and discover what other types of pants can bring to a look.

These houndstooth trousers were a great fit because their black and white pattern create a visually gray aesthetic when you look at them from a distance. Also, because a trouser is a much dressier pant than denim, they automatically take on a higher level of stylishness.

Another thing that I knew I wanted to avoid in this look was sneakers. That’s why I chose these high black boots. Sneakers are obviously one of my favorite things in the world, but when you’re trying to look nice with casual pieces, adding in a boot or a dress shoe is a smart move to dress things up. It’s the same concept as subbing in trousers for the jeans. It just looks nicer.

Last but not least to make this extremely comfortable hoodie as stylish as I could, I knew I wanted to add in some fun accessories. A clean watch, a subtle beaded bracelet, and a bolder ring were plenty to take things from casual to fashion forward. Never forget about the option to accessorize when transforming a look from casual to classy and stylish.

In the end, I’m very happy with how the outfit turned out. Challenging myself in these ways is a lot of fun. It’s something I would recommend to anyone who’s trying to hone their style skills.

Again, if you’re in the market for killer essentials or you still need a great gift idea for the guy in your life, be sure to check out Sharply! I’ve been wearing this hoodie as a layering piece a lot lately too. It works really well under a denim or leather jacket when the weather is really cold.

Questions? Comments? Find me on social media @parkeryorksmith or email me at parker@thelooksmith.com!

Don’t forget! Do it for you, not them!

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 parker@thelooksmith.com.

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