Here’s the thing. I always loved shopping for new clothes. Whether it was going to Kohl’s with my dad in 4th grade or shopping for my first job at Banana Republic after college, I was always excited to pick out something new.

But there was no rhyme or reason to what I bought. I chased sales. I picked random items that didn’t match anything else in my closet. I could never figure out what to wear and the anxiety would hit hardest before events. Date nights. Birthday dinners. I’d be stuck staring at my closet thinking, none of this goes together.

Around my 30th birthday, I finally had enough. I started asking my wife Gianna for help. I began investing in better quality pieces. Little by little, things started to click.

The biggest breakthrough came when I simplified my wardrobe. I got rid of anything I wasn’t wearing and started building a wardrobe off the basics. A solid white t-shirt. Dark jeans. Clean white and blue button-ups. Once I had fewer, better items, it was easier to match things without asking for help.

Then I discovered Gemini, a boutique clothing store in Wicker Park that completely shifted how I saw style. They introduced me to new materials, unique brands from other countries, and timeless pieces that felt elevated but still authentic to who I am.

Everything felt timeless, elevated, and still me.

But here’s what surprised me. Even after building a better wardrobe, I still found myself stuck. Just because you own good clothes doesn’t mean you instantly know how to style them. You need ideas. You need to see full outfits on real people.

I started searching online, but most of what I found was either super trendy, overly formal, or just plain off. There are only a handful of solid male style creators out there, and they get lost in the shuffle of bad search results and outdated advice.

That’s what led me to create SimpleMensStyle.

I wanted a space where men could find realistic outfit ideas that feel simple but elevated. Where it’s easy to see how to style the clothes you already have, or get inspired to try something new from a brand you’ve never heard of. No fluff. No crazy trends. Just good style made easier.

If you’ve ever felt stuck getting dressed or overwhelmed by too many options, this is for you.