Upgrading my dad style wasn't something I planned—it kind of just happened. Like many guys, I settled into a routine of wearing whatever was comfortable and easy to throw on. Hoodies, sweatpants, old graphic tees—you name it, I wore it. It wasn’t until I caught my reflection in a store window, wearing a hoodie that had seen better days and sneakers that should’ve been retired years ago, that I realized it was time for a change. I wasn’t trying to land on the cover of GQ, but I wanted to feel more put-together. I wanted to dress in a way that made me feel confident, while still being true to myself.
This is the story of how I upgraded my dad style without losing the comfort and practicality that we dads value so much.
The Wake-Up Call
Let’s rewind to that moment in the store window. I was out with my kids, running errands on a Saturday morning. I looked like I had just rolled out of bed—which I probably had. My faded hoodie had a stain from breakfast, and my sneakers had holes I’d ignored for months. I didn’t feel good about myself, and I certainly didn’t look like I had it all together. It hit me that I’d been putting zero effort into my wardrobe. It wasn’t intentional; life just gets busy when you’rea dad. But I wanted to change that.
I went home, stood in front of my closet, and tried to figure out where to start. My wardrobe was a sea of hoodies, oversized t-shirts, and jeans that didn’t fit quite right. I knew I didn’t have to overhaul everything, but I needed a strategy.
Step 1: Start with the Basics
The first thing I did was identify what I liked about my current style and what I wanted to improve. Hoodies? Love them. They're comfortable, easy to wear, and practical for chasing kids around. But I realized that not all hoodies are created equal. Some looked sloppy, while others had a more polished vibe. I decided to invest in a few high-quality hoodies that fit well and looked sharp.
Instead of grabbing whatever cheap hoodie was on sale, I opted for neutral colors like black, gray, and navy. These were easy to pair with other items in my wardrobe and had a more elevated look. I also paid attention to fit—no more oversized hoodies that made me look like I was swimming in fabric.
Step 2: Discovering the Power of Henleys
Next up, I introduced Henleys into the rotation. If you’re unfamiliar, Henleys are those long-sleeve shirts with a few buttons at the top. They’re like the perfect middle ground between a plain t-shirt and a button-down shirt. What I love about Henleys is that they’re just as comfortable as a hoodie, but they instantly make you look more put-together.
I picked up a few in colors like olive green, charcoal gray, and white—versatile options that worked with almost anything. I’d pair them with jeans or chinos and feel like I actually tried, even if I only spent a few seconds getting dressed. Bonus: my partner noticed. “You look nice today,” she said one morning. That’s when I knew I was onto something.
Step 3: Swapping Out Old Jeans
Speaking of jeans, I realized my denim game needed serious work. Most of my jeans were either too baggy or looked like they belonged in a high school yearbook photo. I decided to invest in a few pairs of slim-fit jeans. Now, let me clarify: slim-fit doesn’t mean skinny jeans. It just means jeans that are slightly tapered and don’t drown you in fabric.
I went for dark washes because they looked cleaner and more versatile. I could wear them with a hoodie for a casual day or dress them up with a Henley and boots when I wanted to step it up.
Step 4: Shoes Matter More Than I Thought
I had always been the guy who wore sneakers everywhere. Don’t get me wrong, sneakers are great, but my old ones were beat-up and far from stylish. I realized that upgrading my shoes could make a huge difference in my overall look.
So, I invested in a pair of casual leather sneakers in white, which instantly made even my most basic outfits look so much better. I also added a pair of desert boots for those days when I wanted to dress up a bit more. Both options were still comfortable and practical but had a more grown-up vibe.
Step 5: Layering Like a Pro
Layering was something I’d never really done before, but it turned out to be a game-changer. I started experimenting with lightweight jackets, flannel shirts, and even denim jackets. Throwing a flannel over a Henley or adding a simple jacket to an outfit made me feel more stylish without trying too hard. Plus, layering is functional—great for unpredictable weather, which is perfect for a dad who’s always on the go.
Step 6: Accessories—The Finishing Touch
I used to think accessories were unnecessary, but I changed my mind after trying a few simple additions. A good leather belt, a casual watch, and even a beanie in the colder months added a little extra something to my outfits. These small details made me feel more polished and intentional about my style.
What I’ve Learned Along the Way
Upgrading my dad style wasn’t just about looking better—it was about feeling better. When I started dressing with a bit more care, I noticed a shift in my mindset. I felt more confident, more prepared, and, honestly, more like myself.
Here are a few key takeaways from this journey:
- Comfort is non-negotiable: If it’s not comfortable, I’m not wearing it. Period. The trick is finding pieces that are both comfortable and stylish.
- Fit matters: Even the nicest clothes won’t look good if they don’t fit well. I started paying attention to how things fit and even got a few pieces tailored.
- Quality over quantity: Instead of buying cheap clothes that wear out quickly, I invested in fewer, higher-quality items that last longer and look better.
- Versatility is key: I focused on building a wardrobe where most pieces could mix and match easily. This made getting dressed so much simpler.
Upgrading my dad style didn’t mean abandoning hoodies or comfort—it just meant being a little more intentional about what I wear. By swapping my old, worn-out clothes for better-fitting, higher-quality pieces like Henleys, slim-fit jeans, and clean sneakers, I feel more confident and put together. And the best part? I did it without sacrificing practicality or comfort.
So, to all the dads out there who think style has to take a backseat to everything else in life, I’m here to tell you it doesn’t. You can be a great dad and still look good doing it.
