How to Get Out of a Style Rut (Without Buying a Whole New Wardrobe)

We’ve all been there—you open your closet, see plenty of clothes, and still think, “I have nothing to wear.”

You’re not alone. One of our readers recently sent a message saying he felt stuck in a rut. He’s got plenty of great pieces, but it all feels…repetitive. Same old polo, same old pants, same old sneakers.

So today we’re tackling a simple question: What do you do when you feel like you’re stuck in a style rut?

I tackled this question in a video for Instagram, but let's unpack it here, too.

Start With What You Already Have

For this little exercise, I started with a very typical dad business casual outfit:

• Performance polo (micro-dot pattern)

• Five-pocket pants

• Woven belt

• Sneakers

• Watch

That’s our base. Totally fine. Totally wearable. Totally safe.

But if you want to add some dimension and confidence to your look—without replacing your entire closet—the easiest place to start is layering.

1. Add a Vest (a.k.a. the Dad Confidence Booster)

If there’s one thing I know about dads, it’s that we love a vest. I think a lot of dads view vests the way our wives view Spanx—something about them just makes us feel better.

A lightweight performance vest or quilted nylon layer instantly adds polish. It sharpens your silhouette, breaks up the monotony, and makes your outfit look intentional.

Just like that, you’ve leveled up. No extra effort required.

2. Layer With a Merino Crewneck

Next step: the merino wool sweater. Think of it as your secret weapon.

Pull one on over your polo, and suddenly you’re giving “I planned this” energy without actually planning anything. Go for contrast—a navy sweater over a light-blue polo, or a camel over white.

Still very much in dad territory, but with a bit of refinement.

3. Try a Chambray Shirt as a Layer

Here’s where it starts getting fun. Take that chambray shirt you already own—the one that usually gets worn solo—and layer it over your polo.

You’ll still feel completely comfortable, but now you’ve got texture and color contrast. Bonus: no one else in your office is dressing like this, and that’s a good thing.

4. Graduate to a Chore Coat or Workshirt

When you’re ready to push things a little further, grab a chore coat or workshirt.

It’s the same principle as the chambray—just a bit heavier, more rugged, and more interesting visually.

The green one I tried on in the video was from Target. The indigo blue version? That’s from Alex Mill, made in a heavier denim. Both look great. One’s budget-friendly, one’s premium. Either way, they do the job.

5. Swap the Belt and Shoes

You’d be amazed what happens when you change just two accessories: your belt and shoes.

Trade the woven belt for a classic leather belt, and switch from sneakers to loafers or chukkas. Suddenly, you’re giving off “sophisticated weekend guy” energy instead of “casual carpool dad.”

You’ll feel just as comfortable—but look a whole lot sharper.

6. Combine Layers for a Complete Look

Here’s where it all comes together:

• Polo

• Sweater

• Vest

• Loafers

Boom. You’re layered, polished, and still perfectly comfortable. Every piece you added already existed in your wardrobe—you just had to see it differently.

Get Out of That Rut

You don’t have to overhaul your closet to level up your look. You just need to re-mix what you already own.

Start with layering. Play with texture. Upgrade one accessory.

You’ll feel different immediately—and your coworkers, your spouse, and your kids will notice too.

Final Thought

Style ruts happen to everyone. But you don’t have to stay in one. A little experimentation can make your everyday outfits feel new again.

If you’ve got questions, ideas, or want help finding the right layering pieces, send me a DM or comment on Instagram. I love hearing from you.

Oh, and here's all of these links in one place.

See you next time,
— Leighton