How to Expand Your Style Comfort Zone | Part 1: Finding Inspiration5 min read

We all have our personal comfort zones when it comes to getting dressed.

Maybe you’re a jeans and t-shirt kind of guy. Or maybe you throw on a crisp, fitted polo or button up, a pair of khakis, casual sneakers, and call it a day.

Some days I don’t want to think about what to wear, so I default to what I feel most comfortable, yet stylish wearing—A pair of dark wash denim or straight-leg chinos paired with a clean, untucked button down shirt and a pair of suede derbies.

Sure, it’s a fine choice and absolutely acceptable, but it’s not allowing for me to explore and break free from my comfort zone.

Just a note–this is part one of a three part series. You can jump ahead to part two here or part three here.

cover photosIf you’re interested, I’ve compiled the entire 3-part series into a handy PDF that you can download for free, print and read at your leisure. Simply enter your name and email and I’ll send it right away.

How To Expand Your Style Comfort Zone: Finding Inspiration | Gentleman Within

Do you ever feel like you’re in a style rut, wearing the same things over and over again?

If so, here are some tips and insight on finding style inspiration and how to expand your style comfort zone.


Let’s get started.


Ryan Goseling Style Inspiration
“Hey girl, I heard you like my style.” —Ryan Goseling

Do you have a style icon? Is there someone (doesn’t have to be famous) whose style you’ve always admired? Do you know what you like about his style in particular?

If you can answer these questions, good. You’ll want to be able to pinpoint the exact items you like.

You may wonder where he got his jacket or slick watch. Maybe there’s something about the way he layers his clothes or harmoniously blends colors, and adds texture.

Or maybe he’s mastered the first rule of men’s style.

Whatever the case, you’ll want to take note of the details. Get specific on what you like. Don’t just observe, but observe and take mental notes.

There are a lot of men who won’t say that they’re impressed by another guy’s style, but it’s the confident ones who can openly admit it.


I Am Galla Pinterest Style Inspiration
I Am Galla on Pinterest has an amazing collection of sharp casual looks.

Are you on Pinterest or Instagram?

A simple search of “men’s style” or “men’s smart casual” on Pinterest will yield a collection of style inspiration to draw from and boards to follow.

Hashtags like #menstyleblogger, #styleformen#menswearblogger and #sartorial on Instagram are a good starting point.

As you browse, you’ll see a lot of trendy looks that seem beyond your comfort zone, but try to pick out one item in the outfit that you’re drawn to.

The Dressed Chest Instagram Style Inspiration
I recommend checking out The Dressed Chest for some great style and outfit coordination.

Maybe it’s a stylish pocket square or tie bar. Start to think about how you’d incorporate it into your outfits.

If you haven’t set up any boards on Pinterest yet, now’s a good time.

Create a ‘Style Inspiration’ or ‘Style Goals’ board and start pinning things that stand out to you. Over time you’ll have your very own curated collection of style inspiration. You can keep the board private if you like.


While the internet is great, it’s also a good idea to look for style inspiration out in the real world.

Start studying people. If you spend time at the coffee shop, give yourself a few minutes observing the people around you.

Take mental notes. Try to break down someone’s style and maybe think about why that person decided to wear what he did.

By becoming conscious of what people are wearing, over time you’ll begin to appreciate style and learn what you like and don’t like.


If you want to stay organized, an app like Evernote is great for collecting and organizing your newly found style inspiration. Of course you can use any other note-taking app you like.

I personally use Evernote to organize everything from my goal planning to my editorial calendar. It definitely tops my list of useful apps.

Once you’ve picked your app of choice, you’ll want to create a “Get List” of things you want to buy down the line. Continue adding to the list whenever there’s a new piece you want to try. Check off the ones you get.

This will keep you organized and remind yourself of key pieces on your list for the next time you hit up the mall or do your online shopping.

Pin it button example
Pro tip: download this extension for your browser of choice and you’ll be able to pin style inspiration with one click. Boom!

By organizing and curating style inspiration—in time—your mind will activate. Taking deliberate action makes you more likely to cement your goals. In this case, expanding your style comfort zone.


So now you have all this style inspiration and knowledge of what you like and don’t like.

What’s the next step?

  • Start imitating what you like
  • Experiment
  • Make mistakes
  • Rinse and repeat

You’re not a poser or a fake.

It’s how we learn.

We all start somewhere.

You might find yourself overwhelmed with style options, wanting to try everything all at once.

Go for it.

Do you like the way it looks?

Does it feel good?

That’s all that matters.

Get out there and try things on.

Incorporate the elements of style you like.

Eventually you’ll begin to uncover your own sense of style.

Learn to steal like an artist.

There’s a great quote from Austin Kleon’s book, Steal Like An Artist.

“Nothing is original. Steal from anywhere that resonates with inspiration or fuels your imagination. Devour old films, new films, music, books, paintings, photographs, poems, dreams, random conversations, architecture, bridges, street signs, trees, clouds, bodies of water, light and shadows. Select only things to steal from that speak directly to your soul. If you do this, your work (and theft) will be authentic. Authenticity is invaluable; originality is nonexistent.”
Jim Jarmusch

It’s worth repeating.

By stealing what you like, you’ll expand your comfort zone and ultimately begin to develop your personal style.


Fast fashion logos

There’s something to be said about quality of clothing. It’s always my recommendation to buy quality made goods over cheaply made clothing, at least whatever you can afford.

But I believe that when getting started, it’s okay to seek out fast fashion like H&M, Zara and Uniqlo. They typically offer trendier, form-fitting clothes for extremely affordable prices.

This is perfect for purposes of experimentation. Don’t be afraid to try on new things that you’ve always wanted to, but never did.

Get that scarf, suspenders, bowtie, and blazer.

Go f’n crazy.


You’re good at playing it safe. We all are. But this is the beginning of your conscious style journey.

And in order to expand your style beyond what you’re used to—you have to find inspiration and get out there.

Experiment and try new things.

You might crash and burn, but you’ll learn about what you like and don’t like in the process.

The key, as with anything in life, is to actively implement what you’ve gathered.

This is how you’ll begin to expand your style comfort zone.

In the next part of this mini-series, I’ll talk about ways to begin incorporating some of the pieces you’ve observed, liked and saved—into your style rotation.



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