How to Make Your Outfit Truly Yours

Clothes say things before you even open your mouth. They tell people if you’re confident, relaxed, bold, or trying too hard. They show whether you care about details or throw on whatever’s clean. And whether you like it or not, people notice.

But here’s what matters: your outfit should feel like you—not like some mannequin copy of a fashion ad. Not like a guy who just grabbed the latest trends because they’re trending. And definitely not like someone who’s trying to impress everyone but himself.

Understanding Your Personal Style

Finding Your Style Identity

Most men dress the way they were taught. Maybe your dad stuck to classic button-downs, so you do too. Or your friends live in hoodies and sneakers, so that’s what fills your closet.

But what if that’s not you?

Your style should match your personality, not someone else’s habits. If you like things clean and simple, a minimalist look—think neutral colors, sharp fits, and no unnecessary details—might be right. If you prefer rugged, go for heavyweight fabrics, earth tones, and pieces like the Boulder Haven Overshirt that add texture and durability.

Classic style? Stick with timeless cuts, button-downs, and structured layers. More modern? Go for slimmer fits, monochrome outfits, and sleek outerwear.

Inspiration vs. Authenticity

Looking at stylish men for ideas isn’t wrong. Copying them without understanding why something works is.

David Beckham pulls off tailored coats because they fit his structured, athletic build. Kanye makes oversized streetwear work because it matches his bold, unpredictable persona. You need to find what makes sense for you.

Instead of blindly following trends, start with what you naturally gravitate toward. Check your favorite outfits—what colors, cuts, and fabrics do you wear most? Which pieces make you feel your best?

Experiment, but don’t force what doesn’t feel right. If bold prints aren’t your thing, don’t wear them just because GQ says florals are “in.” Instead, go for a patterned option that still feels like you, such as the Sierra Heights Print Button-Down Shirt—subtle but not boring.

Being inspired is good. Forgetting yourself in the process is not.

Choosing the Right Clothes

Fit Is Everything

Nothing ruins a good outfit faster than bad fit. You could be wearing the finest fabric, the most expensive brand, or a perfectly coordinated look, but if it fits like a tent—or worse, a sausage casing—you’ll still look off.

Fit is the difference between effortless and awkward. It’s what makes a simple Birchwood Plaid Button-Down Shirt look sharp instead of sloppy. It’s why a $50 well-tailored blazer looks better than a $500 one that’s too big.

Here’s what matters:

• Shoulders: The seam should hit right at the edge of yours. Too wide? You’ll look like a kid in his dad’s clothes. Too tight? You won’t be able to move.

• Sleeves: They should end at your wrist bone, not halfway up your hand.

• Shirts: Fitted but not tight. If buttons pull or fabric bunches, size up.

• Pants: No excess fabric pooling at your shoes. A slight break at most.

Most men say finding the right fit is their biggest struggle when shopping for clothes. That’s because brands size things differently, and not all body types fit standard sizing. 

When in doubt, size slightly bigger. A tailor can take things in, but they can’t create fabric where there isn’t any.

Fabrics and Textures That Reflect You

Cheap fabric looks cheap. No way around it.

You don’t have to buy luxury brands, but you do need quality materials. They last longer, feel better, and make a huge difference in how an outfit looks on you.

Organic cotton, wool, and linen are solid choices. They breathe well, hold their shape, and age gracefully. If you hate stiff fabrics, something like the Everglade Quilted Overshirt is a perfect blend of comfort and style—warm, soft, and easy to layer.

Be careful with synthetic fabrics. Some, like polyester, trap heat and feel plasticky. Others, like elastane blends, add stretch and comfort. The key is balance—too much synthetic, and your outfit loses that natural, effortless look.

Texture matters, too. A crisp oxford shirt feels different from a soft flannel. A structured wool blazer adds presence, while a relaxed knit keeps things laid-back.

Comfort is a top priority when buying clothes, but comfort doesn’t mean sloppy. It means choosing fabrics that feel good and look even better.