Style and dressing well, at its core, is motivated by our desire to stand out. Primally, we want to set ourselves apart from the pack, to be noticed… in a positive way.

One of the ways to do this in our modern world is to make sure we dress sharp.

How we dress not only says how we feel about ourselves, but also how much we respect others around us, and where we belong in society, what tribe we’re a part of.

A quick thanks to our friends at Col. Littleton for sponsoring and being a part of this article. I thought I’d seen tough leather goods before, but what I’ve touched and owned previously is nothing compared to their stuff.

I’ll be sure to show you some of my picks in this article.

The colonel is giving a special gift with every purchase between now and 12/31 to all EG readers. Just enter “EffortlessGent” in the order notes at checkout.

1. Choose quality over cost

I’m all about investing in things you can keep for a long time.

Once you find something you like and fits well, buy the best you can afford. Look for timeless pieces—a great pair of jeans, a crisp white dress shirt, a nice pair of leather loafers—and invest in them. But don’t baby them!

Wear the shit out of them. Enjoy them. Get your money’s worth.

Plus, stuff looks better when it’s a bit worn in. Age and wear on a quality pair of jeans or a sturdy leather bag give it character.

The same advice goes for your accessories. When I work at coffee shops or head to meetings around NYC, I usually take a briefcase or bag with me so my stuff is protected.

colonel littleton saddlebag briefcase american buffalo

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Not only do I want the bag to be rugged and able to withstand all the abuse, I need it to match my style and personality. And frankly, I don’t want to carry around an ugly ass bag. So I need it to look good, too.

2. Have a signature piece

Whether that’s a great leather bag, a unique belt, a well-designed card holder, or something else, treat your signature piece like your calling card.

Think of Cary Grant and his suits, or Paul Newman and his Daytona.

If you’re anything like me, you enjoy catching people off guard. And you like a good story. That’s another reason I’m into Col. Littleton’s stuff.

Not only are they a great example of quality + personality, but at first glance, they’re not the type of products casual observers would expect me to wear and carry.

They’ve been around almost 30 years – since 1987 – and have been designing, cutting, sewing, and finishing their goods by hand in a tiny town south of Nashville, Tennessee (population: 327) ever since.

Even though Hollywood legends like Robert Duvall and Robert Redford are customers and fans -and they’re carried in many well-known stores from Orvis to Neiman Marcus – the brand has stayed true to their Americana roots this whole time.

What I like most of all is the character in each piece. I’ve now owned quite a few of their accessories, and I can attest to their rugged authenticity.

This isn’t your pretty, smooth, overly-treated leather. This is leather with character, leather that can take (and probably has taken) a beating. You may see branding marks (a special request), bug bites, and scars, but that’s what gives these goods character, and I love that.

My wife, Kate, had coffee with a friend in Central Park the other day, and I stopped by to say hi. I had my buffalo saddlebag slung over my shoulder.

When Kate met up with me later, she couldn’t wait to tell me what her friend said: “Sarah saw your bag and she loved it, she thought it was absolutely beautiful.”

colonel littleton saddlebag briefcase american buffalo

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I don’t usually look at my bags as beautiful, but, fellas, if a woman says that about your bag, you know you’re onto something.

Let your signature piece be something you’re proud of and happy to be seen wearing, even known for.

3. Be the trendsetter

Here’s the thing: A lot of us are afraid of standing out. We want to blend in, not cause a ruckus, not be noticed.

That’s fine. But sometimes, we take that too far.

We wear ill-fitting clothing because everyone else at work does (i.e. basically every politician in Washington, D.C.).

We tell ourselves we don’t care about how we dress because no one else in town seems to care either.

What if we approached it a different way? What if, instead of blending in, we made a point to stand out and look our best? What if, by doing this, we up everyone else’s game?

Here’s a great example of standing out and being noticed in a good way, from EG reader, Andrew H:

Today a male colleague literally stops me when I’m walking by and says “Seriously, where do you buy your clothes? You look fantastic!” That was one of FIVE compliments today and it’s just lunchtime…

Later, he emailed again and told me how the rest of his day went:

I finished the day with about 15 compliments. I went into one department today to meet someone for a meeting. The department is all women. When I get there she says ‘wow, you look fantastic!’…and drags me into a few offices to show her colleagues.

Then we are meeting and she says ‘can I give you a compliment?’ Of course I say yes. She says ‘you look good always but today you look so dapper…like out of a magazine’. I laughed…I’m getting better at showing genuine appreciation for compliments.

BOOM.

Dress a little better than everyone around you.

Raise the bar and inspire others to come up to your level.

Wear a tucked-in OCBD shirt to class when everyone else is wearing T-shirts and sweats. Wear a sport coat and tie to work even if no one else does it.

Don’t look at it as being the lone wolf. Look at it as being a trailblazer.

Maybe, in your own little way, you’ll inspire them to care a bit more about how they present themselves.

4. Pay extra attention to the smallest details

Shine your shoes. Iron your shirts. Maintain a sharp crease in your trousers. Brush your coats when you see lint (here’s the brush I use, by the way).

Shower regularly. Brush your teeth (and floss!) regularly. Take care of your body. The list goes on and on.

colonel littleton no.4 shoeshine kit

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Basically, “stay crispy”, as the kids say these days. Always pay attention to the little details.

It makes a big difference and people notice, even if they don’t say anything.

5. Learn to accessorize

Men, unlike women, don’t have much to work with when it comes to differentiating their look. Women have much more freedom to experiment with looks and styles.

At the same time, these limitations can be a good thing.

Use them to your advantage by choosing things that are slightly outside the boundaries of what you’d typically see and wear.

This helps push forward your own style, as well as give you a signature piece.

colonel littleton leather cinch belt

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This cinch belt is a great example. Tan leather belts, especially when worn with shoes and boots of a similar shade, aren’t that out of the ordinary.

But when you have a unique latch system that fastens the belt, and a unique way to adjust the sizing to fit your body, that’s something you don’t typically see.

There’s no need to go crazy. But a set of tasteful accessories, especially when they’re unique and long-lasting, goes a long way.

6. Bonus! Have confidence, or fake it ’til you feel it

Honestly, confidence (or lack thereof) is simply a state of mind, and faking it ’til you feel it works.

Let’s say you feel slightly insecure being at a party where you know no one. Or wearing a new sport coat and you’re unsure if the pattern is you.

You dwell on it a bit too much. Then you wonder if it’s obvious that you’re uncomfortable. Your confidence dips, which makes you feel even more insecure, and so on… it’s a vicious cycle.

Imagine if you flipped that whole scenario on its head.

You tell yourself: Yeah, I don’t know anyone here, so I’m gonna force myself to get acquainted with people. I’ll approach small groups and introduce myself enough times until it feels natural and normal. Here’s what I’ll say…

Or: No one but me knows I’m unsure about this sport coat. So let me just pretend I wear this thing all the damn time, like it’s a second skin. It’s so comfortable on me, I don’t think twice about putting it on!

This simple shift in mindset will quickly and easily translate into more relaxed energy and body language.

Trust me. I’m not the most outgoing guy, and I trick myself with this self-talk all the time. Give it a shot and let me know how it goes.

How do YOU stand out?

In the comments, tell me your favorite ways to stand out from the crowd.

Whether it’s a signature piece, paying extra attention to every little detail, or forcing yourself to wear things you wouldn’t normally – I want to hear from you.

Don’t forget, our friends at Col. Littleton are including a special gift with your purchase until 12/31/2016. Just enter “EffortlessGent” in the order notes on the checkout page.

Check out Col. Littleton’s awesome leather goods and accessories here.

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PUBLISHED November 24, 2016


Barron is a Lean Wardrobe Advocate and Founding Editor of Effortless Gent. He's from San Francisco but currently living in New York. Connect with him on Instagram, Facebook, Pinterest, Twitter, or Tumblr.