12 Steps to Dress Like an Alpha Male

An Alpha Male shouldn’t be consumed with how he dresses. He shouldn’t think about it, fret about it, or worry about it. He shouldn’t give meaning to clothes, garments, and accessories. A man’s meaning, his strength, comes from his principles and values and habits; it comes from who he is not how he looks or what he wears. However, to care about how you look portrays something entirely different: pride.

There is good pride and bad pride. Bad pride can lead to the fall. Pride can keep you from doing the dirty work necessary to succeed. It can lead you to leave opportunities behind because of a false and destructive view that you’re “above that kind of work”. Pride can be dangerous, but it can also be constructive and necessary.

There’s taking pride in one’s work, something that leads to a job well done and attention to detail. There’s pride in who you are which leads to greater effort, less time wasted, and audacity in the goals you set – if you think you’re worth more you’re going to act like you’re worth more and you’re eventually going to be worth more. An extension of this is pride in how you look.

Men once wore suits on airplanes. Clean-shaven, they’d walk with a head held high to whichever destination they were embarking to. Pride in how you dress is good, but worrying about what others think is cancerous and useless.

To reach this fine balance where you can dress well in under 5 minutes then walk out the door not giving a rats ass about what others think, you have to know certain basics; basics that we’ll cover in this article then set you off out into the world to not only be a bad ass and an alpha male, but look like one too.

Alas, we must start with a disclaimer of sorts.

Vanity and masculinity can’t coexist. If a man is too worried about what others think he can’t be true to his ambitions, they’ll be tainted by the wants and desires of others. From a fashion standpoint (fashion being a word I despise as it conjures up images of bony humans walking down runways – Victoria’s Secret runway’s being the exception) you have to find your style, and as a man it must begin and end with simplicity.

12 Steps to Dress like an Alpha Male

An alpha male is a leader. As a leader you can’t, once again, be fretting over the opinions of those you lead. Dress with a purpose. Dress fast. Dress simple. Dress in a manner that enables adventure, not in a way that prevents it.

Read that again.

What you wear shouldn’t keep you out of the arena of life, no matter the form this arena takes. It should bring you into it. Always treat your clothes as they are: fabric. Their value is a myth. It isn’t real.

Above all else, don’t pluck your eyebrows. Don’t shave your damn legs. Don’t ever lean toward the metrosexual look. Be a man. Dress like one. Give a shit about colors that match because everything in your closet should match. Take out a pen and pad and let’s get to it.

1. Start with the jeans.

Not an image of “how to dress”, but a picture of a fella wearing some fine jeans (Lumina).

When you’re figuring you how to dress, start with the clothes you’re going to wear most. This changes for some guys who spend a lot of time in suits and so forth, regardless, start with the clothes you’d want to wear most.

For most guys this single article of clothing that we wear most is our precious pair of jeans. Or pairs.

Choose them wisely.

A couple things you want to ensure with jeans:

a. They don’t fit perfectly lengthwise, you want a bit of length at the bottom of the jean, especially if you’re a boots-wearer.

b. Snug but not skinny. Skinny jeans are for hipsters. My goodness I can’t stand hipsters.

c. Buy a durable pair.

Buying a durable pair becomes even harder if you’re hitting the gym on a regular basis because jeans just aren’t made for guys with bigger thighs, they’re also not made with the same quality they once were. I remember my old man always telling me a good pair of jeans used to take 3 weeks to break in. ‘Tis a reality I was never exposed to until I got a pair of Lumina Jeans.

I wore Lumina jeans all over Italy (wearing them there on the right), and where most jeans start to wear in the crotch area, these guys are still going strong. They’ve become my only pair of jeans. I shall buy a second pair, but in the summer ’tis all I need.

2. Buy some nice, dull t-shirts.

Dull shirts? Yes. Shirts that you can throw on to go to the gym, beach, work, throwing the pigskin around with the fellas, and tee’s that go with jeans and shorts and whatever else you want to wear down there.

Buy dull colors first, then if you really want to, go brighter. But buy quality, that doesn’t mean spending a ton of money, just make sure they’re made with quality fabric and you’re good to go. Fill your closet with at least 10 tee’s. Dull greens and greys and reds and whites and blacks. Have them fit snug, ideally snug in the arms (although that’s more up to your training regimen than your clothing) and a bit loose in the body.

Note: Huckberry always has a great selection of shirts.

3. Now some button ups, but don’t get pretentious.

Standing atop il Duomo in Milan, wearing a fine button up.

Buy button-ups but go casual. Don’t start off with the jeans and white dress shirt and black dress shoes look. Actually don’t go there at all. Plaid with some red in it or another print with different colors is always a great place to start. A dull red, green or even a denim shirt is also a great choice.

I use the word dull a lot to describe the colors, the effect won’t be boredom, you’ll stand out as a human who knows what to wear without trying to have that “look at me” peacock effect.

Grab a couple of these. Here are some good examples: Adventure Apparel 

4. Add some color to the pantaloons.

Jeans should be first and last and everywhere in between. They’re the most durable and the most versatile pant a man can have. But a different shade of denim or even a kaki pant is also a great idea.

Light brown, beige, whatever floats your boat, just grab 1 pant that’s a little different.

In total a guy should have 3 pairs of pants. Anything more than that is clutter. You don’t need options. In fact, the fewer the better.

5. Two jackets is more than enough.

Buy a jacket that you can wear in the winter and another that you can wear in the spring. Make sure both go with the rest of your gear. And make sure it’s not a jacket that you fear getting dirty. Life is messy, dress accordingly. I have myself a cloth, navy jacket (the one pictured above) and a bigger, navy pea coat for the winters.

6. And now the Henley’s.

My favorite kind of shirt is the henley. That is, a tee shirt, 3/4 sleeve, or long sleeve waffle, the only difference between them and a regular shirt is the buttons at the collar. Buy a few henley’s.

Go heavy on the greys, but grab some whites and browns and multi-colors shirts if you’re going for the 3/4 sleeve. It’ll differentiate you from the rest of the t-shirt wearing crowd. Also invest in a couple v-necks. Don’t go too low with the v, you’ll look like a metro, but don’t go too high either, a nice, medium-depth V is perfect.

7. Boots of two sizes.

I have 3 pairs of boots, which is a bit much. Two is more than enough. I have a black, somewhat dressier pair, cowboy boots, and bigger, traditional boots that I can wear in the outdoors and in all climates.

Tip on boots, buy quality without breaking the bank.

For your main pair of boots, you can’t beat Thorogood Boots for quality and bang for your buck.

Every man should also have a pair of cowboy boots, for we never know when we’ll have to hop on a horse and charge after some injuns. For cowboy boots it’s tough to beat (the pair I picked up).

8. On Grooming.

Grooming is important, but not that important. The 5’oclock shadow is always good, and if you want to grow a beard have at it. My strength gains have increased by 25% with every new inch of facial hair I’ve grown and decreased at the same rate with every inch I’ve removed.

In short, beard = manliness.


Don’t shave your legs nor your arms. Don’t pluck your eyebrows, ever. Take care of your back hair if you like, trim your chest hair if it really gets out of hand, and keep your neck hair in order. Other than that, your hair style is personal, you know what looks best, as is facial hair.

9. Make it fit. All of it.

Buy quality. Don’t buy quantity. And make sure your clothes fit.

You may have to spend a bit of money, but it’s better to spend it once than to have to constantly buy new stuff because the old stuff wears out.

Invest in quality clothing and a tailor. Make sure he leaves some room. ALWAYS leave room, especially if you expect to put on some muscle mass in the near future, it sucks to buy something like a suit then have it no longer fit a couple months later (I’ve made this terrible mistake). But make sure your clothes fit snug and accentuate the V you’re working on building.

Invest in quality and find a good tailor.

10. The only accessory a man should have: a watch.

Every man should have a watch. Necessary? Hell no. It’s a thing, and no one needs things. But I like watches. Always have. And I don’t buy them frivolously, but as milestones.

If I reach a milestone in my life or business I may celebrate with a cigar, a nice bottle of scotch, or a watch. The watch thing has only happened once, since I bought a SevenFriday watch last month. So it doesn’t happen often.

Want to check out the watch? I “know a guy” – his instagram: @sevenfridaycanada – email if you’re interested in getting one: info@sevenfriday.ca

11. On suits.

Have one or two, or more if your work requires it, obviously. The most important thing is to make sure they fit and fit well. Site’s and companies like Indochino are making these tailored fits more affordable (if you know of any others, add them in the comments section). If you’re like me, and you’re only going to wear a suit on rare occasion, splurge a little, buy quality, and have something tailored for you rather than buying off the rack and making adjustments (which will end up costing close to the same price).

12. Do Your Thing.

Writing a post about clothing does, admittedly, feel weird. Talking about fabrics and style can take away from the mission, but if done in the right way, it can improve it. Hopefully we’ve accomplished this here.

With everything we’ve covered in the article, it’s important to do your thing and do it with confidence. Clothes won’t make you more confident. They can’t truly give you that confidence that aids you through tribulation. They can make you feel better and more comfortable in your own skin, though, so you may as well take pride in how you wear them.

But do your thing.

If you like the athletic look, wear more sneakers and shorts and dry-fit gear. If you like the jeans and boots, do that. If you like both, mix things up. Do your thing, have your style, and take risks. If you want to push the envelope, do it. Risk is always a good thing.

Note: Here’s a solid “style guide” for men –> How to Dress With Pride (video)

Most importantly…

Dress Like a Man Damnit!

If you want to portray the alpha you have within you, and I have no doubt that he’s waiting to be unleashed, then start dressing like a man. Men don’t dawn themselves in accessories, nor are they so worried about what they wear that they spend more time getting ready than a lady. Men wear simple clothes, fabrics that endure our lifestyle.

We don’t ever dress with a sense of vanity leading the way. How we dress conveys the pride we have but what we wear isn’t who we are. We could be wearing rags and the heads will still turn.

So if you want to dress like an alpha male you must first become an alpha male. Take this article to heart, but if you really want to walk with a purpose and with an impact, read this: How to Be an Alpha Male.