After college, it’s an interesting time. You don’t feel like an adult yet, but you’re suddenly in an adult world.

Real job, real bills, no more safety net…

And while much has changed, much hasn’t. You’re still the same guy you were before.

In many cases, you still have the same college wardrobe.

So many younger guys write me and say: “I want to be taken more seriously at work and by women.” Yet they don’t look in the mirror.

It’s not that they completely ignore their clothes.

They might focus on getting a few suits, some ties, maybe even a pocket square…

But they don’t pay attention to their everyday wear, which can often make a bigger difference to their overall look–especially if they work in a more casual office environment.

obl-finalThis post was brought to you by Old Bull Lee, the finest men’s shirts and shorts. Fabrics from France & Italy made with quality and soul in America.

What Holds Men Back from Dressing Better?

One reason some men are slow to transition away from their college wardrobe is simply “aesthetic inertia”–men are creatures of habit.

As my friend Tanner from Masculine Style points out, if you’re like most guys, you’ve probably had the same bank account or insurance company for years–and usually they’re just a legacy of something you set up years ago without much consideration.

dress like the man you want to be quoteOur clothes are no different. As Tanner notes, “the appearance of most men is rooted in passivity, not proactivity.” We just do what we’ve always done.

The other thing that holds young guys back from dressing better is the fear that they will look like their dads:

They know they are officially grownups, but if they start dressing the part, maybe their friends or coworkers will call them out for being someone they’re not. Of course, this rarely actually happens.

Right or wrong, clothes tell a story. If you want to continue dressing like an overgrown teenager or college student, that’s your decision. But if you want to be taken more seriously, you have to dress the man you want to be.

Here are 4 ridiculously simple tips for dressing like a grown man:

1. Elevate your Shoe Game

It may not be intuitive, but one of the easiest ways you can quickly upgrade your style is with your shoes.
While the rest of your outfit collectively speaks to what kind of man you are, shoes are like “shorthand” to quickly give someone an idea of what you’re all about.

Now that you’re a grown man, it’s time to ditch the sneakers with jeans look. Unless you’re exercising, you should not be wearing athletic shoes.

For your everyday wear, consider wearing some desert boots–they do a great job of spanning that “casual but not too casual” look. At the end of the day, your casual clothes should appear effortless, but that does not mean sloppy.

Another route to take is the good old wingtip–do the “high-low” look, where you’re mixing in a shoe that’s traditionally more formal with jeans. This can be a fabulous way to keep your everyday outfit still casual but smart-looking.

For Summer wear, if you’re used to tromping about in flip flops, consider rotating in some deck shoes or canvas lace-ups.

2. Embrace the Oxford Button Down Shirt

old-bull-lee-oxford-button-down-full-viewAnother guiding principle of building a grownup wardrobe is to spend your money on fewer, more versatile pieces of clothing.

The Oxford Button Down Shirt is precisely one of those “pillar” pieces to your wardrobe. Very few items are as versatile as this.

It can be worn with jeans, slacks, and even with shorts. Where before you might have reached for a more casual patterned sport shirt or a logo t-shirt, now you should start reaching for the Oxford Button Down.

It provides the everyday comfort you need to get through a hectic workday. But it also has the refined touches that make you look like you could be the boss, and not just an employee at work. Plus, it’s nice enough that you could throw on a sport coat and look right at home in a nice restaurant or cocktail lounge.

What makes a good Oxford Button Down Shirt?

Old Bull Lee does a great job with their new line of Oxford Button Downs. A good shirt–like many other things–comes down to 2 things: (1) the quality of the material, and (2) the quality of the craftsmanship.

Many shirt manufacturers cut corners by using substandard fabrics and farming out assembly to offshore factories. But after talking with Old Bull Lee owner Lee Johnson–a former architect turned garment maker–I get the sense his company doesn’t do anything the easy way.

closeup of oxford button down collar

Old Bull Lee uses high-quality “long staple” cotton from Thomas Mason, which is considered by many to be one of the top Italian mills for dress shirt fabrics. The 2-ply cotton gives the shirt a substantial, structured feel, but softens over time to feel like a second skin after repeated wearings.

Besides the material, the little touches are what make for great quality, like real mother-of-pearl buttons and single-needle stitching. And Old Bull Lee shirts are made right here in California.

Getting a few of these work-horse shirts in simple neutral colors like white and blue makes for tremendously versatile wardrobe–and can really elevate your everyday look.

3. Refresh the Jeans Situation

As far as everyday wear, jeans are becoming more and more common–especially as offices get more and more hip to the idea of casual dress codes.

The problem is, to many of us guys jeans are jeans are jeans….

We think, “great, it’s okay to wear jeans. I’m set!” But we don’t pay any attention to what condition our jeans are in or how they fit us.

Meanwhile, we have saggy butt syndrome where it looks like we could legitimately hide a football in the back of our pants; the denim is faded as all hell; and the distress and holes make it look like we’ve been mauled a la Leo in The Revenant.

More than likely, you have a few pairs of jeans, each at a different stage in their lifecycle. If you think of all your jeans collectively like a photograph, now’s the time to do some cropping. Get rid of the worn-out pairs (or at least put them aside for “yard work” or the rag bag). And keep only the jeans that fit you well.

Find some new dark-wash jeans that fit your legs and backside without leaving a lot of excess fabric. Also, consider getting some darker wash jeans with a little less distress. Fake scrapes, holes and faded fabric were fine when you were just a snotty nosed kid in college. Now that you’re a grown man, your jeans should look like you were able to buy them new rather than scavenge them from a dumpster.

Plus, the nice thing is, if you start with a darker wash with less distress, you’ll eventually add your own real distress and fading. And that way your jeans will also look nicer, longer.

4. Mix in a Sport Coat

A final strategy is mixing in a well-fitted sport coat. This is the crowning piece that really sets you apart as a smartly dressed man.

It goes without saying that a sport coat will be a major upgrade if your previous go-to for light outerwear was a hoodie or a nylon windbreaker–but you shouldn’t worry about it feeling too formal.

I used to think I’d feel self-conscious wearing a sport coat to work. But after I tried it, I realized no one batted an eye…except to tell me how great I looked.

There are many sport coats available these days that are less structured and designed with softer fabric, so it doesn’t feel like an awkward combo with jeans.

Keep in mind: sport coats were originally invented to be worn while watching or participating in outdoor sports–so they were always intended to be a “utility” garment for everyday wear.

Wrapping it Up: Dress Like the Man You Want to Be

If you haven’t noticed the trend yet, with all these tips you’re essentially mixing in slightly more elevated pieces to your everyday wardrobe. At first, you might feel like you’re dressed up, but before long these new components will feel just as comfortable as your worn out jeans, t-shirts and sneakers.

But outwardly, you’ll be sending a very different message about who you are: a grown man, not a boy. And not just that–a man who dresses intentionally, takes care of his appearance, and takes responsibility for his life. In short, a man in charge of his own destiny.


Old Bull Lee: We Didn’t Invent Confidence, We Just
Built the Clothes for It

man jumping up in the air wearing old bull lee shortsLong known for their iconic and stylish shorts, Old Bull Lee is now offering men’s button down dress shirts. Made from the best luxury materials available (Thomas Mason fabrics, Mother of Pearl buttons) and carefully sewn in the most respected shirting factory in California. Free shipping and Happiness Guaranteed.

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Credit: The Distilled Man


  1. Vincent Verdi

    Excellent, a home run, just like your post on texting .

  2. thanks Vincent!

  3. Kenneth Geathers

    Hello Kyle! I love this article! It helps men to truly express who we and the message we want to send.I find so many men dress like boys instead of like real men. In your message if you want to be taken seriously you have to dress better!

  4. Thanks Kenneth!

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