The other night, the girlfriend and I caught a late showing of Crazy, Stupid, Love. Steve Carrell’s character, Cal, is a middle-aged, soon-to-be divorcé who, in an attempt to pick himself up after days of self-loathing and pity, becomes inspired and then coached by a younger, smoother-talking, swaggerific Jacob (played by Ryan Gosling), and ultimately reinvents himself.

There was a montage during Cal’s reinvention that displayed him in some pretty impressive outfits for a guy his age and in his situation. This made me realize that guys, no matter their age, have no excuse for not dressing well. The movie is a great example of how the classic rules of clothing apply to any age group and never go out of style.

Most men ages 40 and up seem to fall into one of these three categories: 1.) they really get what they’re doing, 2.) they’re stuck in some previous decade they enjoyed most, or 3.) they stop caring completely.

Ironically, lots of men in this age group also have the level of success their younger counterparts are striving for, and most are comfortable in their own skin, which I assume comes with over four decades living on earth.

So for you older gents who are realizing you need to present yourself better, why not follow in the footsteps of our friend Cal?

Fit and proportion is still as important as always

I see lots of older dudes wearing really, really snug clothing, like they stopped buying clothes 15 years ago but their waistlines continued to expand. Or they wear really big clothes, often under the assumption it’s more comfortable.

Well-fitting clothing doesn’t translate to uncomfortable, and whether you’re skinny, overweight, or just right, you need to buy clothes that fit your proportions.

Stop lying to yourself. If you no longer fit into the pants you did five years ago, go buy a bigger size (or better yet, start exercising again). If it’s been a while since you’ve tried fitting yourself for clothing, go to a higher-end department store and ask for help from a knowledgeable salesman. That’s their job, after all, to assist you in getting this stuff right.

Alternatively, go to a store yourself and start trying on clothing. Grab several sizes in the same style, and see what fits best.

There are alternatives to the Dad jean

More like Gosling, less like Carrell

What defines a Dad jean? Well, the pair Cal is wearing in the picture to the right is a good visual represntation. Overly-washed light blue denim or “WalMart blue” denim, unnecessarily high rise, wide throughout the thigh and calf, and sometimes even a short inseam, causing unintentional flooding.

Levi’s 501 or 505 is a good standard for denim. If you find yourself in Dad jeans, please do the world a favor and go to Macy’s (or Sears, even) and pick up a pair. Denim enthusiasts will argue that Levi’s at Sears differ greatly from those at Macy’s, which differ from the ones at Urban Outfitters, which differ from the pairs at the Levi’s stores themselves.

Don’t concern yourself with that right now; you have bigger problems. Just snag a pair of 501s and move on with your life. Oh, and make sure they’re inky blue, unwashed, non-distressed denim. This will be your everyday pair.

Once you’ve scored yourself a new pair of well-fitting, non-Dad jeans, don’t just wash them like any old pair. Wash them separately or with other dark-colored clothing, and use Woolite Black to resist fading. Hang dry to avoid shrinking.

Better yet, don’t wash them until they’re visibly soiled or smell so bad your dog is offended. Seriously. Non-distressed denim tends to form to the contours of your body, so they feel more and more comfortable with each wear. Washing them is like hitting the reset button.

Shoes matter

Barring any medical complications, pay attention to your footwear. Don’t walk around in public wearing beat up Asics or Costco’s Court Classics tennis shoes. You’re a grown, established man.

Find a good pair of brogues; my favorites are the Florsheim Veblen. They’ll look great with your non-Dad denim.

Other alternatives? Tan Sperry Top Siders are classics and go with everything. So do Clarks desert boots.

If you’re a sneaker guy, go with something unadorned and simplistic, like a pair of low-top Jack Purcell Converse or Tretorn.

Stay away from anything designed for sports use (basketball shoes, running shoes, cross trainers)… those are only fine when you’re actually participating in said sporty activity.

Getting older doesn’t mean you should stop caring

Maybe you’re married and have kids, or you’re in a committed relationship, so you’re not on the hunt for hot chicks anymore. Perhaps you’re no longer trying to impress the dudes in your gang with your cool threads. Regardless, you should still be trying for your own sake. You’re a man! When you’re out in the wild, present yourself with some respect.

Dressing well isn’t just about vanity (at least not completely). Dressing well is about self-respect, self-worth, being proud of yourself, presenting yourself in an appropriate manner to those around you. It’s about feeling good and holding your head up high. Can you do that in a ratty tee from 1987, or your college-aged son’s old high-school clothes he no longer wears? No, you can’t.

Style isn’t about spending gobs of cash on the latest and greatest things from the runway, or about having a guest bedroom double as your personal walk-in closet. You don’t have to have thousands of pieces in your wardrobe. You only need a few pieces flexible enough that they can easily be worn with each other.

Not sure where to start? Work on this list:

1. 1 pair inky dark blue denim, unadorned, plain, non-distressed, unwashed (have I mentioned this enough?)
2. 1 pair tailored navy trousers
3. 1 white oxford cloth button-up / poplin button-up
4. 1 light blue or lavender oxford cloth button-up / poplin button-up
5. 1 navy blazer (gold buttons optional, vents + great fit + tailoring mandatory)
6. 1 casual two-button khaki sport coat
7. 1 charcoal gray 2 button wool suit (vents + tailoring mandatory)
8. 1 pair of brown leather lace ups (rounded toe, slim leather sole)
9. 1 pair of black leather lace ups (same)
10. assortment of dress socks (be daring and experimental with color)
11. 3-5 heather gray v-necks
12. boxer briefs (or briefs, but no regular boxers… too much material underneath your pants)

Don’t be scared to layer

Layering can add layers (clever word play! not really) of visual interest to your outfit. Another benefit? You can control your bodily temperature in gradual steps.

Let’s say you’re a month or two into the Autumn season, and you have an undershirt (hopefully a gray v-neck) over a button-up dress shirt, and then a thin merino wool sweater, and then a blazer as your outermost layer. Getting warm? Peel off a layer. Still hot? Peel off another. Starting to get chilly? Throw that layer back on.

How would you do that if you wore, say, a T-shirt underneath a winter parka? You’re either sweating in your parka, or freezing in a T-shirt. Layers are key.

These ideas apply to every man, young and old

If you’re insightful, you may have realized this. Doesn’t matter if you’re an 18-year-old high school grad coming into your own sense of style, or you’re 62 and running around the park with your grandkids… these basics can be applied in any situation.

What do you think?

Have you seen Crazy, Stupid, Love? What do you think about Cal’s new sense of style?

What other basic rules (that apply to any age) did I miss? Am I forgetting any must-haves in that starter list above? Let’s hear your thoughts below in the comments.

Got a question? Hit me up!

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