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.

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24 Responses

  1. Ethan Doan on

    what i like about this article is its powerfully simple.

    When you really break it down price wise it doesn’t cost that much to look great.

    Alot of these items can be had via outlets, sales specials etc.

    • Barron on

      Thanks Ethan, and you’re right, it really doesn’t cost much… it just requires a bit of effort and care.

      Even if we do spend a larger sum on, say, a great quality sport coat… it can last for years and is worth the investment for such an easily interchangeable, highly used piece.

  2. Bathacker38916 on

    Would someone please post a link to inky blue jeans in a 42×32 or 42×34 sizing.
    My local stores only have the dad jeans in these sizes.

  3. Online Subscriptions on

    I agree with everything in this article except for the advice on specific shoes.

    I haven’t yet reached 40, but I know that I will never ever wear shoes that most american men seem to wear – shapeless, overly round and overly wide. Everyone I asked says it’s comfort, but I think it’s more of a same story as with dad-jeans. Comfort and style should go hand in hand.
    I think there are a lot of great looking shoes in the $125-175 price range. I personally don’t like wingtips and prefer plain oxfords, like Cole Haan Men’s Air Colton Oxford. But that’s just me. Just don’t be afraid to try a slimmer looking shoe or one with a bit more pointier front. Don’t buy something just because everyone at work is wearing it. Be different.Another thing I would recommend is to buy quality shoes and treat them well. Buy 2-3 pairs that you really like and that would last you many years. It would save you a lot of money in the long run. And spend some money on some shoe care products (creams, leather honey, brushes, shoe trees, shoe horn) – they don’t cost that much, but would greatly improve your shoe life and looks.

    • Barron on

      Nice points re: finding a long-lasting, good-looking dress shoe. I wouldn’t say you’re disagreeing with me, you’re just addressing leather dress shoes while I pointed out some of the more casual options (top siders, desert boots, etc.), so great comment.

  4. Richard Jackson on

    I’m in my late 40’s and started dressing better after reading blogs like yours and some others who’s advice I trust. It’s interesting how other men behave around you when your at a function (i.e. kid’s school play) and they’re dressed for washing the car in the driveway and I arrive in non – Dad jeans, black and tan saddle oxfords and a fitted polo shirt. The looks you get from the other moms are priceless. I heard one woman ask her guy “why don’t you ever dress like that”. Just because you’re middle aged, doesn’t mean you should give up trying to look your best. Others do notice your appearance. Take care all..

    • Barron on

      Hey Richard, thanks for reading (and more importantly, applying what you read). I imagine the responses you get are amazing, just as you described, and I bet that feels great! It makes me wonder why more dads don’t try. Thanks for your comment.

  5. Ed on

    Hey Barron,
    Just started following your blog. Great articles!
    I’m 55 and I’ve been trying to improve my look for some time now. I have a somewhat unusual situation. I’m an advertising photographer, so many of the dress casual sort of looks are too formal for me. On the other hand tee shirts and jeans, (apparently the official uniform of southern CA where I moved to from NYC recently), seem too sloppy for a 55 year-old. Any suggestions? Looks I see either seem to young or too old.

    For the record, I’m 5’9″, 140lb, have my hair, and most think I’m about 40 or so.

    Thanks for your thoughts!

    • Barron on

      Hey Ed,

      LA is relatively nice year round. If I were you, I’d go with Polo shirts instead of T-shirts, and some nice dark denim. I know LA is super relaxed in their dress, but don’t get sucked in.

      You can do the casual sneaker (something like Jack Purcell Converse, Superga, Vans, etc.) which I think is pretty standard. Or you could pick up a pair of boat shoes or driving shoes (check out the Yes section here:

      If you want to wear long sleeves, you can get away with a slim fitting oxford cloth button down shirt, something from Brooks Brothers (pick up the Extra Slim fit, since you’re a slim dude), or the oxfords from J.Crew. You can wear them untucked with your sleeves rolled up, and still look better than 95% of dudes in LA.

      Fit is really the most important thing. Focus on getting a good fit in anything new you buy. Hope that helps.

      • Ed on

        Hey Barron,
        Thanks for your reply!Polo’s are my usual go to shirt, but I’m sick of them and have trimmed myself down to black and navy. I like the oxfords suggestion though.As much as I love the look of Purcells, they hurt my feet due to a ruptured achilles tendon from years back, (try to never do that…). Are Adidas Stan Smith’s an acceptable alternative? I think I may have seen them on our no-no list.  I’m trying to move away from sneakers entirely. Desert boots ok? My usual go-to footwear are a pair of Vibram soled Clark Luganos,  I think they look fairly neat and I can stand in them for twelve hours.Thanks for reminding me about the fit. Trying to find any shirt that doesn’t look loose is a feat.AOM, had a good article on building a wardrobe, with a list for creative types, though it a little bit too proper for west coast. I’d love to see your take.Thanks again for your time and help!Best,Ed

  6. Kevin on

    Out of curiosity, why gray color V-neck t-shirts? I assume you mean to wear them as undershirts. Is this incorrect? Great article, btw. I’m in my early 40s and only now starting to pay attention to what I am wearing. Sad, but true. 🙂

  7. Darrin on

    Dressing well seems like it must be so much easier when you don’t live somewhere very hot & humid for most of the year! I’m trying to avoid second degree burns getting into my car and heat stroke walking into work – yet all the pictures of style show a guy layering a sweater with a blazer!

  8. Darrin on

    Dressing well seems like it must be so much easier when you don’t live somewhere very hot & humid for most of the year! I’m trying to avoid second degree burns getting into my car and heat stroke walking into work – yet all the pictures of style show a guy layering a sweater with a blazer!

  9. Kevin on

    Just started reading the site. Really good. I just got 2 pairs of tailored dress pants, and a tailored grey sport coat. This stuff is addictive. I’m now on the lookout for brown leather dress shoes. I love Johnston & Murphys. Are they not dressy/quality enough?

  10. eaglesgift on

    Being as this article was written nearly three years ago, are the items mentioned still a good choice or has fashion moved on? I’m a bit of a moron when it comes to choosing clothes so any advice would be much appreciated.

    • Nick on

      Fashion has moved on, but style didn’t. The items that Barron writes about in this article are timeless and classic pieces. This being said items you bought like the ones in this article will look good new but they’ll also keep looking good the year after and the one after that. Choosing clothes is fairly easy. 3 things i’m always looking for in any clothes: the fit of the item, how I can pair it with my wardrobe and ofcourse will I be able to wear it 2 years from now and will it still look decent. Like for example most of the shirts i have are button downs in neutral colours or with some print on them(Gingham, stripes, etc…) those things pair well with all my trousers and looks good for years to come. Don’t give in to the trends, some trends are nice and sweet to buy, other are totaly ridiculous and will only be worn by hipsters and they’ll only be wearable for maximum one season.
      Hope this information helps a bit.