How Older Men Should Dress (Simple Style Advice Over 40)

There’s a lot of advice on the internet about how older guys should dress. If you’re a man in your 40s, 50s, or even older, what should you wear? Which mens fashion rules apply to you? Does your style have to change? Are you now required to wear dad jeans and cargo shorts?

The subject of menswear can get tricky as you age: your body’s changing, you get stuck in your ways, it’s harder to wear stylish stuff like skinny jeans or a graphic tee without feeling like you’re trying too hard or “dressing too young”.

But, really, it doesn’t have to be super confusing, especially if you follow a few style principles and create your own dress code that looks good and you’d happily follow.

In this article, we’ll cover those style principles with the goal of making sure you have a well-curated, sharp-looking, and age-appropriate wardrobe that works now, and for decades to come.

How should a 40 year old man dress, exactly?

Let me answer your question with another question: Have you seen the movie, Crazy, Stupid, Love?

If not, it’s an early 2010s rom-com that, according to Wikipedia, “…follows a recently separated man who seeks to rediscover his manhood and is taught how to pick up women at bars.”

What? That’s an awful one-line summary for an awesome rom com that was waaay more than that.

Anyway, Cal, a middle-aged, soon-to-be divorcé (played by Steve Carell) 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, swag-filled Jacob (played by Ryan Gosling, of course).

Ultimately, he 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. It was picture-perfect proof that guys, no matter their age, have no excuse for not dressing well.

Cal’s style (post-intervention) provides great examples of how the classic rules of clothing apply to any age group and never go out of style.

Which style category are you in?

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
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 are more comfortable in their own skin than guys in their 20s and early 30s, who are still figuring shit out.

Basically, you have the money and the self-confidence to dress better. So why aren’t you?

Style Tip: Ignore men’s fashion. Just follow these guidelines.

If you’re unsure where to start, why not follow in the footsteps of our friend, Cal? I can be your Jacob, making sure you don’t commit any age-(in)appropriate men’s clothing no-nos.

Let’s start with these guidelines and general principles:

Fit and proportion are the most important things

Lots of middle-aged / older men wear clothing that’s either too snug, or way too oversized. It could be that you’re wearing clothes that once fit (but don’t anymore), or you assume bigger clothes are more comfortable.

So, a few things about this:

1. Well-fitting clothing doesn’t mean “uncomfortable”
2. As we age, our shape and proportions can change, and to look and feel good, we have to wear clothing that complements those changes

Maybe you had a V-shape in your early 30s—wide chest and back, slim torso—but now, in your mid-40s, you’re not as muscular up top, and you have a bit of a belly. The clothes that fit you well back then won’t fit you comfortably now.

Maybe you were overweight when you were a younger man, but managed to drop the fat and maintain a slim physique all these years later… but you’re still wearing size XL shirts and your pants are falling off your waist.

Whether you’re skinny, overweight, or just right, you need to buy clothes that fit your current proportions.

But how do you find clothing that fits, exactly?

You have to try lots of stuff on. I know, it’s a chore, but that’s the only way to start understanding how clothes should fit.

Go to the mall and grab the size you think you are. Then grab one size up and one size down. Try them all on. Take a photo in the mirror. See what feels right. Bring a friend or your partner if you have to, and ask their opinion about how something fits.

Clothes should allow you the freedom to move without being oversized. It’s a balance.

If you prefer trying stuff on at home (I know I do), give Amazon Prime Try Before You Buy a shot. You can order a bunch of stuff, and they give you a week to try stuff on at home. Keep what you like, return the rest, and only get charged for what you keep. It’s pretty great!

Classic Casual Wear Over Fashion Trends

Fashion is a funny thing. Take the Dad Jeans trend:

• If a 22-year-old wears them, he’s trendy and fashion-forward.
• If a 44-year-old wears them, he’s frumpy and a terrible dresser.

Since you’re reading Effortless Gent, I assume you’re going for a modern version of classic style… a smart casual look with outfits that are a few notches above the jeans-and-sweatshirt default, while still being comfortable without feeling overdressed.

That sound about right?

If so, stay away from most trends and fashion-forward looks, especially if they’re an ironic play on “old man” style. Leave that experimentation to the younger guys.

So unless you’re a rock musician like Jagger or Slash, no ultra skinny jeans (a fitted pair of jeans is good, skinny, not good).

Unless you’re an eccentric movie star who makes questionable financial decisions like Johnny Depp, maybe chill with the scarves and limit your accessorizing.

For the most part, stick to neutral colors and more somber color schemes in general (looks more sophisticated in an outfit).

Great celeb style to emulate? Here are just a few examples:

Not sure if your jeans are skinny jeans? Wondering if you can still wear your favorite graphic tee? Thinking you have to trade in your casual sneakers for dress shoes?

Don’t panic. Keep reading. I’ll have suggestions for you later in this article.

Want awesome sharp, casual style? The Devil’s In The Details 👹

The classic casual outfit consisting of jeans, a T-shirt, and sneakers can be interpreted in so many ways.

The outfit can look sleek and polished, or it can look disheveled and frumptastic.

It comes down to the little details, like fit and proportion. Sizing. Color choices. Even quality and brand.

Dark Wash Denim > Dad Jeans

What defines “Dad Jeans”? The pair Cal is wearing at the top of this article is a good visual representation.

• medium or light blue (stonewash rinses)
• wide and baggy in the thighs
• too loose below the knee
• too long with fabric pooling at the ankles
• sometimes the opposite: hem is too short

The Levi’s 501 in your correct size is a good standard for denim. It’s a straight leg jean style that’s been around for decades. Find a pair that fits you in the waist, is a dark blue wash, and isn’t too long (little to no break… roll up the hem if you have to).

More resources:

• Five Ways To Wear One: Dark Blue Denim
• Dark Wash Jeans For Men: Top 6 Options, From Cheap To Investment-Worthy

The one pair I recommend to most guys who are average / bigger are the Levi’s 541.

They’re an athletic cut with plenty of room in the hips and legs, while still tapering nicely below the knee. You may have to size down 1-2″ from your normal waist size.

For example, I typically wear a 32×30 in most brands. In the 541s, I buy a 31×30 for a more classic straight taper, and a 30×30 if I want something more slim.

Simple, plain T-Shirt > Graphic Tee

I’m not suggesting you get rid of all your comfy tees. But if you’re going for a smart sharp casual style, keep the graphics to a minimum.

There are different levels of coolness and acceptability as well.

Free T-shirts are a hard no (“Liquor? I hardly know her,” while hilarious, only works if you’re a college frat bro). But a tasteful, vintage-looking design can work.

How do you know for sure? You have to develop an eye for good style, as well as a certain taste level. It comes with time and repeated exposure.

For now, if you’re unsure, a plain, well-fitted T-shirt in black or charcoal grey always works. Uniqlo makes incredible, affordable tees that fit well. I’ve been wearing plain J.Crew tees for many years. And Everlane is a more recent favorite for nice plain tees.

Sleek, minimal leather sneakers > bulky, cheap athletic shoes

You know the type of shoe I’m talking about. The Dad sneaker style is ubiquitous.

They’re a bulbous, chunky (not in a fashionable way) white and navy sneaker. Costco’s Kirkland Court Classic. The Nike Air Monarch. Some house brand from Payless or JcPenney.

Again, a darling of ironic fashion-forward 20-somethings, the Dad sneaker worn by a man who is of actual Dad age isn’t cool, it’s something to avoid.

Stick to a minimal low-top leather sneaker, free from obvious branding or design elements. The great thing about minimal leather sneakers? They’re age- and trend-independent, meaning they’re as appropriate for a 20-year-old as they are for a 60-year-old.

A Shopping List For The 40+ Year Old Men’s Fashion Beginner

This list of men’s fashion essentials for the 40+ year old assumes you’re going for a modern interpretation of classic style. A smart, sharp, casual look, similar to business casual. Not too casual, not too formal, but just right.

Also, this isn’t an exhaustive list—it doesn’t include anything hobby-specific (like hunting gear) or activewear (for working out, playing sports)—but will definitely get you started if you just need the basics.

At the same time, use your best judgement. Like if you live in Florida, you may want to trade the winter coat for a few pairs of shorts, and so on.

The idea here is you want fewer clothes (less decision fatigue), but better clothes (higher quality, longer-lasting, more enjoyment while wearing).

Here’s your list of staple pieces:

Pants

• Dark blue jeans (see this article)
• Charcoal grey or dark khaki chinos (see this article)
• A pair of mid-grey wool trousers / dress pants (see this article)

Shirts

• A handful of plain T-shirts in grey, black, navy, and / or white
• 2 oxford cloth button down shirts (OCBDs), white and light blue are the most versatile (see this article)
• 2-4 casual button-up shirts (any color / pattern can work here, but stick to menswear neutrals if you want to be safe)

Midlayers

• Midweight merino wool or cashmere crew neck or V-neck sweater
• Jersey cotton crew neck sweatshirt
• Quilted vest (see this article)

Shoes

See this article on the essential pairs.

• White or neutral minimalist sneakers (see this article)
• A pair of boots – suede chukka boot, leather work boot, and/or chelsea boots
• Tan leather loafers (see this article)
• Brown brogue lace-up dress shoe

Jackets

See this article on the different types.

• Parka or puff coat (see this article)
• Charcoal peacoat or overcoat
• Harrington style jacket, leather jacket, bomber jacket, denim jacket, and/or field jacket

Formal

• Single-breasted navy suit, white dress shirt
• Tan / brown plaid sport coat / blazer
• 1-2 ties in navy, forest green, burgundy. Prints encouraged
• Pocket square; go with white if you’re unsure, but prints are encouraged

Beyond that list, I think you can handle the rest, such as underwear, socks, baseball cap and other hats, scarf and gloves, etc.

Feel free to make substitutions based on your specific situation. This is simply a boilerplate list to help you get started.

For example, if you live in a warm climate, maybe you swap a the long sleeve collared shirt for a polo shirt. Maybe you go with a lightweight pant fabric, like linen, instead of a heavier cotton chino. If you rarely, if ever, dress up, maybe trade dress shoes for driving shoes or boat shoes.

Say you prefer suede shoes instead of all leather shoes. That’s fine, do a swap. Like a grey leather sneaker instead of a white sneaker? Sure! Swap it. Maybe it’s really rainy where you live, so you’d prefer a trench coat instead of a pea coat. Do it! Do the swap.

Casual style vs formal style: It isn’t either-or

One big tip: don’t think of your clothes as only formal, or only casual. You want to mix your casual clothing with your more formal clothing to create a “High / Low” look.

Having a High / Low look allows you to get more use out of your formal stuff, and the dressier items can elevate an otherwise casual item to appear more dressy.

Mixing your formal (high) clothes with your casual (low) clothes results in a smart, sharp look that is perfect for most places you go during your week.

One classic High / Low outfit: dark denim, white collared shirt (OCBD or dress shirt), navy sport coat, brown loafers. Easy to pull off, looks sharp, and you’ll never look too dressed up or dressed down.

Getting older doesn’t mean you should stop caring

Aspiring to dress well isn’t vain.

Dressing well is about self-respect, self-worth, being proud of yourself, and presenting yourself in an appropriate manner to those around you. It’s about feeling good and holding your head up high.

You feel more confident wearing a good-looking outfit, and you can accomplish more when you look good and feel confident. Can you do that in a worn out T-shirt from 1987 and baggy sweats? No, you can’t.

You don’t need to spend a ton of cash to have great style, by the way. Huge misconception. You also don’t need thousands of items in your wardrobe, as evidenced by my curated list in the section above.

You only need a few pieces versatile enough to be easily worn with each other. Start with that list above. I picked specific things that I’m certain work well together, and with anything else you might buy in the future.

Layering is your secret weapon

Knowing how to layer clothes has a double benefit: keeping you warm and adding visual interest to your look.

Let’s say you’re a month or two into autumn, and as you’re getting dressed, you put on your dark blue denim, a grey v-neck undershirt, a light blue oxford cloth button down shirt, a merino wool sweater, and your field jacket.

You realize after being out for a few hours that it’s warmer than expected. So what do you do?

Simply peel off a layer (like the sweater, or the jacket). Once it starts to cool down again, you can easily throw that layer back on.

Contrast that with an outfit such as jeans, a T-shirt, even though it’s too cold for just a tee. You’re either sweating in your parka, or freezing in a tee.

Layers are key.

Apply these helpful tips to improve your style today

To be honest, these tips work well for a 22 year old, a 44 year old, or a 66 year old. You can apply all of these, no matter your age, if you’re aiming to have a smart, sharp style.

Do these help? Would love to hear from you. Tweet at me or DM me on Instagram.