What NOT To Wear If You’re Over 40 | Style Tips For Older Men

As we discussed in our previous video about Dressing Well When You’re Over 40, style and confidence as you age is all about embracing what you have and presenting a classy, refined look. Now, it’s worth mentioning that nearly all of our style advice, from Essential Wardrobe items to Fit Guides, applies to all age ranges. But, dressing well later on in life is just as much about what NOT to wear as it is the exact items you are wearing.

So, we thought we’d answer a few of the most commonly asked questions about what not wear if you’re over 40.

 

Q: Can an older man wear white sneakers?

A: Absolutely they can.  In fact, we did a whole video about it.  White sneakers like Adidas Stan Smiths and are a classic casual item for any man, regardless of age. That said, if you’re not comfortable wearing white sneakers or you feel like they’re a bit too young, we recommend going with a nice, clean leather sneaker in any color of grey or navy blue. Suede versions are excellent too as the added texture is a nice look.

Picks:

Common Projects

Koio

Beckett Simonon

 

Q: Is it really important to wear fitted clothing?

A: Yes, it’s critical to wear well-fitting clothing, no matter how casual or dressy. That said, this doesn’t mean tight! There is a HUGE difference between slim, well-fitting, clothing that’s proportional to your body type and something that’s overly tight. A lot of older men end up skewing overly large or baggy due to comfort or fears that they aren’t dressing their age but having a wardrobe that fits you well is something every man should have, regardless of age. For mode insight, make sure to check out all of our fit guides for in-depth info on all types of clothing items.

 

Q: What can I do to give my wardrobe some personality?

A: The most simple and cost-effective way is the right choice of accessories. So watch bands, ties and pocket squares, a ring, or a fun patterned sock are all great ways to add a bit of personality in an age-appropriate way. Being age-appropriate is the key thing, and over-accessorizing is a quick way to kill your style by making it look like you are trying too hard.

 

Q: What items should I avoid if I’m over 40?

As we mentioned in a previous video, leather jackets are a big one for men over 40 to avoid, with one exception. We do like leather or suede bomber-style jackets for men in this age range, but other types like moto and biker-style jackets just make you look like you’re having a midlife crisis. T-shirts with logos are another huge no-no, they just make you look juvenile. Additional types of t-shirts to avoid include henleys and deep v-neck t-shirts. They just aren’t the right look for an older guy. Stick to polos and well-fitting crewneck t-shirts. On the denim side of things, jeans that are light-wash, or ripped and distressed fall into the same category, they just look too young. Keep your jeans well-fitting and in a dark wash.

 

Do Women Care How Much You Spend On Clothes?

One of the most common comments we see and hear time and again is “Women only care about men who spend a lot on clothing.” Now we believe that style is made up of a lot more things than just the clothes you wear and we talk a lot about how to build a stylish essential wardrobe on any budget. But, it is a fair question to ask.

So do women care how much you spend on clothes? Tune in and find out what we think!

Style and money are unrelated

Fit, and to a lesser extent, materials, denotes how “rich” you can look. You can be wearing a $5k suit but if it fits poorly and isn’t properly tailored, you’re still going to look like crap. But if you’re wearing a $500 suit that’s tailored perfectly and fits your body type well, you’re going to look like a million bucks. Dressing well in clothes that fit you isn’t expensive. Dressing poorly in designer clothing is very expensive and a complete waste of time and money, not to mention, no women will care if your suit is expensive if you look like a mess in it. Since we’re talking about fit, we’ve got Fit Guides for everything, so don’t forget to check ’em out!

Designer Doesn’t Always Mean Good

Covering yourself in designer labels to show how much you spend on clothes actually just shows a lack of class and tact. Wearing a $500 Gucci T-shirt is silly for two reasons: one, they’re knocked off so easily that often people assume it’s fake anyway, and two, did you really just pay $500 for a $2 shirt with a Gucci logo screen printed on it? To women, it makes you look like more of a sucker and its incredibly off-putting. Looking good is about the details and subtlety – women pick up on these more than most men know. 

Dress Within Your Means

We mention it a lot around here but it bears repeating, style is achievable at literally any budget. If you’re spending more than what your means allow on your clothing, that’s an instant alarm to a woman. It shows you’re either insecure or irresponsible financially. Either way, very unattractive. Be honest about your budget and stick with what works for it, it’s a much, much better look. Don’t believe us? We’ve got recommendations for budget-friendly denim, chinos, and more.

Dress For The Situation

If you’re wearing expensive clothing, but it’s inappropriate for the situation, women will be repelled. Wearing your brash, iced-out Hublot watch to a black-tie affair is just gauche. Flashy shows of money like this are inappropriate and they send up red flags like “insecure”, “ignorant”, “tacky”. Subtlety and class are infinitely more important to women, even when they don’t know it. EVERY woman, regardless of who they are, would jump James Bond’s bones because he’s subtle, confident, and elegant in his style. Remember that. 

The Verdict: Absolutely Not

Take it from a woman (and an incredibly accomplished one at that), the right women care about so many things that aren’t money and how much of it you spend (or pretend to spend) on your clothing. Style is about so much more than just what you wear and women know this. Style can be achieved no matter what your budget is, even if it’s zero, so don’t forget that!

 

How Much Should You Spend On Clothes?

As we always discuss, the right mix of items in your Essential Wardrobe is key in giving you the foundation to dress stylishly no matter what the occasion or your age range.  The great news is, it doesn’t matter what your budget is, you can build a stylish wardrobe no matter much you have to spend. 

Yeah, we know, many people often complain that you “need a lot of money to dress well” but that’s just not true.  It does take some proper strategy to know where and how to spend your hard-earned money though, and that’s where we come in. Figuring out where to save and splurge on items is a question we get asked all the time so in this edition of 2 Minute Tuesday we’re giving you our advice on how much money you should spend on clothes!

 

How Much Of Your Budget Should You Spend On Clothes?

Good news, this is simple: it doesn’t matter! Figure out what you’re comfortable with, no matter how much you have, and stick to that.  There are stylish options for everyone and every budget.

 

What To Invest In?

Both of us agree that dress shoes / boots and outerwear (jackets, peacoats, bombers) are the two places that it’s worth it to invest in.  Quality items in these categories will give you many years of wear and style.  Ashley also believes that if you dress up every day, or very frequently, it makes sense to invest in quality suits and blazers.

 

What To Go Cheap On?

Outside of the previously mentioned items, both of us agree that you can go much more budget-friendly on t-shirts, jeans, chino pants, and button-ups.  These items are easily replaced at any price point and will look sharp no matter how much you spend, provided you’re shopping smartly.

Our Favorite Podcasts? / Best Podcasts 2019

Just like a ton of you out there, we love a great podcast.  Whether we’re in the car, cleaning the house, or just taking some time to ourselves, they’re a great way to learn, be entertained, and get motivated.  Recently a viewer asked us what some of our favorite podcasts were so we thought we’d share some of our go-tos, for entertainment, business, and more.

In this episode of 2 Minute Tuesday we’re running down a list of our favorite podcasts and why we love them so much!

 

Dorian’s Favorite Podcasts

Dorian loves a mix of history, business, current events, and entertainment in his podcast diet.  Here are some of his favorites.

Conan Needs A Friend

A hilarious and insightful interview pod hosted by Conan O’Brien and featuring great guests like Dana Carvey, Bill Hader, Jimmy Kimmel, and more.

The Rewatchables

Part of The Ringer’s awesome podcast network, The Rewatchables recaps classic action, comedy, and thriller movies in a really funny way.  if you’ve ever found yourself on the couch on Saturday or Sunday afternoon watching movies like Step Brothers, Bloodsport, Top Gun, and really wanted to discuss how perfect these movies are, this is the pod for you.

Revisionist History

A great deep dive into notable historical and current events but with a unique perspective, this educational and entertaining show is hosted by Malcolm Gladwell, the brilliant mind behind such classic books as “The Tipping Point“, “Blink” and “Outliers“.

The Daily

Dorian loves the mix of important news stories and outstanding news stories from The New York Times editorial team.

Slow Burn

Dorian has mentioned his love for history, and in particular, presidential history and this killer series has seasons on The Watergate scandal and the Clinton/Lewinsky affair.  We’re definitely excited about Season 3, which will cover the murders of Tupac Shakur and The Notorious B.I.G.

Economist: The Intelligence

Another current events podcast, this time from The Economist, it offers excellent business coverage as well.

Revolutions

Another podcast for you history nerds out there, this one focuses on some of the most important and, well, revolutionary revolutions in history.

Seincast

Dorian’s love of Seinfeld is deep and strong, so obviously he’s going to be into this hilarious podcast.

Batman – The Animated Podcast

An offshoot of the awesome animated series (definitely not for kids), this serialized podcast is super entertaining and a must for all comic book fans.

 

Ashley’s Favorite Podcasts

Ashley loves true crime, technology, and some interesting non-fiction in her podcast menu.  Here are her go-to’s.

Reply All

Not so much a technology podcast, rather, it’s more about human stories with bits of tech, social media, and communication within it. We also love the great rapport between the two hosts.

Criminal

Ashley is a huge true crime fan, so this one is right in our wheelhouse.  Sure, it’s probably obvious that this one is about crime and criminals, but the stories are crazy and out-of-the-ordinary in a really entertaining way. Guaranteed to blow your mind!

Couples Therapy

A podcast with Casey Neistat and his wife, Candice, this podcast is pretty raw, unfiltered and a really interesting look into their relationship (and all relationships, really).

How and When Should Men Wear A Tie?

Ties are a fundamental accessory in a man’s essential wardrobe, they can add personality, elegance, and formality to many types of looks, no matter what your personal style is. Rules about style and formality, in both work and social settings, are changing so quickly that it can be tough to know when you should and shouldn’t wear a tie.

So, in this episode of 2 Minute Tuesday we’re discussing when and how men should wear a tie! For a full breakdown on our favorite ties and specific tips, make sure you check out our tie article!

 

With What?

A key thing to remember about ties starts with what you should be wearing them with. Dressier looks like suits and sport coats are definitely options you can and should wear a tie with. For more of a hybrid look, try wearing a tie with a bomber jacket, it can give your casual look a cool dressy vibe. One word of warning though, you don’t want to wear just a tie on its own without a jacket, it just doesn’t look right.

 

With What Types of Dress Codes?

When to wear a tie can also be determined by the dress code or how formal your place of work happens to be. Dress codes like “Formal”, “Cocktail Attire” or “Cocktail Party” often call for a suit and a tie. Business casual tends to lean slightly more casual but a tie can be appropriate given the right scenario. One tip we love, try a knit tie in those less-dressy situations, they’re not as dressy as a silk tie and will give your look a cool vibe.

If you aren’t totally sure about dress codes, ultimately you want to go with the crowd and let that dictate when a tie is appropriate. Always being stylish and a bit more dressed up is a great thing most of the time. But, you don’t want to be significantly overdressing for occasions or workplaces that don’t call for it. It can seem like you’re trying too hard or attempting to stand out, and not in a good way.

Don’t Iron Your Shirts!

Proper clothing care and storage is something we talk about a bunch, and for good reason.  Taking those few extra steps to properly care for and prepare your clothes are going to add an extra layer of both style and longevity to your wardrobe. In this week’s 2 Minute Tuesday we’re answering a great question about how to iron a shirt.  Tune in, the answer may not be what you think!

 

Why?

We firmly believe that men should be steaming not ironing their shirts.  Why? A few reasons:

  1. It’s quicker and easier – You’ve got to set up the board, get all those weird angles and spots, it’s a lot.  Whereas a steamer is much faster and way easier, a few runs from top to bottom on the front and sleeves and you’re done.
  2. It’s better for your shirts – Ironing is tough on shirts and its easy to look away for a minute or use the wrong setting and damage or burn delicate materials. Trust us, an iron burn isn’t a good look! The steam is much more delicate on non-cotton or blended fabrics.
  3. It’s more effective – The steam also does a lot better job of releasing tough wrinkles and creases than a standard iron or even a steam iron.

 

Our Steamer Picks

Whether you choose a handheld version or a full stand size, these are our two favorites.

Our go-to steamer

A full-size stand steamer

 

How To Steam A Shirt

As we mentioned, it’s super easy and effective.  Here’s how:

  1. Hang up the shirt
  2. Steam the front from top to bottom
  3. Steam each sleeve from top to bottom

That’s it!

We Sold The Company!

In this week’s 2 Minute Tuesday, we’re changing it up a bit and covering a question for Dorian! As a successful entrepreneur himself, Dorian has a lot of experience in the business world and starting and building companies.  So, in this episode, he’s going to answer a question about some of his favorite business and entrepreneurship tips and what it takes to build and sell a successful company.

Don’t forget to check out his business book recommendations below!

 

Read The 4-Hour Work Week

A classic book by Tim Ferriss, this book is packed with solid tips and an excellent framework for creating successful businesses in the modern entrepreneurship world.  Check it out here: The 4-Hour Workweek

Use Ignorance / Youth as a Strength

Part being humble and part being resourceful, your ignorance and inexperience can actually be an incredible tool when starting or growing a business.  People will often offer help, insight, or advice if you approach your interactions and, more importantly, mistakes, the right way.  If you approach business in a cocky or overly-confident way it can often work against you and you’ll miss out on valuable growth and insight.

Try and Test Everything

One of the mantras Dorian loves in the 4-Hour Workweek revolves around constant testing and experimentation.  You always want to use feedback, data, and trial and error to constantly evaluate where you’re at.  You can’t be afraid to try new things, adjust, and re-evaluate both success and failure (more on that in a second).

Fail Quickly and Often

Part of the trying and testing is failing.  It’s a huge part of not just starting businesses and being an entrepreneur but also success in general. You can’t be afraid to fail, start over, or abandon things that aren’t working.  It’s called “trial and error” for a reason, and often times your failures and what you learn from failures are the most important part of future success.  From Elon Musk to Jeff Bezos, no successful entrepreneur or business owner has ever gotten anywhere without failure, so embrace it, get better, and move on.

Cut Expenses / Mitigate Risk

As you get into starting a new business or work on a new idea you never want to bet your current financial future too heavily.  So, it’s important to consider the risk and mitigate potential loss at the beginning with thoughtful planning.  Look at approaching your life and business with low overhead and you’ll have more flexibility and less overall risk as you develop your business or company

 

Dorian’s Favorite Business Books

The 4-Hour Work Week

How To Win Friends and Influence People

Rework

Do You Do It Or Does It Do You – Lecture by Alan Watts