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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.

How To Dress Well When You’re Over 40

Just because you’re over 40 doesn’t mean you shouldn’t be giving some consideration to how you dress. While the majority of our style tips are applicable no matter what your age is, for you older guys out there there are a few extra things to keep in mind. Above all else, it’s about both embracing your age and confidence, and crafting a style and wardrobe that enhances everything you’ve got going for you.

Here’s how to dress well when you’re over 40!

Dress Your Age

The older you get, the more important it is to dress your age. There’s nothing sadder than an older guy trying too hard to look young. Embrace your age and all the great things that come along with it. We’ll discuss further in a minute but this doesn’t just go for the items you choose, it has to do with the fit and how you wear your clothes as well. It’s important to always strive for a tailored fit. In terms of specific items we recommend, suede bomber or collared jackets, wool or cashmere blend sportcoats paired with chinos, dark wash jeans, or wool trousers are all excellent places to start. You can easily dress these items up with a collared shirt and dress shoes or dress them down with a sweater or t-shirt and sneakers.

Stick To The Classics

Just like dressing your age, as you get older it becomes even more important to stick to classic, timeless items. Leave the trends to the younger guys and embrace the distinguished style that you can pull off. For example, some classic items that should be the foundation of your wardrobe are: suits /blazers, oxfords, dress boots, chinos, Harrington, bomber or standing collared jackets, and polo shirts.

Class It Up

Many men mistake getting older and trying too hard with dressing too casually. Yes, there’s always a place in your wardrobe for well-fitting basics, but take your casual wear up a notch. A polo shirt instead of a t-shirt works well, leather loafers or driving mocs instead of sneakers instantly adds class to a casual outfit. And if you want to add personality to your outfits more, that’s always done through accessories – not the main items in your wardrobe. Understated, distinguished and in-control is what we love to see older men doing. Screaming “Look at me!” with crazy outfits or “funny” t-shirts is just immature.

Nail the fit

We talk about it all the time and have an entire series dedicated to its importance, because, above all else, this is key. Many older men tend to wear clothing that’s one or two sizes too big to hide problem spots on their bodies or for pure comfort. Big mistake – it actually starts bringing attention to you hiding something and being insecure about it. Wearing-tailored clothing will always allow you to present your best self as opposed to wearing too tight or too baggy of clothing, which is just unflattering.

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.

Are Subscription Boxes Worth It?

Subscription boxes are everywhere these days and we always get a ton of inquiries about clothing and grooming versions. We definitely have some opinions on how good they are and whether or not they are worth your time and money.

So, in this episode of 2 Minute Tuesday we’re discussing whether or not subscription boxes are worth it!

The Answer: Nope, Not Worth It

Believe us, we see a ton of these, and they just aren’t worth your time or money (with one small caveat below).

Why?

There are a bunch of different types out there but ultimately the amount of stuff you get just is too much and not of good quality. Who needs new socks or skin cleanser every month? Nobody. We get that many of you are super busy, but we promise that the time you invest in learning how and what to shop for is well worth it. Since you’re reading this and watching our channel, your personal style is obviously a priority, and cultivating your own Essential Wardrobe is an important investment that’s worth your time.

That said, we do love and enjoy a bunch of the versions with consumables like snacks, coffee, wine, charcuterie, etc. Those are great as it allows you to try new things and ideally the items don’t pile up and go to waste.

How To Build A Wardrobe?

Building a wardrobe doesn’t have to be an overwhelming or daunting task, but it does take some strategy, especially when you’re planning out the right purchases. In this episode of 2 Minute Tuesday we’re answering a viewer question about how to build a wardrobe.

Should you purchase by outfit? Or buy items piece by piece? What’s the right way to expand your wardrobe and keep it stylish? We’ve got all the answers you need right here.

Start With Versatile Essential Pieces

The right way to build your wardrobe is by starting with individual, versatile basics that you can mix and match for a variety of different outfits. A common mistake a lot of guys make is to just buy an entire outfit or two right off the mannequin. While that might look great together, you’re not necessarily going to be able to break apart and combine that one outfit or two for other situations. Plus, you can’t just wear that one outfit or two for every scenario.

As we discuss in our Essential Wardrobe series, building a foundation with items that are timeless gives you flexibility to meet any situation and the confidence to know you’re always going to look stylish, now matter where you’re going. Items like dark wash jeans, chinos, basic dress shirts and oxfords, basic t-shirts and polos, versatile outerwear, and blazers are going to allow you to put together looks that are not only stylish but uncomplicated.

After Your Have A Foundation, Add Along The Way

Once you have build a solid, foundational wardrobe you can then start adding in those special pieces like a statement shirt or leather bomber jacket, additional colors and patterns, or one-off items. You can feel free to start adding in some more personality and seasonal items with confidence because you’re always going to have that solid base to fall back on.

Does This Apply To Me?

It may seem deceptively simple, but who does our advice apply to? We always strive to give our audience useful, practical advice about style, life, dating, and more, all from an experienced and thoughtful perspective. Whether it’s wardrobe tips for the season or advice on how to improve social skills, we always do our best to appeal to as broad of an audience as possible.

In this episode of 2 Minute Tuesday we’re diving into a great question about who should take our advice and why, so tune in and find out what we think!

Sexual Orientation Doesn’t Matter

Our life and style advice applies to all, regardless of hair color, body type, or sexual preference. We do our best to give our educated advice on style and life that should work for most, if not all people. Sexual preference is a highly personal subject to you and you alone, we’re just here to help you dress and live better, no matter who you’re into. So, you can take that idea out of the equation and just focus on it without the lens of sexual preference.

Essential Style Is Important, But Make It Personal

We always discuss the foundations of a timeless, Essential Wardrobe because it’s versatile and always in style. But that doesn’t mean you have to dress a particular way if it’s not you. Once you have the foundations of style built you can then add in your personal touches to make it your own. Like streetwear or “bad boy style”, your personal style shouldn’t feel like a costume or inauthentic, it should be a representation of your own personality, no matter who you are or what your sexual orientation is.

Why Older Men Shouldn’t Wear Leather Jackets

If you’re an older guy, dressing your age can be tricky. As we discussed in a previous 2 Minute Tuesday, there are things you should, and maybe more importantly, shouldn’t do as a stylish older guy. In addition to cultivating a timeless Essential Wardrobe, some items just don’t work. We’re revisiting some style tips for older gentlemen in our audience after some feedback and questions about leather jackets in particular.

They Make You Seem Like You’re Trying Too Hard

The style and bit of rock n roll edge that a leather naturally has just read too young for an older guy. There’s nothing wrong with having some cool factor in your wardrobe, but there’s a line where something like a leather jacket doesn’t help this, it just hurts it.

It Doesn’t Complement Your Age

At a certain point, we encourage you to embrace your age, whether you’re 40 or 70. This doesn’t mean dressing in a way that feels old or stuffy (no matter what your age is), but rather you want to cultivate a style that’s distinguished and age-appropriate. You want a look that doesn’t detract from your natural stylishness as an older guy.

There Are Better Alternatives

As we mentioned, there are a ton of better alternatives available for you older gentlemen. A bomber jacket in a different material like suede or cotton is a great place to start. You can also try a Harrington jacket for something equally as stylish.

Suede Picks:

Other Picks:

Does Well-Dressed Mean Boring?

We talk so much about an essential wardrobe and timeless personal style, it’s hugely important. A sharp timeless wardrobe is the foundation of great personal style and, ultimately confidence. This week on 2 Minute Tuesday we answer a great question from our reader/viewer Arthur. He asked, “Does well-dressed mean boring?”

Tune in and find out what we think.

Timeless and Classic, Not Boring

Hopefully, we can help you reframe your thinking that dressing in a classic, stylish way might be boring. Rather, it’s always appropriate and timeless. You never have to worry about being out of style or not being appropriately dressed, and you can feel confident that you’re always going to look great. Trends come and go at lightning speed and flash doesn’t equal substance.

Embrace Your Personal Style

As we’ve mentioned in previous posts, things like adopting a particular style (Bad Boy style, for instance) or popular trend just because you think it’s going to make you stylish or show personality isn’t the way to truly build your own personal style. It’s going to feel inauthentic and like you’re trying too hard. By starting with timeless essentials and building from there you’ll then be able to figure out what styles really speak to you as you gain more confidence and build on a solid foundation.

Ashley Weston

Men's Style Advice & More – from a Celebrity Menswear Stylist