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.

Is Men’s Streetwear Attractive?

Streetwear can be a pretty divisive topic these days, it can look good but also can go really wrong.  While we always believe it’s important to cultivate a stylish essential wardrobe, it’s definitely good to also experiment with new trends and styles, especially as you’re on your journey to discovering your own personal style.

In this episode of 2 Minute Tuesday we’re weighing in on whether or not streetwear for men is attractive.

So, is streetwear attractive?  In our opinion, yes!  But it comes with a few caveats.

For The Right Person

Can streetwear look good? Yes, definitely.  But it has to work with your existing style and confidence.  If you’re the type of guy who can experiment with different styles and pull it off with confidence, then go for it.  It definitely takes a certain amount of swag to make it work.  If not, it can look fake and like you’re trying too hard.

Don’t Try Too Hard

Much like “Bad Boy Style”, streetwear is an overall look that can come off as really inauthentic if it doesn’t mesh well with your pre-existing overall look.  You can look like you’re wearing a costume and like you’re trying way too hard.  So, if you go for it, proceed with caution and give some consideration to when and where you’re adopting this vibe.

Should You Wear A Polo Shirt Under A Sweater?

It’s officially polo shirt weather but you’re probably still needing a layer here and there. In this week’s edition of 2 Minute Tuesday we’re going over a few rules when it comes to layering a sweater with a polo shirt. Here’s how to do it right.

Layering Tips

  1. Skip the polo under a sweater
    Wear a button up dress shirt or an oxford underneath a sweater, a polo shirt shouldn’t be worn over a sweater as the collar of the shirt doesn’t have enough structure. This goes for all types of sweaters – crewneck, v-neck, and shawl collar sweaters.
  2.  Wear a blazer, bomber, or Harrington instead
    If you do want to add a layer over a polo shirt, try a bomber jacket or Harrington jacket instead, they are better suited to the style of a polo shirt.  A blazer can be worn over a polo but we recommend sticking to a polo that has a neat, structured collar and stays put underneath your jacket.

 

 

Why “Bad Boy” Style Is Usually Cheesy

here’s a ton of content out there about dressing like a “bad boy” or an “alpha” and usually, it’s not a great look. Many men equate “bad boy style” with confidence and these things are simply not that intertwined as you think. Improving your style should be a pillar to growing your confidence, you shouldn’t adopt an exaggerated persona or image and expect confidence from a costume.

Why “Bad Boy” Style Is Usually Cheesy

It’s Not Really That Stylish
Sure, I love a good leather jacket and dark denim, they should be staple pieces in your essential wardrobe, but most of this so-called “bad boy” style involves a lot of things that don’t look great – over accessorizing with jewelry, out-of-style items, too much embellishment and “look at me” attitude. It’s a little too try-hard.

It’s Not Versatile/Practical
Ultimately it’s too one dimensional for most men. Having good overall style means having a well-rounded wardrobe with a mix of different items for a variety of situations. You can’t wear a t-shirt, boots, and jeans everywhere.

It’s Inauthentic
Typical “bad boy” items don’t work for everyone and every body type. Trying to fit your look and personal style into a particular box because it might make you seem cool or confident will only come off as fake.  Finding your own individual style and sense of self are way more important (and attractive!) than pretending to be something you’re not.

How To Dress To Impress A Woman

Many of you might be saying “I should dress for myself, not for women!” and while that’s true, putting thought and effort into how you dress and how you’ll be perceived by women (or anyone really!) is not only important, but it’s a fact of life.

Thanks to our friends at The Tie Bar for sponsoring this video, we’re longtime fans of their dress shirts and their ties, they’re sure to help you look amazing!

How To Dress To Impress A Woman

Keep It Simple – Don’t overdress for the occasion and try too hard (ie: wearing a suit when it’s the wrong occasion / too many logos/hyped trends). Simple looks from an Essential Wardrobe like dark denim and a blazer or bomber jacket or chinos and an oxford are great places to start.

Put In Effort – Even though you want to keep it simple, that doesn’t mean you shouldn’t put in thought and care to your look.

Fit Is Key – I repeat this all the time (because it’s important) but your clothes and look will be most attractive if they fit you properly and flatter your body type. Need some fit tips? Check out our Fit Guide, it’s all there!

Presentation – Make sure your clothes aren’t wrinkled or dirty. It may seem obvious but taking a few extra minutes to properly iron/steam your outfit goes a LONG way.

Dress For Confidence- Yes, I know this isn’t technically something you wear but in many ways, it’s just as important. Being confident and comfortable in your own skin is super attractive and will enhance your overall appeal and how you’re perceived. Feeling good about what you’re wearing goes a long way to helping you feel confident so it’s all intertwined.

Dorian’s Outfit

Dress Shirt

Bomber

Sneakers

Jeans

Shop everything from The Tie Bar right here:

The Tie Bar Shirts

The Tie Bar Ties

How To Dress For The Gym With Steve Cook

There’s definitely a right way and a wrong way to dress for the gym.  Sure, you’re there to get your sweat on but that doesn’t mean you should just wear a ratty old t-shirt and some sweats. Plus, you want to find functional items and fabrics that will wick moisture and provide performance benefits. For this video Ashley was joined by our friend and fitness guru, Steve Cook, to discuss how you should dress for the gym.

Performance Fabrics

Look for technical fabrics with performance benefits. There are many better options than an old cotton t-shirt and those heavy sweats can catch on things and restrict movement.

Watch Your Fit

Yes, there is such thing as too tight and nobody wants to see everything, so find a balance with your fit. Sleeveless is ok, but don’t be the guy in the tiny tank top showing excessive nipple. If you are going to be wearing base layers or tights, we recommend laying shorts and shirts over them.

Stick With Simple Colors

Keep it basic, stick to foundational colors like black, navy, grey, white. A pop of color or pattern is definitely welcome, so don’t be afraid to have some fun with your gym style.  You also don’t need to feel the need to match everything from head to toe, have some variance in what you’re wearing.

Logos

As we’ve discussed before, keep your logos minimal and try not to mix different brand logos, especially if they’re large and noticeable.

Have Gym Wardrobe

It can be tempting to just wear your old t-shirts and shorts to the gym. But just because you’re working out and getting sweaty doesn’t mean you shouldn’t cultivate a well-put-together look. That being said, no need to overthink it. Keep it simple, functional, and easy-to-wear.

Gym Style Picks

Tops:

Nike 1

Nike 2

Lululemon 1

Lululemon 2

GymShark 1

Gym Shark 2

Bottoms:

Nike 1

Nike

Lululemon

Gymshark

Don’t forget to check out our companion video over on Steve’s channel!

Extra special thanks to Steve for joining us, for more, check out his channel and site:

Youtube

Instagram

Website