Fashion Tips For Middle-Aged Men


Once men reach their 40's and 50's, they tend to become stagnant in their style. Being comfortable in your clothing is important, but it shouldn't take precedent as you age.

The good thing about getting a bit older is that you know what you like. You're not trying to "figure yourself out". You're not swayed easily, unnecessarily weaving your wardrobe with the latest trends. These qualities will serve you well as you're stepping up your style.

In middle-age, you're finished experimenting with your style, but you're not finished refining. What you should focus on now is timeless clothing that looks age-appropriate. Ditch the stuff you accumulated throughout your 20's and 30's that gets pushed to the back of your closet. Let's get that space working better for you, right now.

Keep Your Facial Hair Short

Facial hair ages us. There's a reason the kid who went through puberty early was the one who bought the beer.

A beard will make you look more distinguished but that might not be what you're going for.

Keep your face clean shaven, or with a bit of light stubble.

No Ankle Socks

Any socks that stick out above the shoe, but only cover the ankle should be tossed.

Go for no-show and crew socks in neutral colors. Once you have the basic colors, feel free to play around a bit and show some personality. Your socks are a nice way to have some subtle fun.

Save the white athletic socks for, well, athletics.

Ditch the Baseball Cap

Nothing will ruin a good outfit like the dad cap. It's the worn-in crown of most men over the age of 40.

In my opinion, men don't want to do their hair, or they are experiencing a bit of hair loss and want to disguise it. Wearing a baseball cap isn't the way to do this properly.

A guy who embraces his thinning hair is far more attractive than a guy who hides it under a frumpy looking hat.

Whatever your follicle production level is, take some time to style your hair and get a proper cut.

No Active Wear

This again comes back to a comfort thing. There is no reason to dress in athletic wear if you're not headed to the gym or exercising. Just because you are active doesn't mean you always need to wear activewear.

The biggest problem is with those basketball shorts. Swap them for something just as comfy, like some flat front cotton shorts that hit right at, or just above the knee.

Get a Pair of Cool Shades

This one is easy and will make a huge difference in your wardrobe. Tactical and sports sunglasses can tear up a perfect outfit.

Getting some new stylish shades are easy. Go for a classic wayfarer style. Ray-Ban popularized these. They look good on most face shapes and you can find a pair that's relatively inexpensive.

Cargo Pockets are for Cargo

If you're wearing cargo shorts and pants, you can do a lot better. I told a client recently that "cargo shorts are made for cargo, and no guy needs that much cargo." You need to re-think your priorities if you're carrying around that much stuff day to day my man.

Not only are cargo shorts a dated look, they bulk up your legs, making you appear larger than you are.

Swap them out for some form-fitting chinos and flat front shorts.

Step Up Your Shoes

Boat shoes, flip-flops, and running shoes seem to dominate the older man's closet. Your shoes are the foundation of your outfit and they deserve some attention beyond figuring out what is comfortable.

  • You need a pair of classic dress shoes that can work for many different occasions. If you have any square-toed dress shoes, they need to go. Get some patent leather, cap-toe, oxfords if you’re not sure where to begin.

  • For your comfy casual shoes, go with some classic trainers. These marry the comfort of athletic shoes with a timeless style.

  • Flip-flops should only be worn near water.

Stay away from younger styles

The worst thing you can do for yourself is try to look younger than you are. You’re a distinguished gentleman and age commands respect. Don’t spoil that. You don’t need trendy style to look good. Dressing age-appropriately also lets you steer clear of costly fads. Heres an easy list to get you started:

  • Too much jewelry. A watch is good enough.

  • Branded graphic tees.

  • Skinny jeans.

  • Showing too much skin.

  • Loud patterns and colors.

  • Overly-modern hairstyles.

The Bottom Line…

Most of the appearance problems older men face are related to fit, and dated style. If you still have pieces of clothing from your twenties, it’s time for an overhaul. Go for timeless items that will look good years from now. Clothing should make you look good for your age, not like you’re trying to work against your age.

If you need more help understanding how to look good and appropriate for you age, you should check out The Online Consultation - a one-on-one session where I personally work with you to give you detailed, actionable advice on how to look good. From hairstyle and skincare to suits and shoes, you’ll get the real answers you’ve been looking for. The sessions are capped each month, but check it out here to see if there are any openings. I’d be happy to help.