How to Dress Your Age – Tips, Tricks and Style


How to Dress Your Age – Tips, Tricks, and Style

Knowing what to wear and how to pair up those clothes can become tricky as you get older. Don’t get me wrong, there are no cut out, laid down rules for how to dress your age but fashion trends for older men are quite different from that of younger men. You will do well to get that point right.

Kenneth Cole REACTION Varsity Bomber Trucker Jacket

How on Earth should Young Men Dress

That title might not look as promising as it seems but don’t get me wrong. Am not trying to straighten you out or lecture you on what you are doing wrong, am not your Dad. But as a young man, you have all the liberty in the world to push the boundaries of fashion. Here are some tips to help you get the most out of your experimental days:

How to Dress in your 20’s

Dressing in your 20’s isn’t as complicated or sophisticated as the rest of your older years. At this stage, you have the liberty to experiment with lots of colors and styles. You are saddled with lesser responsibilities, more time to run out with friends but limited by cash. Staple pieces of clothing even if they are attractive might not be within your reach because of the price tag associated with most of them.

So you opt for cheaper and trendier outfits. However, this is the best time you start working out what style and outfits you prefer. Jump between outfits, from the hip star one week to a more relaxed style next week. Don’t be afraid to work out your own style even when friends raise an eyebrow over it.

Here are some Useful Tips on How to Dress in your 20’s

  • Experiment with things

Your 20’s are the best time in your life to try out more bold and darling looks, before settling down to more classic styles. Early to mid-20’s are the most catered for groups by big brands when it comes to clothes. Bright colors and prints will suit nicely with their dress aesthetics. For now enjoy the oddities of fashion later on you will look back and laugh at the way you once dressed.

  • Get yourself a very Good barber

A decent haircut will definitely improve the way you look in any outfit. While I advise that you keep things simple you can still try some really crazy cuts once in a blue moon. You need those crazy moments in your life to refer back to. Mohawk hairstyles seem to be in trend these days. Try out buns and pompadours for a more decent looking haircut.

Some hairstyles can be quite difficult to maintain, so have that in mind when you pick a style. You want something that can be maintained on its own without the fuss of annoying hair products.

  • Get a Good Watch

Casual looking watches will be more important for you than formal leather watches. Since most of your outfits will lean towards the more casual side of life. Accessories are very important to dress combo these days so get a staple watch to match those outfits. Spend a little more to get some good watches that will match most of your outfit combinations.

  • Collect a couple of white T-Shirts

Prepare to spend some extra bucks on white shirts. They are a great dress companion and the best thing to happen to black, blue and monochrome dress combo. They can help you create a great casual look or help you dress up your outfit. Change up the style, opt for textured whites as the weather demands and play around with sleeves.

 How to dress like a 20 year old

Top Picks (White Sneakers)

Lacoste Adidas Puma Converse


Top Picks

Adidas Adidas Overcoat Wantdo

How to Dress up in your 30’s

As you age more into your thirties, you might still be pardoned and get away with the trends of modern day society but at this stage, you should start thinking of more classic styles to replace the childish street wears of your 20’s. Your 30’s are the best time in your life to dress up properly, this is the best time to rock smart-casual wears, yea you held me right, those blazers and jeans combination they blend in seamlessly with this age group. You are naturally gifted with a blend of youth and some maturity.

Keep your body shape in mind opting for more streamlined fitted clothes to suit your body shape. Also get formal with your haircuts if you want the workforce to take you seriously.

Your wardrobe should include fitted patterned suits and some marching tie accessory. Go bold with your casual look with more patterned shirts than with bold colored shirts.

How to Dress Like a 30 Year Old Man

  • Suits and Blazers should form the Buck of your Wardrobe Clothes

At this stage of your life, the more suits you get the better. You might have gotten away with just one suit in your 20’s but now people will be less forgiving. You need them in different colors, styles, and patterns.  There are many ways to wear a suit so you don’t have to be worried about waiting for only a formal occasion to rock one.

  • Try investing in Go-to Items

Go to clothing will save you lots of time. You aren’t blessed with the free time you used to have in your 20’s, work and probably family gets the buck of your attention now. You need go-to clothing that will save you time. A few fitted blazers oxford shirts and wingtips are clean examples of go-to clothing. Add some perfectly cut slim or skinny jeans to that list.

  • Opt for Labels

You no longer have the liberty of going with the trend jumping on anything that is hot at the moment. At this stage what you should do is define your style and stick with a few trusted labels. Stay clear of cheap trend focus clothes but rather go for fewer, more expensive but quality products. Here when it comes to quality, less is more. People of your age bracket will notice it and compliment you for it.

How to dress like a 30 year old

Top Blazers

Ck Fitted Polo Assn.

How to Dress in your 40’s – Middle-Aged Fashion

At this stage in your life, you are least bothered with trends and fashion; you should rather look to develop your own style. Weed off those exuberant clothing from your 20’s and 30’s and focus on what works for you.

Fitting is more important for a 40-year-old than colors and patterns. A simple white tee and a nice pair of jeans can work wonders till you are 50 as long as they fit properly and are of high quality. Invest wisely.

Follow these tips on how to dress like a 40 Year Old Man

  • Define your haircut and stick with it

Haircuts as discussed early can radically change a man’s appearance. In your 40’s you might begin to see a thinning out and receding hairline tag. A shorter and smart haircut could help to mask those inevitable male pattern baldness.

  • Fitting is key

Slim fitted pants and suit might have worked well in your younger days but my bet is that you won’t look as trim as you used to. Avoid slim fits and opt for more regular fitting clothes. As for jeans, say way from skinny jeans. Opt for regular fit jeans instead.

  • Overhaul your Wardrobe

As you approach 40 there is sure going to be clothes from your 20’s and 30’s still laying around. Some might still work well but others might have just overstayed their usefulness. Please get rid of those you have outgrown and stick to more flattering pieces.

  • Choose lighter Colors over brighter ones

Navy and grey can work well for men approaching their 40’s than do brighter colors form your 20’s and 30’s. Black can still work here if worn rightly.

How to dress like a 40 year old

Top Picks (White Tee)

IZOD Ralph Lauren 28 Palms

 How to Dress in your 50’s

Fashion in your 50’s is no different from that of your 40’s. The usual focus on fitting rather than colors still applies here. You are still going to look great on a nice fitted suit but casual outfit might start getting trickier to pull off.  At this stage ease of on the numerous uses of trainers and sneakers favoring loafers and easy wear shoes.

Useful Tips on how to Dress like a 50-Year-Old Man

  • Accessorize to level things up( Spend that money)

Look around you. Which age group do you see use accessories a lot? Your guess is as good as mine, older more matured men. The homburg hats, bold ties, quality watches etc. Accessories can help put finishing touches to an outfit whether it’s a simple shirt and jeans or a sophisticated three-piece suit.

Think leather strap watches and nice framed sunglasses. Your refinement as an older gentleman should come with higher quality accessories.  For crying out loud, get a Rolex dude!

  • Lastly, Keep your Hair in Check

Do not fall into the circle of allowing your hair and bread go unchecked? Use good hair care products to keep your hairlines and beard in check.

How to dress like a 50 year old

How to dress like a 50 year old

How to Dress Your Age in Summary

  1. In your 20’s, you’re the king of hip-hop and street style. You got game going and are at liberty to experiment with in trend fashion. However, that freedom is limited by cash.
  2. In your 30’s streamline your wardrobe and add more luxurious items.
  3. In your 40’s look to overhaul your wardrobe eliminating those clothes from your 20’s and 30’s and stick to those that flatterer your style.
  4. At 50 and above, accessorize like no other. Get quality watches and nice looking accessories to match most of your rather formal attires.

On That Note

Hopefully, the advice in this article is enough to stir you in the right direction. Dressing your age doesn’t have to be a daunting task. They are basically no laid down rules to follow just little bits of advice here and there. As you get older try to tone things down a little opting for regular haircuts and simple colors.


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