How To Dress Your Best at Any Age
Dressing your age is a hot topic–no way around it. However, when it comes down to it, style is all about confidence. You want to look and feel good, no matter your age or what you’re wearing. Still, people change as they mature. Their accomplishments rack up and their identities evolve. Chances are, the person you were in your 20s won’t be the same person you are in your 30s, 40s or 50s and beyond. And as you change, so too should your wardrobe.
What does Dressing Your Age Mean?
So, what does dressing your age even mean?
For starters, it means dressing how you want others to perceive you. It also means having a wardrobe that makes you stand out (in a good way). Whether you want to exude success and authority, or effortlessly sophisticated and charming, your clothes say a lot about you.
If you’re a 45-year-old man at the height of your career, you probably won’t be wearing the same graphic T-shirt and jeans from college. At the same time, if you’re in your early 20s and just starting out, you probably don’t need a three-piece suit.
(Though, there are certainly exceptions to every rule.)
There might not be one “right” way to dress, but there are things you should consider as you mature. That way, as you get older and things change in your life, you’ll be prepared to meet them in style.
Does Dressing Your Age Matter?
In short, yes.
People often say that first impressions are everything, and they’re not wrong. There’s no reason to stop caring about your appearance just because you’re getting older. In fact, the whole point is to present yourself to others in the best light and convey confidence in who you are as a person.
How you choose to dress tells others whether they should be taking you seriously or not. Not only that but there are benefits to dressing for your age.
If, for example, you dress for success, you’re showing other people that you have self-respect, that you’re ready for anything, and that you have a strong character. The right wardrobe, along with a good skincare and grooming regimen, will inspire others to stop and listen to you when you speak.
Now, this doesn’t mean you should toss out all of your favorite clothes from your 20s the moment you turn 30 – in fact, you probably shouldn’t. Nor does it mean you should overdo it and try to look older than you are. You want to be noticed in a good way, so not dressing appropriately for your age could easily backfire.
Besides that, it’s not just mindset that shifts with age. Body proportions do as well. There are bound to be changes from decade to decade in the way you look. You might have a slim torso, youthful face, and broad shoulders through your 40s. But in your 50s and beyond, some of that muscle might have disappeared or you might have a slight belly. Conversely, you could get more in shape as you get older.
Either way, your attire should emphasize and flatter your body type and facial features. Don’t wear oversized or too tight clothes just because you have them or they used to fit well. Wearing clothes that complement your age and proportions will leave a much better impression on people while making you feel more confident about yourself. And if you feel confident, it will show.
How to Dress Your Age in Your 20s
Your 20s are the time for experimentation. It’s when you’re discovering who you are now and are starting to think about who you want to become in the future.
However, many people in their 20s don’t think about the big picture when shopping for clothes. More often than not, they purchase clothes as separate pieces and add them to their wardrobe without thinking about how they might pair them into a more cohesive style. Unfortunately, this typically results in a messy wardrobe filled with individual items they’ll never wear again, or that only look good with one or two other pieces.
Although it’s normal to try out different styles at this age, you should also think long-term. Start by adding several more versatile items to your closet that you can combine to dress up or down. That way, you’ll have multiple options readily available for any occasion.
Casualwear in your 20s
Be as bold as you like, but make sure you’re laying the groundwork for the next decade. This means adding a few staples to your wardrobe for easy mixing and matching.
At this age, you should have several pairs of well-fitted, dark jeans. These go with nearly anything and are relaxed enough for casual or social events. While you’re at it, get one or two pairs of bright-colored trousers to spice things up a little. Get a matching belt to wear with any pants that have belt loops, too. If you need more variety but don’t want multiple belts, choose a reversible one.
For the top, feel free to diversify. Whether that means graphic T-shirts or solid prints, you can wear whatever matches your personality. However, it’s a good idea to also have a couple of sport coats to wear with whatever base layer you’ve chosen. A classic navy blazer or mid-grey flannel is a great place to start. And then you can add in something with a subtle pattern once you get comfortable.
Sport coats are an extremely versatile piece of clothing. A well-fitted sport coat with dress shoes, a solid shirt, and khakis could work in semi-formal settings, for instance. Meanwhile, an unstructured blazer looks good with a graphic T-shirt and sneakers in casual settings.
You should have at least two or three pairs of shoes, including sneakers and dress shoes. If you want a little more color, wear some bright or patterned socks.
Finally, don’t forget to accessorize. The options here are nearly endless. Get a hoodie for chillier evenings or more relaxed outings. Add a leather bracelet or necklace for fun style points.
Just don’t overdo it or you might look sloppy. Try for one theme at a time until you find your best look. In other words, don’t pair a loud pattern with slacks and dress shoes.
Formalwear in your 20s
Most likely, you won’t need a lot of formal clothes in your 20s. Even so, it never hurts to have a few tailored pieces for interviews, the office, or other special events.
No matter your age, one of the most important things with formal attire is fit. A baggy or loose suit jacket will make you look like you’re trying too hard to seem mature, or that you don’t know what size to wear. You can get a few alterations done, but don’t go overboard. At this age, you might want to go for a tighter fit than what you’d wear later in life.
Choose a simple, two-button suit without any funky patterns or unnecessary details. For instance, this charcoal grey flannel suit pairs wonderfully with a light blue dress shirt and contrasting tie. If you already have a suit, consider getting a second suit in a different color to diversify.
Along with this, wear a white dress shirt (not button-down) for formal or business settings. Add a few collared dress shirts with subtle patterns and different colors to your wardrobe for variety. Don’t forget the necktie – you should have a couple in solid, dark colors.
Complete the look with a pair of leather Oxfords or black dress shoes and a belt that matches the pants. For an added touch, don a nice watch as well.
When in doubt, always err on the more formal side. A dark blue blazer and chinos might work in semi-formal settings, but they could make you look underdressed in the workplace.
How to Dress Your Age in Your 30s
For many people, your 30s are the time for some major life changes. This is when you’re starting to become more serious about your career, relationships, and so on. At this stage, you probably have many roles – husband, father, career man. So, you need multiple styles for different occasions.
The great thing about your 30s is that, with any luck, you’ve already laid the baseline for what you’re going to wear. You can still try out different things until you find what works, but you should have a pretty solid idea by the time you hit your mid-30s.
Start the decade by going through your existing wardrobe. Toss out anything that’s ill-fitting or that you haven’t worn in six months or longer.
Once you’ve done that, it’s time for an update. Go for quality over quantity and avoid extremes. This isn’t the time to reinvent your entire style, after all. It’s fine to follow some trends, but the more on-trend you try to be, the higher the risk you’ll commit a fashion faux pas.
Look for clothes that are higher quality and that come from quality brands. Whatever you buy should last a while, so it’s worth it to spend a little extra to make sure they’re durable. Try not to be swayed by a high price tag. Even if it costs more now, it will save you money in the long run if it lasts a long time.
Casualwear in your 30s
Cultivate and expand on what you already have in your closet. This means shoes, outerwear, shirts, jeans, and accessories. Even for casual wear, your clothes should be at least semi-tailored to be flattering. However, you should avoid going ultra-slim, even if you have a trim figure.
Unlike in your 20s, this is a good time to start adopting a more smart-casual look. You can still wear denim jeans, but you should also start swapping them out with chinos and khakis. For the top layer, wear a solid T-shirt or an Oxford shirt – the Ice Blue Oxford Cloth Dress Shirt looks especially stylish with a checked sports jacket or v-neck sweater.
Alternatively, go for an unstructured blazer with a slightly shorter cut and high-quality fabric. For slightly more formal events, such as weddings, get a tailored overcoat that’s structured without being stuffy. If the overcoat is short enough, you could also pair it with jeans for a more casual aesthetic. Don’t be afraid to add some color, but do avoid loud patterns. Another option is to wear a sports coat with navy jeans, a solid T-shirt, and quality leather shoes.
Formalwear in your 30s
While you should still avoid padded suit jackets, it’s time to update your formal wear. A structured overcoat will work in cold weather or for certain formal occasions, while a classic navy blue blazer looks good in any formal setting.
Add a few custom dress shirts to your wardrobe. You can still go with bolder colors or subtle patterns without looking immature. Just make sure the dress shirts fit well without being super tight at the collar or tapered at the waist. For the shoes, you can’t go wrong with Black Whole Cut Oxfords. They’re sleek, elegant, and perfect for any formal setting.
Make sure you also have a semi-casual suit for slightly less formal events, such as a day at the office or dining out. Navy blue and dark gray are good options here as well as brown if you’re a bit more sartorially adventurous. Keep things minimalistic, but feel free to accessorize with a dress watch with a class leather or metal band.
How to Dress Your Age in Your 40s
First off, your 40s aren’t the decade for trends. At this point, you know what makes you look and feel good. So, while you can still keep up with modern fashion, you shouldn’t make any sudden changes just because something new and popular has arrived on the scene.
In all likelihood, the previous decade brought with it a lot of personal and professional accomplishments. So, now you can celebrate your success while finding comfort in your style.
Focus on elegance and sophistication. You can still use much of the wardrobe you built up in your 30s, but a few changes are in order. Start by narrowing down your color palette, based on what you already own. Pay attention to the subtle details like patterns, textures, and fabrics.
Just as you don’t want to make any extreme changes, you also don’t want to grow apathetic about your style choices. Upgrade your wardrobe and add more accessories. This could be a few more neckties, a statement piece like a sophisticated gold watch, pocket squares, or a pair of gentleman’s gloves.
If some of your older clothes don’t quite fit, see if you can get them tailored to suit your current proportions. Sometimes a simple change like this is all that’s needed for a new lease on life – and your style.
Casualwear in your 40s
Both your casual and formal wear should be based on a good foundation of neutral colors like khaki, brown, white, grey, and black. Other good color options include navy blue, forest green, and burgundy. Use brighter colors sparingly or as an accent.
Even your casual clothes can be stylish. Combine a collared dress shirt with slacks or navy blue cotton pants. For a more rakish look, layer it with this Medium Brown Loro Piana Plaid Sport Coat. Appear even more refined (without being too formal) by adding a pocket square and penny loafers.
Other options for the pants include dark-colored jeans and khakis. If desired, go for pants with a slightly shorter length that reveals your ankles from time to time. Add a dark polo shirt and snappy shoes like brogues for a more sophisticated look.
Formalwear in your 40s
Although your casual wear should also be tailored to your proportions, this is doubly important for formal attire. Toss out anything that’s overly form-fitting and opt for a tailored suit that conveys authority and causes people to do a double-take instead.
For example, this Navy Blue Flannel Chalk Stripe Suit speaks of confidence, power, and maturity. It looks great with or without a vest and has the added bonus of making people pay attention when you enter the room. Pair it with a plain white dress shirt, necktie, belt, and brown leather shoes. Make sure the cuffs of your shirt are slightly visible. If desired, finish off the look with a luxury watch, pocket square, and leather briefcase.
If you want a slightly less formal look, opt for a navy blue, black, or grey blazer. Either way, it’s hard to go wrong with a dark, tailored suit made from high-end fabrics like wool or flannel.
How to Dress Your Age in Your 50s
At this stage in life, you’re confident in who you’ve become and have accomplished a good deal of things. Even so, there’s still more to do and your style should reflect this.
You should already have most of the fundamentals in place, so now’s a good time to refine your style even more. First and foremost, your clothes should be precisely tailored to fit your form. If you don’t already have one, consider getting a personal stylist or tailor.
In your 50s, don’t be afraid to show off how sophisticated you are. You should still be comfortable in your clothes, but you should also avoid overly casual items like sweats or T-shirts. That said, you should look dignified, not stodgy.
As with previous decades, your wardrobe could probably use some updating. When shopping for new pieces, go for luxury and elegance. Style constantly evolves, but you should still focus on the quality and construction of any new clothes.
Add a few select pieces to existing outfits to give them some flair or finishing touches. If you have too many clothes, donate or discard never-worn clothes to simplify your wardrobe.
Casualwear in your 50s
At this age, you don’t have to wear suits for a specific reason anymore. Even so, you’ll want to choose a suit that fits the setting and the mood. Striped, plaid, and solid are all appropriate options.
Alternatively, mix and match sport coats with high-quality slacks. Pair them with a turtleneck or open-collared dress shirt for a more sophisticated, but relaxed look. While you’re at it, add a few accessories like cufflinks or a stylish hat. Whatever your style is, let your personality shine.
Since you are going for a more casual aesthetic, consider getting a tweed vest or jacket to go with a pair of linen trousers. If you’re worried about looking too reserved or somber, you can even add the occasional necktie in a fun pattern.
Even if you’re not in a business setting, it’s still a good idea to have several suits on hand just in case. Choose suits in solid colors or with subtle patterns. For even more casual days, opt for sharp dress shoes, a sweater or cardigan, and relaxed slacks. As always, avoid anything too baggy – instead, go for semi-fitted.
Formalwear in your 50s
Thanks to the previous decade, you should have several appropriate business suits in your wardrobe. If needed, add a couple of waistcoats, and double-breasted jackets as well. Remember, high-quality fabrics like thick wool are your friend, but not everything has to be designer.
Meanwhile, update your statement pieces and accessories with a new Rolex watch, luxury overcoat, or pocket square. If you find options limited, diversify with a few new neckties or cufflinks. Textures and patterns make a huge difference in your style, so try out a couple of new things.
How to Dress Your Age 60+
Your 60s should be a direct continuation of your 50s. Regardless of the setting, your clothes should speak of luxury, refinement, and sophistication–because with age comes widsom, right? The bulk of your wardrobe should be completely tailored to you.
If you find yourself with too many clothes in the closet, it might be time to donate the excess. At this age, having fewer options might even be a relief. It’s still okay to have a few more casual pieces, though.
However, there’s no need to sacrifice either comfort or style. Your attire should be timeless and represent you in the best possible way. Use the previous decade as the foundation, but embrace any new changes to your hair, face, and body.
Casualwear in your 60s
In your 60s, you can still be stylish without taking yourself too seriously all the time. Don’t be afraid to switch to less structured attire for casual occasions. Choose wrinkle-free dress shirts and pants that are comfortable but look good. If needed, go for an elastic waistband (but never wear baggy clothes).
Just like before, chinos and cotton khakis are tried-and-true options. If you want more texture and a dressed-down style, go with corduroy pants instead of chinos.
Along with this, choose a flannel, button-down shirt for a relaxed, but dignified look. You can still have a few T-shirts and polo shirts, as long as they’re tailored to your proportions. If you don’t already have them, get a pair of non-slip shoes, too.
Formalwear in your 60s
Even if you’re retired, there are still plenty of opportunities to dress up. For social events, pair a navy blazer and cotton khaki pants with a dress shirt in a complimentary color. For more formal settings, wear a tailored three-piece suit. Accessorize with Oxfords and a gold watch for a timeless, classic look. Add layers if desired, but avoid a bulky look.
How you choose to present yourself to the world has a major impact on how others view you. Dress the way you want to be seen. Ask yourself, do you want to stand out or blend in? Do you want to convey power and sophistication, or do you want to seem more relaxed and approachable?
Whatever the case, your overall style – from hair to wardrobe – will leave an impression on others. You can refine your style as you mature, but it helps to set the foundation early on. Reevaluate your wardrobe every so often to make sure your clothes still represent who you are and how far you’ve come in life.
When in doubt, get a second opinion from a personal stylist or tailor. And remember, style is all about confidence and perception. There’s no one set rule about what you should wear, but you should take pride in your appearance and your accomplishments.
Thanks for reading.
He Spoke Style