How To Dress Your Age – Tips For Your 20’s, 30’s, 40’s, 50’s and above

Dress Your Age - Tips For Your 20's, 30's, 40's, 50's
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So many women struggle to learn how to dress their age. It’s hard because that number is constantly changing, but it’s hard to know how to adapt your style to it. And I think we all (perhaps subconsciously) don’t want to give up those glory years. So today let’s talk about how to dress your age.

This is not a one-size-fits-all solution and there are variables for each age. But I want to share with you some tips to help you keep your style elegant and age-appropriate no matter what your age.

The best place to start is to figure out your style. Here I have a FREE Wearable Wardrobe Guide that you can sign up for that will walk you through cleaning out your closet, finding your style, getting better at shopping, and more.

How to Dress Your Age | Tips for your 20's, 30's, 40's and beyond!


1. This is the age of experimentation.

The fun thing about your 20s is that you get to play around with a lot of different styles and see which one works for you. Experiment with fashion and don’t be afraid to try new trends. You’ll look cute even if the trends are terrible. We’ve all been there. Sneakers, mini dresses, graphic tees, t-shirts, crazy jeans…you can wear it all and get away with it. Take your body type and lifestyle into account (don’t wear your crazy jeans to a casual office job), but have fun with your wardrobe. Don’t get stuffy too quickly.

2. Invest in a few pieces you’ll need this season

This is the time of your life when you will have a job interview, attend weddings, have babies, and many other big life events. Invest in a few quality pieces like classic black or nude heels that you can wear to weddings and interviews, a tailored jacket that you can wear with trousers, a skirt or a dress to an interview, and a nice wool or suede coat. /leather jacket to wear during the colder months.


1. It’s time to start figuring out your style.

Let’s start by cleaning out your closet. Need help with that? I have the full post HERE. There’s still time for a bit of experimentation, but these are the years when you should start figuring out your style, and that starts with going through your wardrobe and ditching the pieces that don’t belong.

Dressing Your Age: Fashion Tips to Follow from 20s to 50s

2. Quality over quantity.

In your 30s, you should start investing in your wardrobe. Does that mean you have to spend $100 on every piece in your wardrobe? Or that you can no longer shop at Target? Of course not. Investment pieces go on sale and Target sometimes has quality stuff too. But as my mom always says, “cheap people pay twice” and it’s so true. It’s time to stop buying things just because they’re cheap. I think we’d all rather have 10 shirts in our closet that last for years and make us feel amazing than 30 shirts that all get ruined after one wash, dusty and shapeless after a few wears.

3. Let’s add some sophistication,

Your 30s is the age when you should start adding a bit of sophistication to your look, balancing youthful pieces with chic and classic pieces.

Here are some examples: if you’re wearing a graphic tee, add a blazer over the top or pair it with pointed flats to give the outfit a smart, classic touch. If you’re wearing sneakers, pair them with jeans and a blouse rather than a t-shirt. I could give a million more examples, but I hope you get the idea.

“Mating juveniles with juveniles equals juveniles. The pairing of youthful and classic is age-appropriate.”

How To Dress For Your Age (20s, 30s, 40s, 50s+) | Men's Guide


1. It’s not time for granny clothes yet!

This is the peak of your life! Don’t feel like you’re over the hill and it’s just granny clothes from here. You can still be super chic and youthful and you can add those fun pieces. This is the age when you’ve probably figured out what you do and don’t like and realize that you don’t care what other people think. Boost your confidence and have fun with your style!

2. Classics are key

Classic pieces will be your best friend as they give an age-appropriate feel while wearing youthful pieces. Start adding button-down shirts, shirt dresses, blazers, smart flats or loafers, or classic white sneakers to your wardrobe.

It’s time to ditch the distressed cuts and short hems. Just above the knee hems should be the shortest. If your legs are killer and you want to show them off, aim for pencil skirts, bodycon dresses, and skinny jeans/trousers that are fitted but leave a bit to the imagination rather than giving it all away.

Stay away from oversized. As you go through menopause, your weight may fluctuate and you may be tempted to go for oversized pieces to mask any size change. But choosing clothes that fit will make you look slimmer and accentuate the best parts of your figure. If you want to try something super trendy, try a trendy shoe or bag.

How To Dress In Your 30s - 15 Styling Ideas

3. Your tailor will soon become your best friend

Spend a few extra bucks and have your clothes tailored. Tailors are quite cheap and make a huge difference. Your pants and jeans should be the right length for your height, not gaping at the waist, and your shirts and jackets should have seams and details that give you shape. Let the clothes work for YOU!


1. Avoid the “granny” style.

As you get older, pastels and small floral prints can easily feel “grandma”, so buy bright colors and bold florals. You can also never go wrong with a sleek black and white combo or classic navy. Now is not the time to play it safe – go ahead!

2. If you haven’t figured out how it fits yet, there’s no time to waste!

If you’re over 60 and your clothes don’t fit you, it’s time to go to a tailor and get them fixed. A tailor can help you choose the right length of pants, the right cut for your waist, or the best sleeve length for your arm. And remember, these pre-tailored pieces like blazers and pants can always be adjusted for an even better fit.

Everyone’s body is different as they age, so don’t rely on one size fits all.

“Don’t get frustrated, get it tailored!”

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