How To Dress Your Age | Tips For Your 20's, 30's, 40's And Beyond!

One of the biggest challenges I see women make is learning how to dress your age. It’s a tricky thing and has a lot of variables, but let’s tackle it together and learn a few basic tips.

I want you to learn how to dress your age

So many women struggle with learning how to dress their age. It’s tough, because that number is always changing, but it’s hard know how to adjust your style accordingly. And I think we all (maybe subconsciously) don’t want to let go of those glory years. So let’s talk today about how to dress your age.

This isn’t a one-size-fits-all solution, and there are variables for every single age. But I want to share with you a few tips that will help you keep your style classy and age appropriate no matter your age.

Dressing your age in your 20s

1. This is the age to experiment.

The fun thing about your 20s is that you can play around with a lot of different styles and see which ones feel right for you. Get experimental 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-shirt dresses, crazy distressed jeans…you can wear it all and get away with it. Obviously take your body type and lifestyle into consideration (don’t wear your crazy distressed jeans to your business casual office job), but have FUN with your closet. Don’t get stuffy too fast.

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

This is the time of your life when you’ll have job interview, be attending weddings, baby showers, and lots of other big life events. Invest in a few quality pieces, like some classic heels in black or nude that you can wear to weddings and interviews, a tailored blazer you can wear with pants or a skirt or a dress to an interview, and a really nice wool coat or suede/leather jacket you can wear during the cooler months.

Dressing your age in your 30s

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

Let’s start by cleaning out your closet. Need some help with that? I have a whole post HERE. There’s still time for a bit of experimenting, but these are the years when you should start figuring out your style, and it starts by going through your closet and tossing the pieces that don’t belong there so you can start to dress your age.

What should you toss?

• ANYTHING from high school. Just don’t.
• Super distressed jeans — a few holes are fine. The shredded ones must go.
• Booty shorts. Time to add a little sophisticated length.
• Anything that doesn’t fit or that’s worn out. I talk a lot about that here.
• Check out the rest of my closet cleanout tips here.

2. Quality over quantity.

Your 30s are when 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’t shop at Target anymore? Of course not. Investment pieces go on sale, and Target has good quality stuff sometimes too. But as my mom always says, “cheap people pay twice,” and it’s so true. It’s time to stop buying things just cause they’re cheap. I think we’d all rather have 10 shirts in our closet that will last for years and make us feel amazing, than 30 shirts that all get ruined after one wash, pill after a few wears, and are shapeless.

3. Let’s add some sophistication, baby

Your 30s are the age when you should start to add a bit more sophistication to your look and balance out the 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 add a chic, classic feel to the outfit. If you’re wearing sneakers, pair them with a pair of jeans and a blouse rather than a tee. There are a million more examples I could give, but I hope you get the idea.

“Pairing youthful with youthful equals juvenile. Pairing youthful with classic equals age appropriate.”

Dressing your age in your 40s and 50s

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

This is the prime of your life! Don’t feel like you’re over the hill and it’s only grandma clothes from here on out. You can still be super chic and youthful, but it has to be age appropriate.

2. Classic is key

Classic pieces are going to be your best friend. Start adding button down shirts, shirt dresses, blazers, chic flats or loafers or classic white sneakers to your closet.

It’s time to phase out of distressed pieces and short hemlines. Just above the knee hemlines should be the shortest you go. If your legs are killer and you want to show them off, focus on pencil skirts, bodycon dresses, and skinny jeans/pants 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 can fluctuate, and you may be tempted to choose oversized pieces to mask any size change. But choosing clothes that fit will actually make you look slimmer and accentuate the best parts of your figure.

If you want to try something trendy, try a trendy shoe or bag. Stick to the classic pieces for your clothing.

3. Your tailor is about to become your best friend

Spend a few extra bucks and get your clothes tailored. Tailors are actually pretty inexpensive and they make a huge difference. Your pants and jeans should be the right length for your height, there shouldn’t be gaping at your waistline, and your shirts and jackets should have seams and details that give you shape. Let the clothes work for YOU!

Dressing your age in your 60s+

1. Steer away from “grandma” style

As you get older, pastels and small floral prints can easily feel “grandma,” so buy the bright colors and the bold florals. Also you can’t ever go wrong with a chic black and white combination, or classic navy. Now’s not the time to play it safe.

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

If you’re in your 60s and your clothes aren’t fitting right, it’s time to march yourself to the tailor and get that fixed. The tailor can help you decide the right length for your pants, the right fit for your waist, or the best sleeve length for your arm. And remember, those pre-tailored pieces, like blazers and pants, can always be altered as well to fit you even better.

Everyone’s body is different as you get older, so don’t rely on standard sizing to work every time.

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

3. Avoid anything “costume-y”

Sequins, fringe, broaches, feathers…anything that could read “costume-y” is a no-go. Stick with those classic pieces. You can still try trends, like colors, prints, styles of shoe, etc, but steer clear of jumping on any super trendy wagons.

white top, white skirt, similar sandals, similar hat

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