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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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How to Dress Your Age

white skirt and blouse

similar white top, similar white skirt, similar sandals, similar hat

 

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.

 

READ THIS FIRST!

As you go through these tips, these are just suggestions! There’s no fashion police — where what works best for YOU and YOUR STYLE and YOUR LIFESTYLE!

The best place to start is to figure out your style. I have a FREE Wearable Wardrobe Guide RIGHT HERE that you can sign up for and it’ll walk you through how to clean out your closet, find your style, get better at shopping and more.

 

 

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.

I spent my twenties trying to look way older, wearing lots of heels and blazers and professional outfits, and although I still had fun my with my closet, I feel like I was trying too hard and not enjoying or experimenting with my casual style enough.

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 interviews, attend lots of 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.

Also, your budget is most likely going to be small during these years, so try thrifting or shopping at less expensive stores like H&M and Old Navy or Target where you can find fun pieces without spending a fortune.

Save your pennies and splurge on just the classics that you’ll wear over and over and are super versatile. But you don’t need a ton at this stage!

 

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 plenty of time for experimenting with your style and letting it evolve, 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.

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. You can still do shorter ones, but if your cheeks are hanging out of your shorts, it’s time to toss them.
  • 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 or clingy.

If it’s not a “HECK YES,” then it’s a “NO.” Just repeat that to yourself every time you shop.

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. I’ve heard these are the best years yet, so let’s dress like it!

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 and definitely can add those fun pieces in. This is the age when you’ve probably figured out what you do and don’t like, and what does and doesn’t work for your body, and you realize that you just don’t care what other people think. Rock that confidence and have fun with your style!

2. Classic is key

Classic pieces are going to be your best friend, because they add that age appropriate feel while wearing youthful pieces. Start adding button down shirts, shirt dresses, blazers, chic flats or loafers or classic white sneakers to your closet. These can all be paired with more trendy pieces too! I love seeing women in this age category rocking their trendy Golden Goose sneakers with a chic button up and an amazing pair of jeans. Or a matching athleisure set with a pair of classic white sneakers and a classic denim jacket.

It’s time to phase out of distressed pieces and super short hemlines. 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 approach menopause years, your weight can fluctuate, and you may be tempted to choose oversized pieces to mask any size change. But choosing clothes that fit, as well as pieces that have structure instead of clingy, thin fabric, will actually 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.

 

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 is not the time to play it safe – go bold!

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 probably 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.

 

Remember, YOU get to decide what to wear!

Don’t forget – these aren’t hard and fast rules, only suggestions! No one is stopping you from wearing what YOU want, but I hope these tips are helpful as you figure out what to wear as you age.

 

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54 Comments

  1. Gaby says:

    I’m 42. I once clicked on an article similar to this one – how to dress in your 40’s. This is what it said, pardon my french, “where whatever the f you want!” 🙂

    • Merrick says:

      Haha that’s fantastic advice. I feel like some style guides say you need to get stuffy in your 40s — not so fast! I hope you followed their advice 😉

  2. Lindsay says:

    @ GABY BAHAHAHAHAHA! YES!!!!!!!!!!!!! I AM 40 AND I WEAR WHAT I WANT! I WEAR DISTRESSED JEANS, SHORTS AND DENIM SKIRTS, I WEAR CROPPED TOPS (WITH HIGH WAISTED PANTS OR SKIRTS). I DON’T WEAR MINI SKIRTS THOUGH…I DON’T REALLY LOVE THAT STYLE ON ANYONE! Same with tube tops lol! I AM FIT/ATHLETIC AND TALL though so Maybe not all ladies in their 40’s would feel comfortable wearing what I wear. I’m at the office today in a RACER BACK tank dress (maxi) and pointed toe loafers. Yesterday I wore a unfinished hem denim midi skirt and button up collared blouse that tied at the waist with flat nude oxfords. I am not really into the whole slacks and blazer outfit for work lol!

    • Merrick says:

      You sound like you have the most amazing style! I hope I dress just like you when I’m 40. I think the key for your style is that you have those classic pieces (like your oxfords and loafers) integrated into the youthful pieces — I love that. We need you as the poster child!

  3. Sarah says:

    Ouch, girl. Not the best move to lump 40’s and 50’s together. I’m 43 and love to have fun with fashion. Dressing for your/because of your age is so out of style.

    • Ainsley says:

      Thank you! Im a week away from turning 40 and couldN’t afree with you more.

      I found the adVice here very stuffy and generic.

    • Idie says:

      I am approaching 50, which is a hard pill to swallow because I don’t feel a day over 35. You ladies will know the feeling one day. 50 is the new 40. I see them as the same!

  4. T says:

    Do you have any suggestions for longerish shorts for Petite women in their 50s? It’s hot where I live, and sometimes a dress isn’t practical.

  5. Pip says:

    There is only one thing a person needs to look wonderful – confidence. Fashion is not determined by age(or weight, or gender, or…)!!! If your wardrobe has you feeling beautiful and you radiate that confidence, people react to you, not the items of clothing that you might be wearing. Let’s stop pigeon-holing people by categories. It is time we celebrate and embrace individuality!

  6. Stephanie says:

    I love this post – so helpful. I’m looking forward to the next post on this topic!

  7. Townes says:

    Ummm or we can just let People wear what they want despite their age

    • candace says:

      “REMEMBER, YOU GET TO DECIDE WHAT TO WEAR!
      Don’t forget – these aren’t hard and fast rules, only suggestions! No one is stopping you from wearing what YOU want, but I hope these tips are helpful as you figure out what to wear as you age.”

  8. Kristy Haight says:

    Merrick! Love this post! And i may have just had a minir heart aTtack realizing im in the 40-50’s age group! Hahaha

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  11. Maureen says:

    Im 66 and can still wear a shorter skirt say 2 inches above the knee. A lot has to do with body shape and genetics. I can wEar distressed jeans and boots as well. I dont look 66 so why dress like it. I find certain brands fit better than others rather than using a tailor. Working ouT, eating right and staying fit is KeY to aging gracefully. Thanks for your ideas.

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  21. Great Guide! It’s very worthful. Nowadays this is the major QUESTION that confuses a lot of people what to wear according to their age that looks classy as well as sober. As owning a handicraft company we also go through a lot of stuff like this what should we make naturally that looks good on all or a specific age group of people. I THINK THAT BY READING THIS THEY WOULD GET A LOT OF IDEAS REGARDING CLOTHES. Keep posting!!!

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