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You Asked: How Can I Tell My Mother to Dress Her Age?

Dear Sugar,

I have run into quite the dilemma as my mother has gotten older — she just turned 50, but she's dressing like a 15-year-old! My two younger sisters (13 and 16) are still living at home, so I guess they are the only ones she has to look to for fashion advice. On her 50th birthday, she wore a skintight sweater with black leggings to a party we threw for her. This wouldn't be so bad, but the tights she wore belonged to my 13-year-old sister, and for lack of a nice way to put it, my mom doesn't quite have the physique she used to. As guests started to arrive, it was obvious that they were shocked by her outfit choice.

She has a wonderful boyfriend who she has been seeing for about a year now, so she isn't trying to "dress to impress." He's a pretty laid-back guy who has said on several occasions that he prefers her in jeans and a hoodie rather than all "gussied up." I don't know if it's turning 50 that's spurring a midlife fashion crisis or if it's the fact that my two older sisters and I no longer live at home to give her advice on what to wear, but my mom's clothes are starting to get a little out of control. She always used to look great and put together, so how can I tell her that she isn't quite dressing appropriately for her age without hurting her feelings? — Embarrassed Elsa

To see DearSugar's answer

Dear Embarrassed Elsa,

As with most moms, I'm certain that your opinion means a lot, so you're going to have to tread lightly in order to avoid hurting her feelings. Since she used to dress more to your liking, you might be right — she could be having a midlife fashion crisis. Whatever the case, I think your mom's boyfriend has the right approach. Instead of harping on her for the things you don't like, compliment her on the things you do. Tell her how great she looks when she wears something you like and if she asks for your advice, be sure to give her an honest answer in a loving way. If you attack her wardrobe choices, she's bound to feel bad about herself and, in turn, she might try to dress to impress even more.

Mother's Day is just around the corner, so perhaps you and your sisters could take her shopping or pitch in to buy her a few new pieces that you'd all like to see her in. Since they'll be a gift from the ones she loves most, hopefully she'll wear them, especially when she's around you girls. In addition to guiding her in the right direction, you should talk to your younger siblings and urge them not to let your mom borrow their clothes anymore. The key thing to remember is that dressing your age doesn't mean you can't still look hip and stylish, so hopefully with some positive encouragement, your mom will be able to realize that too.

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onesong onesong 7 years
lol. i would smack my mom. she knows to ask me now if she's unsure (which she isn't often) and she values my honesty. just tell your mom that you're sorry to be blunt but your 13 year old sister's clothes aren't appropriate for her and she needs to buy some stuff that fits her. hopefully that will shock her out of it. good grief!
ckeller825 ckeller825 7 years
Sometimes my mom is the same way (dressing in leggings with some funky-pattern oversized sweater, or wearing jeans that look like they've been attacked by a bedazzler) and I'll just tell her straight up that her outfit is bad and tell her something else in the closet would look better. Luckily, we're both pretty blunt so neither one of us takes offense to pure honesty (or else I'd have a permanent 'mom smack-mark' on my cheek). You should suggest that you wish you could spend more time with her and take her shopping like everybody has posted. There's nothing better than a mom and her oldest daughter going to stores to try on clothes together. Let her browse around for stuff, and pick some stuff out for her that you think would look cute on her. If she doesn't feel like spending a lot of money, she doesn't necessarily have to go to JCrew/Banana Republic/Ann Taylor...TJ Maxx, Marshalls, or Nordstrom Rack always has some really good finds (and lately these stores been getting a LOT more designer items)! Good Luck :)
ckeller825 ckeller825 7 years
Sometimes my mom is the same way (dressing in leggings with some funky-pattern oversized sweater, or wearing jeans that look like they've been attacked by a bedazzler) and I'll just tell her straight up that her outfit is bad and tell her something else in the closet would look better. Luckily, we're both pretty blunt so neither one of us takes offense to pure honesty (or else I'd have a permanent 'mom smack-mark' on my cheek).You should suggest that you wish you could spend more time with her and take her shopping like everybody has posted. There's nothing better than a mom and her oldest daughter going to stores to try on clothes together. Let her browse around for stuff, and pick some stuff out for her that you think would look cute on her.If she doesn't feel like spending a lot of money, she doesn't necessarily have to go to JCrew/Banana Republic/Ann Taylor...TJ Maxx, Marshalls, or Nordstrom Rack always has some really good finds (and lately these stores been getting a LOT more designer items)!Good Luck :)
citizenkane citizenkane 7 years
My mother would KILL me if I knew she looked ridiculous and never told her. Ne honest, but not rude. Help her. Don't let her be a joke.
kikidawn kikidawn 7 years
How about just let her dress how she wants! I'm sure that you don't want her telling you to dress a certain way!Geez just let her be!
kikidawn kikidawn 7 years
How about just let her dress how she wants! I'm sure that you don't want her telling you to dress a certain way! Geez just let her be!
pink-elephant pink-elephant 7 years
I know a woman who does this...a friend of ours who's in her 60's but dresses like a 20 year old from the 80's!!
classicsugar classicsugar 7 years
runninesq - I was just about to say that! If she is truly petite, there are plenty of places to shop now -- Ann Taylor, Banana Republic, J Crew and many other stores offer petite sizing. (Trust me, I'm 5ft tall) Also, you can always have clothing tailored to fit if sleeves or pant legs need to be shortened. Agree that you should take her shopping. Let her pick out some outfits and you pick a few out that you think are more age appropriate. I'm guessing that as her one of her older daughters she values your opinion and would welcome some constructive criticism and compliments on good choices!
classicsugar classicsugar 7 years
runninesq - I was just about to say that! If she is truly petite, there are plenty of places to shop now -- Ann Taylor, Banana Republic, J Crew and many other stores offer petite sizing. (Trust me, I'm 5ft tall) Also, you can always have clothing tailored to fit if sleeves or pant legs need to be shortened. Agree that you should take her shopping. Let her pick out some outfits and you pick a few out that you think are more age appropriate. I'm guessing that as her one of her older daughters she values your opinion and would welcome some constructive criticism and compliments on good choices!
bengalspice bengalspice 7 years
I'm always buying things for my mom to gear her into a certain direction of what I think is appropriate for her age and for her sense of self-expression. My mom is always wearing what is cheapest to buy, not what makes her look like the kick-ass creative mom that she is.
runningesq runningesq 7 years
four words: ann taylor gift card!
Berlin Berlin 7 years
I'm having the same problem with my Mom lol. She's in her 50s and dresses like she's in her 20s. Some things are great, like i love that she wears hip bootcut jeans instead of those ridiculous tapered legs that so many Mothers wear, or baggy shorts with big shirts, and just blah clothing....she's an amazing woman who also ACTS and LOOKS like she's way younger. And I digress...there are somethings that while look great on a 22 yr old that just don't look best on her, while they make a young girl look hot and sexy, they can be too harsh looking on an older woman and actually AGE her! That's how I'm explaining it to my Mom. Some things are too young that age you more! That way you look older than you really are wearing something meant for younger. A good thing to do is take her shopping and make it all about finding sexy clothes and sophisticated goodness that make her feel beautiful and young, b/c that's all she wants, she just doesn't know how to get there. My mom just started dating this great guy who's more into casual suits and her backless sparkly tops just don't cut it. Her first outing with him she wore this very beautiful white long sleeve but Vneck (read: yummy cleavage cut) shirt with her boot-cut jeans. And she had a picture taken of the two of them and sent it to me, and she looked absolutely stunning. It was so simple but it softened her up and just made her look fresh and beautiful. And I got to rave about the photo to her and how what she wore really worked so well to her advantage, that its starting to show in her other clothes and she's realizing that she doesn't have to dress too young to look younger. Find celebrities (like Demi Moore! Perfect example!) that are older but dress younger and still look wonderful doing it, and let her see how she can model that.
Berlin Berlin 7 years
I'm having the same problem with my Mom lol. She's in her 50s and dresses like she's in her 20s. Some things are great, like i love that she wears hip bootcut jeans instead of those ridiculous tapered legs that so many Mothers wear, or baggy shorts with big shirts, and just blah clothing....she's an amazing woman who also ACTS and LOOKS like she's way younger. And I digress...there are somethings that while look great on a 22 yr old that just don't look best on her, while they make a young girl look hot and sexy, they can be too harsh looking on an older woman and actually AGE her! That's how I'm explaining it to my Mom. Some things are too young that age you more! That way you look older than you really are wearing something meant for younger. A good thing to do is take her shopping and make it all about finding sexy clothes and sophisticated goodness that make her feel beautiful and young, b/c that's all she wants, she just doesn't know how to get there. My mom just started dating this great guy who's more into casual suits and her backless sparkly tops just don't cut it. Her first outing with him she wore this very beautiful white long sleeve but Vneck (read: yummy cleavage cut) shirt with her boot-cut jeans. And she had a picture taken of the two of them and sent it to me, and she looked absolutely stunning. It was so simple but it softened her up and just made her look fresh and beautiful. And I got to rave about the photo to her and how what she wore really worked so well to her advantage, that its starting to show in her other clothes and she's realizing that she doesn't have to dress too young to look younger. Find celebrities (like Demi Moore! Perfect example!) that are older but dress younger and still look wonderful doing it, and let her see how she can model that.
hotstuff hotstuff 7 years
Why not just tell her? What's wrong with telling the straight up truth nowadays and not beating around the bush about everything? She's your mom she knows you love her and have her best interest just tell her she needs some new outfits and if you think she's having trouble picking out good ones tell her you'll go shopping with her! I would rather help my mom than let her run around looking a fool to her friends in 13 yr old outfits!
cubadog cubadog 7 years
I can't help but think back to when I was younger and my Mom tried telling me what to wear and how well that went over. I do not think your Mom is having a mid-life crisis wanting to say young does not mean she is in crisis mode. If your Mom wanted your input on what she is/has been wearing she would ask you. I id you do feel the need to stick your nose in her fashion business and it sounds like you want to it would be better to have her go shopping with a friend her age that has great style. I am guessing that you are not close to 50 and to be honest I think input from someone her age that has a great sense of style would go over much better than someone in her 20's or 30's even if you are her daughter.
petite42 petite42 7 years
Is your mom petite? You say she can swap clothes with the 13 year old, so I'm going to guess she's quite tiny. If that's the case, guess what....There's just NOT a whole lot of options out there for women who are over the age of 40 - especially if they are petite!!! Go visit a department store and see what I mean. Most of the more "mature" offerings are shapeless and, frankly, quite ugly. I'm 42 and wouldn't be caught dead in a lot of the clothes out there that are supposedly marketed for my age bracket. At any rate, I say mind your own business and keep mum about mom. Learn how not to be emarrassed by her choices, as they have nothing to do with you and are not a reflection on you. Unless she asks your opinion directly. If she opens that door herself, it's a different story. There are plenty of books and websites out there about dressing for your age. Most of them say there are few rules anymore, except wear what flatters your figure, and the older you are, the higher quality you should go for. But yes, 50 year olds can wear leggings and even minis - *if* their legs are nice!! If your mom doesn't look right in these, then it's NOT about her age. It's not about age-appropriateness - it's about figure-appropriateness. The other issue here may be that your mom remembers these styles when they came around the first time. She may be reveling in the fashions today simply because she loved them yesterday.
petite42 petite42 7 years
Is your mom petite? You say she can swap clothes with the 13 year old, so I'm going to guess she's quite tiny. If that's the case, guess what.... There's just NOT a whole lot of options out there for women who are over the age of 40 - especially if they are petite!!! Go visit a department store and see what I mean. Most of the more "mature" offerings are shapeless and, frankly, quite ugly. I'm 42 and wouldn't be caught dead in a lot of the clothes out there that are supposedly marketed for my age bracket. At any rate, I say mind your own business and keep mum about mom. Learn how not to be emarrassed by her choices, as they have nothing to do with you and are not a reflection on you. Unless she asks your opinion directly. If she opens that door herself, it's a different story. There are plenty of books and websites out there about dressing for your age. Most of them say there are few rules anymore, except wear what flatters your figure, and the older you are, the higher quality you should go for. But yes, 50 year olds can wear leggings and even minis - *if* their legs are nice!! If your mom doesn't look right in these, then it's NOT about her age. It's not about age-appropriateness - it's about figure-appropriateness. The other issue here may be that your mom remembers these styles when they came around the first time. She may be reveling in the fashions today simply because she loved them yesterday.
JaimeLeah526 JaimeLeah526 7 years
I'd try taking her shopping and helping her buy some new clothes. If she's picking up your sisters clothes to wear than maybe she needs more clothes. You can help her pick out stylish and age appropriate things that are also fun and flattering. Even younger looking styles could work to an extent if she got them in a more figure flattering size right?If that doesn't work than you need to tell her gently, preferably before you even leave the store, that people are staring at her outfits and that she doesn't need to dress young to feel young. Maybe it's time for her to experiment with a new look but that is not the one. Make sure you figure out what you're going to say ahead of time to avoid saying something you'll regret.
JaimeLeah526 JaimeLeah526 7 years
I'd try taking her shopping and helping her buy some new clothes. If she's picking up your sisters clothes to wear than maybe she needs more clothes. You can help her pick out stylish and age appropriate things that are also fun and flattering. Even younger looking styles could work to an extent if she got them in a more figure flattering size right? If that doesn't work than you need to tell her gently, preferably before you even leave the store, that people are staring at her outfits and that she doesn't need to dress young to feel young. Maybe it's time for her to experiment with a new look but that is not the one. Make sure you figure out what you're going to say ahead of time to avoid saying something you'll regret.
lickety-split lickety-split 7 years
i think you have to just let dina be dina, lol. do you want her telling YOU how to dress? if this is the biggest issue you and your sisters have with your mom she probably is doing pretty well. she raised the 3 of you alone and now that you're all at an age where she has a litte time to enjoy herself you want to tell her what to do. mind your own business.
lickety-split lickety-split 7 years
i think you have to just let dina be dina, lol. do you want her telling YOU how to dress? if this is the biggest issue you and your sisters have with your mom she probably is doing pretty well. she raised the 3 of you alone and now that you're all at an age where she has a litte time to enjoy herself you want to tell her what to do. mind your own business.
emalove emalove 7 years
I have never had this issue with my own mom, so I don't have much advice to give...but it sounds to me like she may be having a hard time turning 50 and getting older and is trying to keep her youth alive by dressing like a younger woman/teenager. She probably doesn't realize how silly it looks. Maybe you could go shopping with her and suggest some pretty, age-appropriate looks for her?? Keep telling her how good they'd look on her, that sort of thing. You don't want to hurt her feelings.
jaxon jaxon 7 years
Take her shopping, tell you sisters to do their own laundry, and put locks on their closets. You might have to face the fact that she may never dress differently. She thinks she looks good and may continue to do so no matter how you feel.
jaxon jaxon 7 years
Take her shopping, tell you sisters to do their own laundry, and put locks on their closets.You might have to face the fact that she may never dress differently. She thinks she looks good and may continue to do so no matter how you feel.
j2e1n9 j2e1n9 7 years
See, this is how I think Lourdes must feel about her mom, Madonna :OY: I would nominate her for a makeover show! After all they are the professionals and she will truly see that she will actually look prettier and younger by dressing for her age.
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