Ask A Woman: Dressing Your Age Part II
If you’ve got a question that needs the female treatment, chances are you’re not the only one who wants to ask it. Beth is our source for the answers. From opinions on men’s style to decoding the sometimes mysterious ways of women, she’ll take on a different question every Thursday. And don’t worry, your identity will be protected too. Click here to get to know Beth, then get in touch with her by sending your question to: askawoman@dappered.com
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Miss Beth’s first installment on dressing your age? She’ll reference many of your comments you left under that post. So click here to get caught up.
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Hi Fellas,
Last week we began a discussion on age and style, and we got some great comments, so let’s keep talking. Three major questions were raised, and we’d all love to hear your answers. Let’s get started…
#1. What are you looking forward to wearing as you age?

I’d said that I have my own ideas about how to gauge whether or not your style is “appropriate” for your age. Note who you’re looking to for style inspiration. If you’re 35 and asking your barber for “the Biebs,” you may want to reconsider your style choices. (By the way, Donny Osmond totally rocked that look in the 70’s, so let’s give credit where credit is due, mmm?) And as Raymond wisely pointed out last week, this goes both ways:
“As a 20 year old guy, there’s some things I’m actually waiting to get older to wear (at least on a regular basis). This mostly pertains to hats such as fedoras, etc, as I feel like at my age it’d come off as nerdy, or even worse, hipster-y.” – Raymond
If you’re 25 and you’re scouring the Internet to find out where Bob Barker buys his blazers, you may need to wait a few years. Like Raymond, are there styles you’re looking forward to wearing after you’ve aged a few decades?
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#2. Does level of fitness contribute to how long you can pull off younger looks?

Several people mentioned attitude and body shape being a more important determinant of what you where than age. But attitude and body shape are not necessarily requirements for young people to dress with style. There are plenty of younger folks who don’t have slim physiques but still dress fashionably. It seems like that would indicate that with aging there still comes more restrictions for fashion–yes, you can where trendy styles, but only if you maintain a fat-free frame.
“Honestly, I think fitness and energy matter more than age. If you are 50 and have the shape and face to wear slim jeans with an oxford shirt and tie, then do it.” – Stephen H
What do you think of the theory that you can wear styles aimed at younger folks when you’re older, as long as you remain active and trim?
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#3. Have you started to ask yourself what is and what is not age appropriate?

Matt says he doesn’t think about age when he’s dressing…but I wonder if that’s because, at the age of 23, he’s young enough that he doesn’t have to wonder yet if his clothing makes him look ridiculous.
“I’m 23. I don’t really think in terms of age when I’m deciding what to wear. Every week day I’m in a suit and tie for work. My clothes are tailored and fit me well, so that might make it youthful.” – Matt
I myself am older than 23, and in the last year or so, I’ve found myself thinking twice before I purchase a new garment–is this age appropriate? It’s a new consciousness for me…and I have to say, it makes me feel a little uncomfortable. Anyone else out there second guessing their purchases as they age?
Okay guys, round two on age and style–let’s hear what you have to say.
-Beth
Got a question for Beth? Send them to: askawoman@dappered.com
First, thanks for being the voice for women here. Its been enjoyable to read your weekly responses. Here’s my question. Are there any zero tolerance, deal breaker things that if a guy is wearing a woman won’t give him a chance? I’m thinking bracelets on guys. No? And is there anything else?
Chris
I turned 40 this year and I’ve only just started trying to dress like an adult. And now that I do, people aren’t sure what to think. There are some styles that I couldn’t (and wouldn’t want to) pull off, but I think having a young-looking face and a slim body definitely helps widen the range of acceptable clothes.
I think the key is to dress with style, as opposed to fashion. There are certain essentials of a mans wardrobe, that when well tailored and of a decent quality, can transcend age. Maybe I play it a little too safe, but I feel if you feel that something isn’t age appropriate, then maybe it’s just too trendy for any age. An Affliction shirt isn’t age appropriate for a fifty year old (even though some still seem to wear them), but a well dressed 20 year old wouldn’t wear it either.
Basically, I just feel that if you stay away from trends and stick to classic mens style (as this site so often proposes) the age appropriateness isn’t really a factor unless you are very young or very old.
I completely agree! There are plenty of young people and old people who don’t just dress ignorantly of how they look, they actively dress in a ridiculous manner. As long as the fit is spot on, 20 year olds and 50 year olds can essentially wear very similar things, as I see it.
Cheers,
Ben
I’ve found that when you are in your 30s t-shirts are more of a weekend around the house or I want people to know it is really casual sort of garment. Sweaters, button downs, and polos are more the standard.
Beth… You forgot to mention that in addition to be young, I’m also hot and radiate self confidence. I can look good in anything.
Anyway, I agree with ttfireman and Ben, style is really what matters. And well made stylish clothing is really ageless.
-Matt
At 30 I have an increasingly difficult time going beyond the front yard in a Tshirt even on weekends. And it’s true that fit guys have more leeway within the age appropriate style range. When a fit guy wears a nicely fitted Tshirt he looks crisp and as though he takes care of himself, which is respectable and shows that he is in control of his world, attributes that are expected of us by 30 plus. This all compensates for the otherwise casual look. Agree?
I think you CAN take more care with your appearance, and dress “up”more in everyday contexts, as you get older. Suits, ties, hats, etc. won’t seem as pretentious on an older guy as on a younger guy. On the other hand, lots of older guys show up in the pajamas because they just don’t give a rip any more.
In Section #2 with Brady, you use the word “where” instead of “wear” a couple of times.
Good Work, You have done a great job. Thanks a lot for this precious post
I totally agree that the individual should know their body. Understanding what is flattering on your body is also the true understanding of style and why the existence of sites like dappered is necessary.
I also agree with the delineation whether the item is stylish or fashionable is a key factor in determining whether or not the item is “too young/old” for the individual.
But then I also think the disagreement then boils down to what the definition of “style” is.
Is style more relatable to general lifestyle, or is it based off of the situation?
It is my belief that it is the specific situation.
For instance:
Is it acceptable for a younger or older gentleman to wear a nicely fitted white T-shirt, blue denim jeans, with a pair Chuck Taylor Allstars to a wedding?
Or is it acceptable for a younger or older gentleman to wear a French cuff shirt, black tie, a three piece charcoal suit with a pair of black wingtips to a superbowl barbecue?
These are certainly extremes but I think that we can agree it is the situation determines how appropriate our attire is which then dictates whether or not .
Then if I was to ask you each individually imagine what a young teenager from 13-16 was to wear, followed by what a young gentleman, and then finally what an older gentleman would wear.
The outfits are probably a standard of what you think is most important in the daily life of the age group.
For example:
The teenager playing sports/being rambunctious (I know this is a very young male gender stereotype)/and not looking for a career maybe a job/internship.
The young gentleman working out/dating/career hunting/working.
The older gentleman probably not as active/married/set in his career/retired.
If we were to strip away our preconceived notions of general situation and focus on the specific situation the teenager, younger or older gentleman was facing such as: a date, an internship/job/career interview, a work out regimen: playing sports with friends/weight training/simple aerobic exercises, etc.
Maybe the statement of an item being either “too you/old” is more of a statement it no longer fitting any possible situation you are facing in the near future. Or the item is simply not “stylish” it is a “fashionable” item.
Ever since I was a kid (I’m 57), I’ve felt that true “style” was best exhibited by taking a current look, relaxing it a bit, and carrying it off to an appropriate venue. When exagerrated bell-bottom pants were popular, I thought the truly stylish wore less-grievous “flares” ( the latter soon became mainstream, and were worn apppropriately nearly everywhere). There is a fundamental difference, in my opinion, between fashion and style: The current skinny-jean thing (fashion) thus gives way to slim-fit (style), and style is ALWAYS age appropriate.
But then Warhol said “if you dress old when you’re young, as you age you look the same”.
As a 33 yo woman, there is nothing worse than meeting an older man for a date when he’s trying to look my age. I’ve dated several men in their 40s that were fit, but tried dressing my age to show off how young and vibrant they are. I get it, but it also makes me wonder how insecure they are with themselves.
I am 24 and there are days I fret about time slipping away and my getting older (very few of my friends are older than me). I love to shop at stores like Express (I emailed them concerned the mysterious banishment of the Signature Polo) but do worry how long till I will no longer feel comfortable shopping there. I suppose I have a number of years left as many people think I look young for my age but I dread the day when I must abandon that place. I am hard pressed to find exact styles and fits that work for me and Express was my greatest find in that regard. I usually try to dress well when going out but that can be simply choosing the right “causal” shirt, matching colors, and adding say a scarf or something to the ensemble. I think you just have to use your best judgement for the occasion, not fearing being a little “out there” but knowing when it would look better on someone half your age or twice your age. Perhaps trusting your gut when assessing what kind of audience a store (like Express) is aiming to advertise/provide products to.
I think context is important. example, the setting is a date, or going to a wedding, funeral, work etc. Seems like everyone agrees you need to dress appropriately for certain situations. But more important than fashion, I think, is style. owning the style and being able to express yourself confidently is what makes the look. your style of dress is like an expression of your personality through clothes. And your style will shine through in your wardrobe by the types of clothes you choose to buy and wear no matter what the setting is. That said I don’t think age is really important.
Another thing to remember is people will always be making negative judgements. Everyone has different ideas of what looks good/appropriate etc. And if you’re selfconscious about how a piece looks then maybe it doesn’t fit your style regardless of your age.
I’ve seen some over weight people squeeze into some skinny jeans that look like they were painted on. It makes me cringe but they seem to be comfortable with themselves so whatever. It makes the world more interesting. I’ve also seen some people who are in horrible shape but when dressed up look like a million bucks, so I also don’t think that’s too important. btw how we take care of our bodies, exercise, haircut, makeup, etc is also a reflection of our personality just like clothes. this is turning into a rant so Im gunna end here.
I’m in my thirties, but I am told constantly that I look much younger (people sometimes think I’m my eleven-year-old stepson’s older brother). I’ve no real expectation of looking more mature any time soon based on the fact that my mom looks 20-25 years younger than she is. So most of the time, when I dress “my age” I feel like I appear to be playing dress-up, and when I dress a little younger I just feel a bit out of place picking my boy up from school.
I’m 31, I look in the mirror and I dress for me by coordinating my eye color with the fabric and it’s drape with my bones. That’s about it.
I ask nothing from society. Especially not it’s opinion.
I get everything style is supposed to provide just by not giving a ****
I suggest more people not give a ****
Let’s make not giving a **** a style.
Imagine a world where people were allowed to express their individuality on their bodies instead of their sheep like ability to blend in… That’s a beautiful world.