Dress Your Age Not Your Shoe Size

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I hate too many rules with fashion – it takes the fun out of it. I don’t think a certain age requires one to have a certain length of hair or skirt, and heck, I think diamonds are too pretty only to wear in the evening and when older. However, I think some fashion guidelines are created to help us. As they say, dress your age not your shoe size.

I was crossing the street in Washington D.C.. In front of me was a woman in a full-length mink coat and a shoulder-length sandy-colored bob. She wore black pants and heels, had a very large black handbag, and was walking purposefully. From the back, I assumed she was a successful and powerful woman in her late 40s to early 50s.

At the intersection, she went left when I went right, and I was able to see the front of her and was utterly shocked to see this woman was, in fact, younger than I – probably in her early to mid-20s with a fresh face and a baby pink cashmere turtleneck.

This weekend, I visited Miami, the land of flamboyant dress. I saw so many women of all ages strutting their stuff – be it money, creativity, fashion sense, or love of a Bedazzler. What made many of these women great was that they wore their confidence as loudly as their gem-encrusted lounge suits.

It isn’t my desire to wear lamé tunics and appliquéd jeans, but I respect these women’s desires – their style is appropriate for their environment and lifestyle, and most had colors that flattered, cuts that fit, and accessories to tell a little about the woman inside.

However, I did also see quite a travesty while on my vacation – women dressing as children. My sister and I saw a woman at the Bal Harbour Shops in a pink spandex tube top riddled with beading and sequins, a white cotton ruffled micro-mini skirt, pink metallic wedges to match her pink metallic lips, and extensions that put Paris and Brit to shame. It had the look of a Bratz doll and was being worn by a woman in her 40s. There was nothing wrong with a passion for pink and all things girly, but on this woman, it looked like a costume… and it looked ridiculous.

Later, we saw a woman with her children with a teased ponytail on top of her head, sequin-embellished cropped jeans, metallic heels with satin bows on them, and pink glitter all over her eyes and lips. Her daughters were dressed similarly – too cute on a four-year-old but a bit desperate on the 30-something mom.

Dress Your Age Not Your Shoe Size

No one is saying you have to toss your Levis for wool gabardine once you hit 40, or that only “ladies of a certain age” can wear jewels, it is just being true to yourself. A four-year-old dresses in what is shiny and fun, not needing to find clothing as a uniform, a social norm, or a communication device. The older we are, the more our clothing multi-tasks and extends our personality and lifestyle. Our wardrobe needs to be as multi-faceted as our personality.

Just as I recently mentioned of animal-shaped hats and cartoon tees, wearing clothing too old or young for you confuses those who meet you, not understanding your true nature and often pre-judging you.

  • Dressing too adult can make you seem boring, old-fashioned, unstylish, and uptight.
  • Dressing too young can make you look unintelligent, superficial, promiscuous, and annoying.

It is possible to seem youthful and creative without raiding your daughter’s closet and to look classic and conservative without dressing like your mother.

How to Add Youth to a Conservative Wardrobe

Play with Color

Instead of donning neutrals and black, add some cheer to the mix. Pastels are feminine and subtle and great compliments to gray, camel and brown. Jewel tones like berry, teal and plum add class to a simple look and flatter most any skintone.

Walk the Mall

We often get comfortable with the brands we shop at; maybe we choose Boutique B because they have conservative hemlines and classic lines. The thing is you can often find items that fit your sense of style in unexpected shops. A classic pencil skirt could be found at Old Navy, a great suit in J. Crew, a lovely trench in Bebe. Be honest with the salesperson about your style and needs so you don’t waste either of your time.

Keep it Simple, Sweetheart

Keeping your hair and makeup simple, clean and fresh will help show your youthful side. Over-polished hair styles and matte makeup ages anyone.

How to Make a Whimsical Wardrobe Age-Appropriate

Consider Proportion

If you do a short skirt, balance it with a top with volume and/or a chunky shoe. If you do a whisper of a top, balance it with a full skirt or trousers. Baring the belly? Add a bit of fabric elsewhere to keep the look proportional. This isn't about covering up, it's about accentuating the positive and turning your ensemble into art.

Channel Chanel

Coco Chanel once said, “Before leaving the house, look in the mirror and remove one accessory.” No one would ever find Chanel to be boring or fitting a mold. If you have on bracelets, large earrings, several necklaces, sunglasses, six chunky rings, a hip belt, a scarf and a headband… you look like a fashion victim, not an artist. You can still show your sense of whimsy or creativity with less embellishment.

A strong necklace can be far more telling than a ring on every finger, a great bangle made by an artist or picked up on vacation holds far more interest than a mess of necklaces from any old mall store. You will receive more compliments and inquiries into your look or accessory if it gracefully holds the spotlight and doesn’t fight for it.

A woman with curly hair wearing a plaid blazer holds a green fur coat over her shoulder on a city street.

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  1. Hi Chris! On my phone, will try to answer all 🙂
    Piecey is when hair has obvious layers, look up Lisa Rinna onbGoogle Images, she has a piecey do & uses Jonathan Dirt for it (a pomade-like product by stylist Jonathan Antin, sold at Sephora). Yes, lowlights are darker streaks which give hair the look of depth. H&M is a Scandanavian retailer who came to the US a few years ago offering popular trends & occasional designer collaborations for low prices (me, women & childrens clothes). Hm.com but the stores are huge like a Tj Maxx or kohls. For a suit, try Lane Bryant who does stylish simple pieces, lengths, they even have online & stalk their sales for a good priced suit. While black may not be your best, it’s far more versatile & gray may be a better alternative (and easier to find & look more expensive). And sadly that woman was a woman and in that part of Miami, the norm 🙂

  2. Allie,

    I know that you’re busy with your sister at the hospital.  So answer whenever you can get to it. If that is a period of weeks, that’s fine. The main thing right now is to take care of your family and yourself. I hope that you are eating, staying hydrated, and are resting.

    I have a number of questions for you. I am so far out of the style/fashion world that I’m not even in our solar system so don’t be surprised at my dumb questions.

    – Referring to hair, what does piecey mean?

    -What is Johnathan Dirt and what does it do for hair?

    -What are low lights? Are they strands of hair that are darker in color than the rest?

    -Store name H & M? I’m not familiar with it. It is a women’s clothing chain?

    -You refer to low quality suits. What should I look for in a suit? I am a plus size, 5′ 9″, fairly well proportioned, long legs. I’d say that I have an hourglass figure, just a jumbo one. Unlike you, I look awful in black, at least near my face. Black pants or skirts are OK. But if it’s a suit, don’t I want the pants or skirt and jacket to be the same color? Navy is a good color for me. Is it possible to get a decent suit for $50 or less? If not, $100 would be my absolute maximum. Recommendations please. I need help.

     A quote from one of your posts and my comment –

    “My sister and I saw a woman at the Bal Harbour Shops in a pink spandex
    tube top riddled with beading and sequins, a white cotton ruffled
    micro-mini skirt, pink metallic wedges to match her pink metallic lips,
    and extensions that put Paris and Brit to shame. It was the look of a
    Bratz doll and was being worn by a woman in her 40s.”

    Now, a little humor. At least I hope you take it that way. Are you sure
    that this person was not a cross dresser? Some of them wear outrageous
    outfits. On the other hand, some cross dressers have such a refined
    sense of style that you wouldn’t know she is a he unless you are a
    personal friend.



  3. Fashion is fun and I have always loved classics with signature touches. As I approach a big birthday, I feel the need to step it up and invest in some special things for my wardrobe, a chic cashmere cardigan, some new fitting pants and a party dress. I love fashion and always will!!! Nice list or guidelines.

  4. Body, lifestyle, and personality appropriate are all that matter to me. Dressing shouldn’t be about all these rules relating to what Who is to say what is despearate, too young or old, or inappropriate? Why should the person dressing themselves for personal expression even care what you think? I thought fashion was supposed to be fun not fascism.

  5. I’m 25 (26 in 2.5 weeks!) and I wear diamond studs everyday and have NEVER owned a skirt more than an inch or so over the knee. I don’t think I look older than my age at all. I enjoy diamonds and classicly cut clothing. I do wear fun colors and prints and I showcase my decolletege when appropriate (decolletege, not 3 inches of cleavage:)) I agree that not all fashion rules should be followed, but a basic framework of ‘guidelines’ to keep it age-appropriate and classy is important to keep in the back of your mind. I love your style!! Keep it coming, we’re all eating it up!

  6. Thank you Allie!!! Some people claim that dressing in loud, short, cheap clothing makes them happy – they say this until they actually put on nice clothes and see how classy and appropriate they look in a more toned-down, age appropriate style. So many moms say they love to wear younger styles and even more moms say they like dressing …. dumpy. Put them in a classic outfit and in a pretty color and most will never go back.

  7. You know, the age/shoe size saying gets much more complicated if you go with European shoe sizes 😉

    I say pile on the accessories, like Chanel actually did!

  8. I think Coco might tell me the opposite. I don’t think I use accessories enough. Typically I just wear my engagement ring and maybe earrings.

    Great post. I wish I could send it to my 50-year-old aunt who dresses in Uggs (gross), mini skirts, and halter tops (yeah, that’s all one outfit).

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