How Not To Dress Old, Part 2: Old Clothes vs. Young Clothes


I’ll admit it. Clothes can be confusing.

Stop me if you think that you’ve heard this one before. When I was 12, back in the 1980s (yes, I am that old… thanks for not noticing!) I found a plaid power suit in Vogue and begged my immensely talented mom to make one for my 50-pound body. I wanted the total look: the shoulders, the hair, and most of all, the hips. I wanted the curves and the swagger of a woman twice my age.

The curves never did come. The age, however, has arrived.

Today, I no longer want to look older, but I don’t want to look 12 again either, or even 22. I want my apparent age to fall into that vague, undefined period between grad student and grandma. Okay, maybe that’s too broad. Let’s just say I no longer aspire to look like I’m in my 20s, but I’d like to look like I am 30-something pretty much forever.

And to do that, I’m going to need the right clothes.

Before I go on, let me just state for the record that if you are a young mom in your 20s, you can wear pretty much anything you want. Anything. And if you’re early 30s and look like you’re 20-something, you can still wear pretty much anything you want. After that, the rules change a little. I covered a few of them here, and here’s a follow-up. Fortunately, learning how not to dress old is simpler than you think!

Let me illustrate. First up, this silky mustard-colored Thakoon blouse.



This blouse may look innocent enough, but it should come with a warning label.

And so should this blouse:


And this suit:


These are all examples of old clothes.

In your 20s, they’re IRONIC.

In your 40s, they’re AGING.

In your 70s, they’re ELEGANT. (Except for that middle blouse. No redeeming value there.)

The difference (and forgive me if I repeat myself) is in the details. Cut, color, and fabric all play a part in making an item look too-something.

Here, a few more examples:

Too Old


This is an understated version of the mom jean, and because it’s a little bad and not deliberately bad, like the faded, super-high-waisted trendy mom jeans that are so trendy right now, it’s instantly aging. Another word about mom jeans. If you’re a mom, don’t wear them. The irony is lost, in my opinion, and no one needs to look shorter or lumpier than they are.

Too Young


Just Right


Notice the jeans that I dubbed “just right” are still youthful and fresh and a little edgy. Some of you may find them too trendy, but in my opinion, this is an acceptable level of trendiness without veering into frumpy category category.  (Another note about hip jeans for moms. You’ve probably heard me go on and on – I do like to hear myself talk! – about the absolute need for every single woman over the age of 20 to own one sleek, slim/skinny/straight pair of clean jeans  with no rips, tears, fading or whiskering in a dark, even denim wash. They can be dressed up and down and are oh so flattering, yada yada. I favor the perennially popular AG Stilt, but after you invest in these basics, a more relaxed, slightly distressed boyfriend style is next.)

And now, a word about dresses. Some dresses are instantly aging and awful in an obvious way, like these:




Others are not so obvious. Check out these examples:

Too Old


Don’t let the snazzy styling fool you. Taken separately the details (midi-length, drab print, droll little ruffle jacket) are questionable but not catastrophic. All together, they add up to a mess.

Too Young


Too many trends, all at once, in a shape that is entirely too sweet, make this dress a disaster for anyone over the age of 21.

Just Right


A bold color, flattering length and contemporary cut all add up to great style.

Still confused? Here’s a little trick: Pick the right brand, and then choose a silhouette that is right for your body type, and you can’t go wrong. What are the right brands? Here, a cheat sheet.

Old Brands

Alfred Dunner, Chico’s, J. Jill, Lauren Ralph Lauren and Joan Vass are all geared towards an older customer, but other brands, like Eileen Fisher, Chaus, Donna Morgan, Talbots and Lane Bryant have been updated and now offer a wider array of styles, so when in doubt, refer to the guidelines above!

Young Brands

These will come as no surprise, for the most part, but stores like Urban Outfitters, Forever 21, Arden B, Bebe, Windsor, Abercrombie, Hollister, Aeropostale and any of the inexpensive trend stores (DOTS, Rainbow) all cater to very young women, and are the age equivalent of the Juniors’ section of a department store. Other stores, like Uniqlo, Topshop, H&M, Old Navy, Victoria’s Secret and Target, appeal to a wider demographic, so the distinction isn’t as clear. Refer to the pointers above. 🙂

Just Right Brands

Anything in the “contemporary” department  usually falls into this category, as well as specialty retailers like J. Crew, Loft, Ann Taylor, Banana Republic, Zara, Anthropologie, Kate Spade, and Tory Burch.

Still confused? I’ll sum it up this way: Shop the right brands at the right stores, and avoid extremes (too short, too tight, too trendy), and you’ll make the right choice every time! Did I miss the mark on any of these? I’d love to hear your thoughts!


  1. Megan says

    Thank you for this great advice!! I’m 31 (soon to be 32) and am at a strange turn in my life where the clothes I have are starting to not seem so age appropriate. Time to go shopping I suppose!!

  2. Gwen says


    I’m actually 55 and still want to dress cool and young without being frumpy or by trying too hard. You are right on.J.Jill is too old and Forever 21 is too young. Quality and cut is very important once you hit 35 Love your blog. Gwen

  3. Honi says

    The most challenging part is being 55, in good shape, and not wanting to look old. I also don’t want to look like I’m wearing my daughters clothes. There aren’t a lot of designers who hit this demographic just right!

  4. says

    I soooo agree Honi! The clothes are either too old or too young, for the most part. Some lines that I feel usually have options for stylish women in their 50s include, Theory, Eileen Fisher, Sundance, etc. but honestly my style is really going to stay very much the same as I transition into my 50s, but with a few tweaks. I will be wearing Karen Millen, Ted Baker, Kate Spade, Diane von Furstenberg and other fun, colorful styles for as long as I am able, and I think if you are fit and take great care of yourself, you should do the same. 🙂

  5. Cindy in Florida says

    I loved your article and you were spot on. I am laughing because I see woman in their 40s and 50s wearing a bikini and it makes me cringe. I am in that age group and v try physically git, I would die before wearing a bikini. What are your thoughts?

  6. says

    Yay. Nice to hear from a fellow Floridian! I am torn on this. I think the problem is confidence. I believe that if you have the body type and are fit enough to pull off a bikini, then that is great, but the bikini style shouldn’t be the exact style you wore at 20. I agree with you, though, that I cringe because so many women wear them and are clearly not comfortable in them, and that lack of confidence shows. A really stylish one piece would be much more flattering in that case. 🙂 I am in the same age group and definitely pick one pieces these days. LOL

  7. Judith says

    I just turned 70 and have purchased a bunch of colorful clothes and it’s been so much fun. I think a person who isn’t overweight has way more options at any age. I was a super hippie and I’ve brought back some elements of boho to my wardrobe to add interest. By the way 70 is fun – retirement means freedom from ‘work clothes’. One of the highlights of my day is choosing an exciting outfit from my closet just for me!
    P.s. I still have my red hair (with just a touch of grey) and I wear jeggings and funky wedgies (Flys).

  8. says

    Hi Judith! Thank you sooo much for this comment! I am positive that it’s going to inspire other women as it has me! I love that you have chosen to embrace color and return to your true boho style at this stage of your life, when you have the freedom to dress as you want. Thanks for sharing this! Please share a picture when you get a chance! I’d love to see one of your exciting outfits! God bless. 🙂

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