The short answer is no.  Middle-aged fashion is not a thing.

One day not long ago, I googled “What not to wear over 50.”  As you can imagine, there were a gazillion articles about all the things women our age should NOT wear for fear of looking foolish or desperate: clothes that are too baggy, clothes that are too tight, clothes that show too much cleavage, fishnets, thigh highs, ankle boots, bikinis, bathing suits with skirts, PJ bottoms out of the house (excuse me?!), etc… a list as long as your arm.  There are also articles on how we shouldn’t give a fuck and should wear whatever we want (so let’s be clear: PJ bottoms out of the house are a GO!).  But it really made me wonder: as our bodies change with age, are there clothes that are more flattering?  Is middle-aged fashion a thing?

The short answer is no.  Middle-aged fashion is not a thing. There’s not a single fashion magazine for women our age.  Vogue’s readers are mostly between 16-34 and Elle’s target audience is 16-25.   Almost all designers are creating clothes with twenty or thirtysomethings in mind; we’re simply not the target audience.  Eileen Fisher, arguably among the most polarizing women’s fashion designer in history, is the sole exception. Women either love her clothing or hate it — think flowing linens, drawstring pants, boxy caftans — but you can’t deny that at least she truly cares about our demographic.  Racked described the Eileen Fisher/Diane Keaton look as “menocore” — normcore for the menopausal set (ouch!):The Eileen Fisher Woman has aged out of the male gaze without a backward glance, and she is totally at ease in her body. She exudes self-acceptance and self-actualization and all the other self-based issues we struggle with in our youth.”  Preposterous!  Why can’t we be comfortable and wear what we want without it being contextualized in terms of its desirability to men?  (And, if we were going to analyze it that way, Diane Keaton caught the gaze of some pretty hot men. Warren Beatty anyone?!)

I used to care a lot more about what I wear than I do now.  In my younger days, I worked in retail and it was important to follow design trends and wear them.  When I was in law school, I wore combat boots with vintage dresses and lots of crazy jewelry (picture Madonna circa 1987).  Later, as a lawyer, I had to look polished and professional while still maintaining my own sense of style, so, when I had to wear a suit, I always made sure I had a fabulous colorful purse and interesting shoes.  These days I work from home and comfort has become my priority, but that’s not to say I’m without vanity. I still want to look good, and finding things that work has definitely gotten harder as my body has changed (three kids, menopause, a love of carbohydrates).  

So, I asked Irish fashion designer (and Woolfer!) Daryl K for some advice. Daryl has been making downtown New Yorkers look fabulous for decades.  She reached cult status in the 1990s and maintains it to this day. I asked her whether there are things that look better, work better for women our age?  Happily, her answer was yes!

Daryl explained that rather than thinking about fashion, at this age we should really be focusing much more on fit and fabric.  By this point in our lives most of us have developed our own sense of style, know what we like and don’t like, and for the most part, we can stay true to that. What becomes much more important as we age, Daryl says, is paying attention to high-quality fabric and cuts. Cheap and easy solutions are no longer as easy to pull off.  She suggested avoiding jersey tops (I was wearing one at the time) because they cling where you don’t want them to (looking down, I saw she was correct) and while they look good on the hanger, they are not the most flattering with any kinds of bulges (back fat, muffin top, batwings). She suggested button down shirts — button down, woven, silk or cotton.  Pick up the hanger, she suggested, and see how the fabric moves. Spend a little more; it’s worth it. Even a t-shirt, she noted, can be well fitting. It’s not just the design, but the fit. As for pants, she suggested a skinny rather than a wide leg (phew, I had those on).

ICONC Daryl K Leather Leggings

I’ve taken Daryl’s advice.  I invested in some beautiful long sleeve silk blouses and some button down shirts (they are a little pricey, but I love Rails, especially if you’re busty, as I am).  I still wear them with my mom jeans (and my ankle boots), but they feel good on me and I feel good when I’m in them. Like many women my age, I have pared my wardrobe down to those things I know work for me.  In the winter, it’s jeans with a cashmere sweater or a button-down silk or cotton shirt with boots. In the summer, I stick to dresses with sandals. I know many a Woolfer who lives in Daryl K leggings while others swear by the Commando faux leather leggings. Some women (like Nina for example) have a list of things they’ll never wear.  I find it easier to stick to my basic uniform.  For me, middle-aged fashion is now a great fit, lovely fabric and wearing whatever the hell I want.  And, yes, I still leave the house in my PJ pants. I’m just not wearing a jersey top when I do.

To hear more on this topic, listen to our podcast episode on fashion where Nina and I discuss these matters in more detail with fashion designer Daryl K, here:

Tags : fashion
Hillary Richard
Hillary Richard is a recovering lawyer who has an opinion about almost everything. And she’s usually right.