Style Over 40: Am I Too Old to Wear This?

Every few months I see a variation of this scene on social media: a scantily clad woman dancing around in a revealing outfit, complimenting her own physique, and saying she can wear whatever she wants at age 60. For the record, I'm not sure whether I'm seeing one or multiple women here and I don't know her/their exact age. It doesn't matter. She's boldly flaunting the societal expectation for women her age. She's thin. She's hot. She looks just as good as a woman 20 or even 30 years younger than her.

Displays like this make me think, "We've totally lost the plot on 'age-appropriate' dressing". It's become a race for the bottom (or showing bottoms?) and seemingly endless comments about not wearing anyone's expectations. Godspeed to the partially nude sexagenarian. I wholeheartedly agree women over 40, 50, 60, and beyond shouldn't feel pressured to conform to arbitrary societal expectations about style and fashion. At the same time, shouting from the rooftop in your underwear about defying said expectations isn't giving confidence to me, but what do I know?

The frustrating part of the how to dress over 40, age-appropriate dressing, public conversation is it pretty much always circles back to how much skin you're showing (or not showing). As if showing (or covering) a certain percentage of your body or wearing a particular hem trigger a scoring mechanism that changes with each decade of age we achieve. [A note: I suspect (but haven't confirmed) there's a corresponding criticism for younger women dressing too mature for their age, i.e. "You're so young! Better flaunt it while you can!" Even though that's not the focus here, I'd offer similar questions as below to those younger women as well.]

I say public conversation because I talk with clients, the majority of who are over 40, all the time about how to dress for your age. We aren't breaking it down by body part. Instead, we're focused on the messaging and impact associated with the looks we're creating. Forget societal expectations. What are your expectations with respect to dressing for the event at hand? How do you want your outfit to be perceived by others? Are you concerned with whether your ensemble could detract from your accomplishments? No doubt the wearer's age is part of the discussion, but it's not the way you might think.

Instead of asking whether an outfit or piece of clothing is too youthful, too revealing, or if you're just too old for that, ask this instead:

First, who's the audience for your outfit? Spoiler: the answer is not yourself unless you're dancing around your house alone drinking wine while wearing the micro-mini in question.

Like it or not, what you're wearing is the first thing people see, even when they already know you. Consider who you'll be seeing and the context in which you'll be seeing them. Dinner with your husband on an island vacation is different than dinner with your husband and his work colleagues. Saturday brunch with your girlfriends from college is not the same as Saturday brunch with your in-laws.

It's not about dressing like someone you aren't or in a performative way; it's about dressing in a manner consistent with the position you're in at that moment.

Second, if you're in a leadership position (including as a mother or maternal figure), is your outfit consistent with the example you want to set? Oof. I definitely didn't think about this one when I was younger. You probably didn't either. The older you get the more likely others are looking up to you.

Your daughters and sons (for me, nieces and nephews) are most assuredly taking note of how you choose to present yourself and the example you set. Similarly, at work, those who answer to you or those who you advise evaluate you professionally, in part, based on your appearance. When I practiced law and didn't feel like getting dressed, I would remind myself that if I didn't look like I could take care of myself, a client might question whether I could solve their problems.

Dressing for leadership, whether personal or professional, involves setting an example for those who look up to you or strive for similar accomplishments.

Third, will the outfit you've selected detract from what you're trying to accomplish? This is an especially critical question to consider in any professional setting. The lines can feel especially feel blurry and fraught for women because let's face it, the guys are just going to wear some version of pants and a shirt.

As a former lawyer who loves style and enjoyed planning her outfit for the office holiday party, I know this is a fine line. You want to wear something that at least partially reflects the out-of-the-office version of yourself, but you also don't want anyone to lose sight of your professionalism. The truth is I still take this into consideration as a personal stylist. I want clients see I'm a personal styling expert and professional based on how I dress; at the same time, I don't want them to feel overwhelmed or intimidated in a way that would prevent them from candidly sharing their style struggles with me.

Even if you're working at Vogue, you still want your professionalism and competence to be the focus of your working relationships. You can absolutely dress like a stylish boss while you do this, just make sure what you're wearing doesn't take away from the work you do.

It's not just that our outfits or style hits differently after 40.

The considerations that go into how we dress as we age are multi-faceted. There are many questions that come up in styling sessions on this topic beyond those above. Unfortunately, the typical conversations about dressing over 40, style over 50, and (my favorite lol) midlife style, lack nuance, context, or a neutral framework to guide actual decisions.

Let's reclaim age-appropriate dressing so the focus is on good judgment and ensuring you dress in way consistent with your personal style, roles, accomplishments, and goals. Selecting outfits based on your actual life circumstances will leave you feeling more confident than attempting to follow an arbitrary set of societal expectations. I don't know about you, but I'd much rather make my own rules than dance in my underwear on social media to break someone else's.