How to dress like yourself when you don’t feel like yourself
Age, relevance, and reforming my style from the ground up
Lately I’ve been thinking about how to dress like yourself when you don’t really feel like yourself. Or, I should say, as you’re getting to know your current self better. Maybe you lost your vibe during these long pandemic years, maybe you’ve had a baby and parenting has taken over *raises hand*, maybe you realized the role you’ve been playing doesn’t fit and you're finding the self that’s been long hidden.
For most of my life, getting dressed has been my comfort zone. If I’m bummed out, shy, scared, uncomfortable, I dress up more and feel instantly better. This little trick isn’t working at the moment, so I’m thinking a lot about why that is. As a new parent, I bristle against the idea that I’ve lost myself. “I WILL NOT LOSE MYSELF,” I shout into the ether and maybe this holding on, I’m sorry, I mean white knuckle grasping at an idea of my former self is causing all the trouble.
I have the new parent thing tripping me up, which calls for a lot of functionality, and then we have another aspect that’s being whispered among my friends: Age. And, shhhhh, relevance. The friends I’m whispering with and I are in our 40s, which I truly feel is young! As the great Aaliyah said, ‘age ain’t nothin’ but a number,’ and I believe that! Can you tell by the exclamation points how desperately I believe this?!?!
But I think there’s not much cultural context for our 40s. Growing up, I know my parents were in their 40’s at some point but I was much more focused on my pre-teen to teenage self, if you can imagine that. We hear so much about your 20’s, your 30’s maybe, but then what? It appears that 40’s is a time of pretty damn official adulthood, it’s a time of ‘mid life’ and responsibility, it’s a time of maybe needing to visit a podiatrist because now your ankles and arches hurt out of nowhere. It’s a time where you wish you started a retirement fund earlier, but also wonder if the Earth will just be a flaming orb by then and 401ks won’t matter so much? Anyway, back to clothes–
The topic of relevant style at this age is a curious one. Who are we trying to be relevant to or for? Do we really care if we’re ‘on trend,’ because this seems to be a dying concept in this time of anything-core. And trend and relevance has always been wildly subjective. I think we’re really talking about a strong sense of self. An interior world that we’re trying to convey to others through style. So in this decidedly adult time- where the weight of our current lives, futures, pasts, families, careers, etc feel so heavy, it’s easy for the self to get buried.
I see how the functionality takes over– The leggings and the sneakers. And listen, been there, nothing wrong with that, but it really doesn’t make me feel great. I feel functional without the ‘fun.’ Adulting is already often boring, so it’s nice to at least have something interesting to look at. Yet even as I acknowledge all this, I haven’t figured out a satisfying way to express my inner self these days. The good news is ‘nothing lasts for long,’ including this weird time of not knowing ourselves. So we dig into the process, and start to excavate a new self.
Here’s where we start: “What’s most important right now?” followed closely by “How do I want to feel?”
Although typically not a high fashion priority, I realized in my day to day it’s most important that I'm comfortable above all else. As for how I want to feel: interesting, classic, functional, attractive (to myself at least), fun, casually luxurious, nonchalant yet put together, unique – But to narrow it down, if I just focus on ‘comfortable’ and ‘casually luxurious,’ it lifts my mood and I can feel that inner self strut around with her little chest puffed out.
I have observed a few things that work for this comfortable/casually luxe combo that I’d love to share in the hopes they help your little inner self strut around too:
Ankle bracelets- These make me feel surprisingly amazing. Like, disproportionately amazing. I’ve been wearing a small pearl one that Jessica Winzelberg made for my wedding, and lately I almost never take it off. Sleep with one on and wake up feeling somehow sexy. Keep it on over your slouchy tube socks and sneakers and feel like you understand something about life that no one else does. Roll it out from under your leggings as you slip on your Birks and feel like a tantric Goddess. Jessica doesn’t typically make them (but she has many other wonderful pieces to light you up,) but Beatrice Valenzuela has some beautiful anklet options right now.
Familiar shoe styles with a luxe spin- Actually forget the Birks mentioned above and get yourself a supple and luxurious take on a classic shoe style. It just so happens that my friend and studiomate Jamie Haller is the ultimate purveyor of these currently, so this has worked out well for me. The nice thing here is you’re incorporating something into your day to day that you don’t have to ‘figure out.’ A classic loafer, ballet flat, or sandal is easy to slip into, literally and figuratively. But because the materials are outstanding and the proportions interesting, it makes me feel more chic and luxurious than when I’m wearing the standard faire.
A very crisp and classic men’s fit buttondown, preferably vintage- To be honest, I’m torn on this recommendation because oversized buttondowns also feel like a style crutch for me at the moment, but I can’t deny the casual yet put together ease I feel in my Turnbull and Asser vintage stripe buttondown procured from Mothfood Vintage. A quick etsy search shows a few options available (hurry, before I buy them) or you can treat yourself to a newly made one straight from London. The shirt I have feels miles better than my other often worn J.Crew options, again here due to the materials, the slightly more interesting proportions, the quality, and the brand esteem. I imagine a vintage option from Brooks Brothers or Ralph Lauren would scratch this itch as well. The 80’s businessman crispness makes you feel instantly put together and classic, and like everything else, getting it vintage has the effect of making it all the more personal and curated.
Last but not least, Denim- Duh, right? But specifically *slouchy denim* because it’s comfy, wonderfully nonchalant, but mostly because slouchy is one of the more interesting ways to wear denim right now. It sits a little lower on the waist and lends itself to pooling at the ankles for a proportion that feels simultaneously 90s nostalgic and refreshing. Vintage 501s with a waist measurement that’s 1-2” bigger than your own are always a great choice. Check out my tips for buying vintage denim online if you need some extra inspiration. I’d also be remiss if I didn’t mention my own Bliss And Mischief Denim is 30% off this weekend and a great slouchy choice when you go up 2 sizes from your usual.
Since I’m starting from the ground up, I like that these are all approachable and easy to incorporate even in my very functional day to day. I can also imagine them styled so many different ways for different personalities, vibes, ages, and body types. But the differing proportions and unexpected details keep them from feeling basic, a dreaded term in my style world.
I’m curious what’s giving you a sartorial boost these days? Or are you as lost as I am? Either way, comment below and let’s figure it out together.
xo-Hillary