I Figured Out Why Getting Dressed Is So Hard
It’s our last podcast episode before we go on a little hiatus, and I sat down on the mic solo to talk about a major life event. I had a realization this week: I’ve just come out on the other side of one of my biggest fashion growth spurts yet. We’ve all been through them and it’s kind of an amazing feeling when you hit a stride. And here’s what’s interesting: it wasn’t because of the new shoes I bought or the pile of clothes I got rid of, but because of how I shifted my mindset. Which means you can do it too.
It all started after I posted this video with Gabs Gofis a couple weeks back…
Earlier this month, she came on the podcast to talk about her series “In Between Outfits,” which are basically the looks that carry you through everyday life. Not the fancy events, or special occasions, but the looks you’re wearing to run errands, go to school pick up, see a movie, etc. (p.s. I have to say, this was one of my all time favorite episodes, so go listen if you haven’t. Consider it your required summer reading).
That conversation with Gabs made me realize something: I don’t really have many in-between outfits. I’ve always called myself a serial overdresser — I love a heel, I know how to get dressed for an event or a shoot. But my every day life felt more disconnected from my true fashion self. I just didn’t know how to bring down to every day life.
So I decided to ask Gabs to come over as a second set of eyes. I wanted the serial overdresser to meet the queen of everyday style and help me see what I wasn’t seeing myself, make a list, and figure out what, if anything, I was missing, and how I could change up even some styling cues to just make getting dressed every day easier.
Turns out I was missing a ton of everyday pieces — how validating. Plus, I kept trying to mix my fancy and non fancy moments, like a clutch with my every day pant, which was leading all my outfits to skew way dressier than they need to. Apparently I have no chill.
We recorded it to share with you guys and I’ll be honest — I was nervous to post that video. It wasn’t the version of me I’ve worked so hard to become — the expert giving advice. It was the first time I showed up asking for help. Turns out I wasn’t alone in my experience and I got so many DMs after that video. One of my favorites was from a listener who told me she loved the honesty of it, that she’s an overdresser too and the episode helped. I wrote back that we’re all figuring it out together, that no one’s style is ever really complete. And I meant that more than I meant it as a cute reply.
All to say, I realized that my pursuit has been wrong all along. Here I was saying I want to be more stylish, or I don’t have this “look.” Meanwhile, I was actually just trying to spend less time thinking about what to wear every morning and still feel good in it. The first goal is about looking better. The second is about living better. Those are not the same project, and the second is something we all desperately crave. I don’t think the goal is a perfect wardrobe anymore. I think the goal is a wardrobe that gives you your mornings back.
Here are the mental shifts that have dramatically altered my mornings:
Personal style is self care.
I think we’ve been sold this idea that one day we’ll wake up, open the closet, love everything in it, never make a bad purchase again, and just know what to wear. I don’t think that’s how style actually works. I treat my personal style with the same seriousness I treat the gym, or eating well, or anything else I do to feel good day to day. Practically, that looks like a few habits: cleaning out my closet once a quarter, keeping a running list of what I actually need, keeping my closet clean at all times, and staying on top of dry cleaning and resoling instead of letting it pile up.
Fashion and prioritizing the way you look gets a bad rep. It’s like society has filed getting dressed under vanity, as if it’s optional, and it’s only for people who are “into those things.” I’m here to tell you that investing in your personal style will change your life. I know that sounds dramatic, but I truly believe it. Caring about how you show up in the world gets painted as something you do for other people, but it shouldn’t be. It should be for yourself. It’s part of the larger project of taking care of yourself.
Let bad outfits teach you something. I saw this interview where Law Roach was asked recently about his biggest red carpet misses, and I loved his answer: he said people with real personal style miss often, because they’re taking risks and won’t get it right every time.
It made me think about the days when I’m halfway out the door and realize I hate my outfit. Instead of spending the whole day stewing on it, or letting it ruin my day, I’ve started treating it as data. To the point where I will literally sometimes write down what I didn’t like about the outfit and why. Maybe it’s the way my top is falling on me, maybe it’s the mixing of textures, whatever it is, I make a note of it and let it be a learning moment instead of a spiral. Easier said than done, but it’s truly changed my life.
Invest in your Tuesdays. After Gabs came over, I swore that moving forward, I’d invest in the every day — easy pants, crew necks, tees, and cardigans that get major mileage in my closet. I’ve been the gal that always waits for the big ticket items to splurge — the dream bag, the dress for that friend’s weddings — and those get no where near as much wear.
Dress for you. Every time you get dressed, check in with yourself: is this for the eyes of the person you’re meeting, or for what actually makes you happy? The majority of my most stressful mornings trace back to dressing for someone else. This applies to shopping too. Before I buy something, I always try to look at the item and ask myself if it’s something I actually want and will wear, or if it’s something I’ve convinced myself I want because I saw someone else wear it and look amazing. If it isn’t serving me and my personal wardrobe, then it’s not right for me. And those pieces are the ones that pile up in your closet and never get worn.
Create your own archive. This can be as simple as, I keep a folder in my phone of outfits I love, and it’s genuinely changed my life. There’s no version of you remembering every outfit you’ve ever worn, especially at 7am. Let your phone do that work for you. Then when you do have one of those inevitable stressful morning getting dressed you can easily scroll through your outfit photo library and pick from there. You’re removing one more decision for tomorrow already.
Repeat outfits on purpose. Build five to ten Monday-through-Friday outfits you love and can reach for without thinking. They’ll become your secret weapon for speedy mornings.
Phone a friend. I say this all the time, but you have to practice your style. Invite a friend over, hand them your closet, spend an hour trying things on and getting a new point of view. Style is never finished, and maybe that’s because we’re never finished either. Our lives change, our bodies change, our jobs change, our taste changes, so why would our wardrobes ever be “done”? It takes ongoing attention, the same as anything else in your life you actually care about. If you want a guided version of this, Allison Bornstein, who is both a friend of mine and the show, offers styling sessions and she’s someone I LOVE for it.
Sending love to your future self in front of your closet tomorrow AM and hope this helps! <3
I love all of these. I’ve been in a similar boat where I’ve felt a bit disconnected from my everyday style. For me it was about embracing colour in my everyday pieces that has helped me love my looks more! Also I use this all called Indyx to help me keep track of what I wear and love - so good!
Love everything about this and all your mental shifts. We are all still figuring this out and evolving and that's the point!!! Fashion is fun.. and you and Gabs are living proof of that. xo