Getting Dressed When You Don’t Feel Like Yourself
There are seasons when getting dressed feels like a task you used to know how to do. You open your closet, look at clothes that once made sense, and feel nothing. Or worse—disconnected, uncertain, maybe even a little grief. The outfits you wore with ease in another chapter now feel unfamiliar, as if they belong to someone you can’t quite access anymore. You stand in front of the mirror hoping something clicks, and all you see is someone trying.
Styling isn’t just about how you look when you feel your best. It’s about how you show up when things feel blurry, tender, off-kilter. Not as a costume or a mask—but as a reflection of who you are right now, in this exact moment. There’s something grounding about getting dressed with honesty, even when you don’t feel ready to shine.
People rarely talk about how personal style becomes tangled in life’s shifts. Burnout. Loss. A breakup. A move. A career ending or starting. A body changing. A role expanding or vanishing. These aren’t small things. And yet we often expect our style to remain untouched—to keep functioning as if nothing else has moved. But when your internal landscape has shifted, your external choices do too. That doesn’t mean you’ve lost your sense of style. It means you’re in transition, and transitions are disorienting. They call for different clothes—not necessarily new ones, but ones that can hold the version of you still taking shape.
The first step isn’t about shopping or editing or finding inspiration. It’s simply noticing. Observing your emotional state before you get dressed, not after. Instead of asking, “What should I wear today?” try asking, “How do I want to feel a little more like myself?” The answer might be steadier. Softer. Sharper. Hidden. Seen. If you’re feeling fragile, choose a look that helps you feel grounded. If you’re foggy, wear something that offers structure. If you’re quiet, you don’t need to push for loud. Just something that feels intentional. Something that doesn’t betray your current state by pretending it’s something else.
There’s power in having one outfit that works no matter what. I call this an “anchor outfit”—a reliable go-to that holds you without demanding anything from you. It might be a soft tee and well-fitting trousers, a monochrome knit set, or a button-down you can layer and forget about. Whatever it is, it should feel like a quiet “yes.” Not because it’s impressive, but because it doesn’t fight you. It lets you show up. And on the days when nothing else does, that’s enough.
When everything feels unfamiliar, reach for texture instead of trend. Texture is forgiving. It doesn’t ask you to be bold or on-brand. It simply gives your body something to respond to. A smooth knit. A broken-in denim jacket. A heavier fabric that reminds you you’re here. It’s not about looking styled. It’s about feeling supported. Clothes that feel good against the skin often bypass the noise in your head.
The mirror can feel unforgiving in these seasons, but what if it became a check-in instead of a test? What if instead of scanning for flaws, you asked, “Does this feel like the kind of support I need right now?” Some days, just showing up to the mirror is the victory. You don’t have to fix your reflection. Just meet it with honesty.
One of the simplest ways to reconnect is to choose one piece each day that makes you feel seen. Not the full outfit. Not the most styled version of yourself. Just one thing. A pair of earrings you used to love. A jacket that feels like you. A color you haven’t worn in a while. One small shift is enough to remember there’s still a part of you who knows how to dress with feeling—even if it’s buried under fatigue or numbness or distraction. You don’t have to reach all the way back to the person you were. Just reach toward the person you are now.
Style grief is real. Sometimes you’re not just trying to get dressed—you’re grieving the version of yourself who used to love getting dressed. Maybe that version had more time, more energy, fewer responsibilities. Maybe you hadn’t gone through the thing you just went through. Maybe you hadn’t lost something, or someone. Maybe you wasn’t carrying the weight you’re carrying now. And it’s okay to miss that version of yourself. But don’t make the mistake of thinking you need to become her again to find your style. That version of you had their season. You’re in a new one now. And this season deserves clothes that fit it, not the ghost of a previous life.
Start with clothes that don’t ask questions. Not “Do I still fit this?” Not “What will people think if I wear this?” Choose pieces that don’t push against your nervous system. And when you’re ready, experiment—gently. Try something unexpected on a low-stakes day. Mix something soft with something bold. See how it feels to wear something that belongs to your next chapter, not your past.
There’s no deadline for getting your style back. There’s no perfect moment where it all clicks. What there is—is you, showing up one outfit at a time. Quietly saying: I might not know who I am right now, but I’m going to keep dressing like I care. Like I matter. Like I deserve to feel like myself again.
Because you do.
With all the style and love you deserve,
Monica