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Tips for Finding an Authentic Outfit Each Day
NEWSLETTER
12/18/20254 min read
This is it, we’re in the holidays. I know you’ve heard it from so many other places so many other times – it’s both a magical lovely time AND an overwhelming time packed with all sorts of responsibilities and expectations. But what about your clothing?
Personally, I find that clothing follows the same chaos as the rest of this holiday time. There are events that require something specific – my personal nightmare of this is my kid’s spirit week at school where he’s dressing each day according to a different holiday theme. There are family dinners and fancy events where I want to show up looking my best. There are typical work days where I put together a casual, but collected outfit. Then there are days – MANY DAYS -- where I’m feeling cold and exhausted, and my sweatpants and sports bra are practically climbing out my drawers on their own and flinging themselves onto my body.
I wish all of these clothing needs were nicely lined up in my brain, politely taking turns, knowing when I was going to wear what outfit. But they’re not. This past week, the thoughts about what to wear were swirling into a mini tornado in my mind. I usually dismiss these thoughts, telling myself “I don’t have time for this”, before throwing on my sweatpants because they feel comforting.
If I was hearing a friend describe this as a problem I think my response would be “and?” or “okay, so what?”, because when I zoom out, I don’t actually hear a problem.
My definition of style is “an authentic external expression of how you see your inner self that day”. That means that the clothing you put on your body should “feel right” for you that day. There’s a feeling of self actualization. Your outfit is matching the “vibe” you're experiencing inside your body.
So if a piece of clothing feels comforting, that’s a pretty clear statement that the piece of clothing feels aligned with your needs and expression. I want to be clear that there’s a difference between clothing feeling comforting and comfortable. Your sweatpants feel soft on your skin 100% of the time, but there are days where they make you feel schlubby and unattractive. On those days, your sweatpants are comfortable, but not comforting. If you’re feeling schlubby in your clothes, then your clothes aren’t representing who you want to be and you’re not finding your style. If you’re wearing sweatpants and you think “uhh, it feels so good to just be comfortable and not worry about getting dressed up today” then you’re matching your inside self and outside self, and you are finding your style.
The permission I want to give to women over this holiday is to show up in your authentic style each day. If you have a day, or even weeks, where that means sweatpants and messy hair, then do that. If you have outfits planned that you’re excited about, then strut around in those without feeling apologetic. The big idea here is: If you can look at how you’re dressed, and say to yourself “yes, this is what feels good for me today” then you’re doing it right.
In case you’re feeling like you want extra support, here are some of my style tips I turn to when I’m having a hard time executing my style:
If you have a piece of clothing you know you want to wear soon, take some time beforehand to figure out the whole look. Pick a time you’re not rushed and plan your jewelry, what you’re going to wear with it, the shoes and maybe even how you’re going to do your hair. That way when you’re ready to whip it out, it’s low effort to put on and you know you’re going to feel amazing in the look.
Find some go-to favorite looks in your closet. I have a handful of dresses in my closet that I have a known way to wear them when it’s cold. I know what tights, shoes, and sweater to grab. When I’m feeling worn out, but also the desire to look put together, I turn to these outfits. I don’t have to spend any brain energy trying to create a look and I feel confident that I’m going to look good. You don’t have to reinvent the wheel every time. This is especially great for family events that you’re feeling rushed to get ready for.
If I’m feeling unattractive sometimes it’s just doing my hair and make up that makes me feel better. I keep my sweats on, but spend 15-20 minutes on my hair and face. Almost 100% of the time, this is a game changer for me. It gets me feeling confident and can change the direction of my day.
If you’re feeling stuck in a rut with your look changing even a small detail can be impactful. Try something that’s not usually in your repertoire. If you always wear low cut socks, try wearing crew socks exposed. If you always wear your hair down, try doing them in cute space buns. You don’t have to change the whole outfit, just find one thing.
If you’re worried about your outfit being “right”, think about how your body feels in it, not what other people will think about. Style is about how you see yourself. Does your outside go with how you feel inside? Do you feel like it makes sense when you see yourself? If yes, then you’re dressed right.
