How to Make Getting Dressed Easier - Part 1
The first of a series with my tips on how to make getting dressed every day easier and more fun. My first tip? Make time to try things in your closet on and create an outfit roster.
Today’s Newsletter is the first in a series that will seek to provide some answers to the question of “How can I make it easier to get dressed every day?”. It seems that this is something that many of us are struggling with — what to wear to feel good, how to find things that make sense to use, and how to define and then stay consistent to our personal style. While there is no simple answer or checklist for this, there are so many things that you can do to make it easier. So, this series will include tips, ideas, and suggestions for how you can make it easier for yourself. Think of this as an ongoing and evolving list of recommendations that will help you define your style, streamline your shopping (eg: shop with intent and not buy, buy, buy), get dressed, and feel like the best version of yourself. Let’s get into it!
If you have been here awhile, you know that I am passionate about the power of clothes and great outfits to make us feel like our best selves. A great outfit - one that gives you a full body yes - can shift your mood, give you the confidence you need to make a great presentation or pitch at work and make you feel however it is you need to feel on a given day. It can also make you feel comfortable and good enough to focus on the things that matter on any given day. Since you are here, reading this newsletter, I think you probably agree (or are at least curious)!
In all the places where I consume content (on Substack, on Instagram, on TikTok), I see a lot of discussion about how people, (mostly women,) don’t know what to wear anymore. Of course, the algorithm is at play here. I share content related to personal style, outfit inspiration, and getting dressed every day, and the algorithm (at least on Instagram & TikTok) is surrounding me with similar content. You might argue that I’m in a bit of an echo chamber, and you wouldn’t be wrong. But the conversations I’m having with real people in comments and my DMs, plus texts and conversations with my IRL friends make me pretty confident that this is something that women - especially women in their 30s and 40s (although of course not exclusively) are struggling with.
There are many reasons for this — the marketing that we are constantly inundated with - and not just ads in the traditional sense, but organic, user-generated content - about the latest thing or piece or item that is “it.” The comparison game of social media - we see people who look “perfect” every day, even though “perfect,” is a construct! Although life has gone back to “normal” post-pandemic, we have a lot of processing to do coming out of a nearly 2-year-long pandemic during which we all spent various amounts of time homebound in an unprecedented way, and experienced changes to all aspects of our lives - including when we leave our homes and what for, how we gather and who we gather with, and how work works. To name just a few.
Regardless of the root causes of this - the challenge is simple - it can be hard to figure out that personal style sweet spot — the intersection of what you love, what you’re going to wear, and what you feel great in. And then, of course, even when you do have it figured out, there is still the work of putting together the pieces - finding the right combinations of things that you own, put together just so in a way that sings.
But it doesn’t have to be! Most days, when I am getting dressed, I follow a series of outfit recipes that I know work for me, and that I love. It’s not necessarily a uniform - I don’t wear the same thing every day, but I have some formulas that I follow to make getting dressed fun and simple and to make sure I don’t overcomplicate things.
The reality is, that most people with the best style are following an outfit receipt or uniform of sorts. I was recently listening to a podcast by
featuring Eleanor Leftwich. Eleanor is notorious for her incredible eye for style, and for embracing a uniform - and I love when she talked about how important (life-changing!) it is to find a uniform and stick to it - when you love something, buy it in every color. It’s not boring. It’s consistent. And, it makes everything easier. We could all use a little less friction in our lives.
There are so many things that you can do to make this easier, so I wanted to start a series where I share tips, ideas, and suggestions for how you can make it easier for yourself. Think of this as an ongoing and evolving list of recommendations that will help you define your personal style, streamline your shopping (eg: shop with intent and not buy, buy, buy), get dressed, and feel like the best version of yourself.
So, how do you even figure out your formula or the recipe that you are going to follow? Well I’m going to be honest with you - if you are struggling with getting dressed every day, and feeling great about the clothes that you have, then you are probably not ready to jump right into a uniform. There are a few steps that you have to take before you get there. But don’t fret, because today’s tip is for you. I think you should start by making time to try the clothes that you have on.
Do a Little Try On At Home
We all need ideas to be able to get dressed. You might find those ideas and inspiration on Instagram, in print magazines, on TV, in movies, on Pinterest, in real life, on Substack - really, anywhere. Ideas and inspiration are abundant. If you are open and looking - you will find them everywhere (PS, can you tell I’m reading this right now).
The execution of the ideas, well, that takes a little work. Anyone who has pictured an outfit in their head for weeks - picked and prodded at it, imagined how great it will be to slip on, and then, 10 minutes before they have to be out the door has gone to put that highly anticipated outfit on only to find out it absolutely does not work and does not feel great — gets it. Because (my inner consultant is showing here) - it pays to plan, because, when you have a plan - execution is much easier.
Every few weeks or so I will spend a weekend nap time trying some things on and coming up with new outfits, and that helps keep me inspired and full of ideas of how and what to wear.
I take pictures on my phone and keep them in an album called “WEAR ME.” When I buy something new, I ALWAYS DO THIS - I try the piece on with a few things I already own - to confirm that I’m keeping it, that it can be worn with things I already have, and to have some ideas stored away about how to wear it so it doesn’t sit in my closet unworn.
You can do this too! The key is that you’re doing it at a time when you don’t need to rush out the door. You don’t need a ton of time, but you do need to remove the pressure of needing to be ready to go in X minutes.
Take 20-30 minutes and pull a few things out of your closet that you love. Pop in your headphones and turn on your audiobook, podcast, or favorite playlist. (Maybe pour yourself a glass of wine?) Use some of the formulas here or here (or refer to saved or screen-shotted images on your phone), and recreate looks or styles that you like. Start simple - grab your favorite jeans and a white tee. Can you add a belt? Add an oversized shirt, or steal one from your partner if you don’t have one. Find a flat shoe - like a loafer or a ballet flat? How’s it looking now?
Maybe you need more ideas for work and you grab a skirt, and a button-down shirt. Can you layer in a cardigan or a sweater over your shoulders? Try out a blazer? Add an interesting earring or necklace? Put on a tall boot?
Make this a practice. Something that you do regularly. You will start to build up an arsenal of outfits that you know you can reach for when you don’t know what to wear, when you’re running low on time, when you’re packing for a trip, or when you just want to feel great but not think about it too much.
When you implement a practice like this, you will start, over time, to figure out what your closet “without fails” are (this is a term coined by Tibi founder, Amy Smilovic). Per Smilovic (who has a WEALTH of knowledge on getting dressed, personal style, and building a closet that you love and is a unique reflection of you as an individual), your Without Fails are the items in your closet that function as basics, although they don’t need to be basic at all. They are the pieces that go from season to season, and that you wear a lot. You’ll start to realize what you love and reach for all the time, and you’ll start to see what doesn’t work - whether it’s because it doesn’t fit, needs to be replaced, or just doesn’t suit you. This is an important step towards being inspired and excited by your closet, and having a wardrobe of things you love.
As you try things on, take pictures. Save them in your own album. Can you come up with 5 or 6 ideas? Now you have 5 or 6 outfits you can put on and feel great about the next time you’re getting dressed. Most of us don’t have that much time to think about or play around with what we’re wearing every day. You know that opening scene in the Devil Wears Prada, where there is a montage of models/fashion girls getting ready for the day? Yeah, no, that’s not real. We need (and want!) to get ready quickly so we can go about our day. So, to do that, and also wear something that makes us feel great, means you go into the act of getting ready with an idea in mind. Maybe you tinker with your shoes, or your earrings, or a different accessory. But, you have something in mind (and ideally you’ve put that something on your body before so you can be pretty confident that it’s going to work the way you want it to!)
If this feels like an impossible thing to do or something that you want help with, then I would love to hear from you. Shopping your closet to show you how much you already have (and yes, of course, we will find some gaps) is one of the key services I’d love to work with clients on. You can always leave a comment, join the chat, or send me an e-mail & we can discuss your specific questions and see if there might be an opportunity to work together.
In my own recent try-ons, I have come up with several outfits that I have gone on to wear regularly - and in many different permutations. Here are a few of my favorites:
Here is something I wear when I want to wear sweats, or I’m going to (eventually) workout, but I also need to leave my house. Frequently on the weekends, I’ll wear this until I get fully dressed for the day. I’m wearing leggings and a sweatshirt, but I add the socks and the oversized jacket, with the sleeves of my sweatshirt showing to make it just a little more intentional, include some layers, and feel a little put together. More on the why of this outfit & tips for making athleisure feel a little more elevated here.
In the spirit of showing how I repeat and re-wear pieces in my closet - here is the same oversized denim shirt styled over a black hoodie, which is layered on top of my favorite ribbed t-shirt. I’m wearing wide-leg black jeans. My daughter was sleeping outside the door of my bathroom, so I didn’t want to clonk around in shoes, but I would wear this with a boot, sneakers, or clogs.
This is sort of basic and boring, but you know what, I think that’s okay. Not every outfit is perfect. Sometimes you just need to put clothes on your body that feel good and are simple. I will call the bow my accessory of choice right now because even though I was just wearing jeans and a tee, I felt festive! This is the same ribbed shirt I used as a layering piece in the picture above, worn on its own. Looking at the outfit now, I wish I had put on a belt (A new, interesting, beautiful & functional belt is on my wishlist for 2024)- but I still wear this a lot, and I know it’s a great base to which I could add a cardigan buttoned up, an open cardigan, or a blazer.
Here is another riff on my winter uniform. I know that a lot of people might say this is boring too. That’s okay! I got this sweater from Reformation during their Black Friday sale, and I would pay full price for it again. The cut is amazing, and their cashmere is great (I have this cardigan and it’s another favorite). When I got it, I wore this sweater for 5 days straight. It will be in my weekly rotation this winter. Paired here with the Reformation Cynthia Jean (one of my favorite jeans right now. Note that the pair I have has no stretch, but they also have a stretch version of the style if you prefer a little give in your jeans. I’m on a jean hiatus right now, but am eager to try out their stretch version soon!) I’ve been really into the look of a navy top with a slightly lighter denim wash. It was above 40 degrees, so I exposed my ankles and wore flats, but could have just as easily worn socks and loafers, or a boot. The scrunchy was both festive and hid the fact that the next day was hair wash day. I added interest to this outfit with a long coat and scarf when I left the house.
I typically shy away from statement sweaters - since I wear them constantly I look for something less recognizable. But, I got this sweater last winter (unfortunately it’s no longer available, and the version from this year is not quite as good, IMO, but several other options here), and a matching one for my daughter (truly the sweetest thing), and I wore it a lot. (Tip that if you are pregnant, as I was last winter - cardigans are a great thing to focus on. Just unbutton as your pregnancy progresses. They also make a great postpartum uniform. More tips on getting dressed during pregnancy & postpartum here!) However, this is a great sweater. Really leaning into my inner Scandinavian here - especially with the socks + clogs. So ugly it’s good I guess?
I hope this helps to get your creative juices flowing, and gives you a gentle reminder to get into your closet and try some things on. YOU DON’T NEED TO THROW EVERYTHING AWAY AND START FROM SCRATCH. YOU NEED IDEAS AND TO PRACTICE EXECUTING THEM. Remember that this is supposed to be fun! The rules are - there are no rules. Wear what you love and what makes you feel great.
And, if you’re thinking about wanting some help, reach out (or check out some of the consults available right now.)
ICYMI:
My guest column on
- “Getting Dressed Makes Me A Better Mom”Holiday Gift Guides (If you’re a last minuter like me, there is still time for a lot of these gifts!)
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So many great ideas! And I have the same book on my nightstand.