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This week, I share four questions I get asked a lot. Unfortunately, they have no answer–or at least, no answer I can give you. From “Can I wear that?” to “Will this be in style next year?”, I’ll tell you what the questions are, why I can’t answer them, and how to find the answers for yourself.

Also, in Philosophy, I share a quote from designer Alexander Wang that pretty much sums up what Everyday Style is all about.

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Read the full transcript below:

Hello–and Welcome back!  You know, I like to think of myself as a knowledgeable person when it comes to style. I like to think that over the last 2 decades, I’ve learned a thing or two, and that I can answer most style questions that come my way, and if I don’t know, I at least know HOW to find the answer. But there are some questions I simply can’t answer, and even if I dressed women for a hundred years, I still wouldn’t be able to answer.  Today, I’m going to share four of them, and tell you WHY I can’t answer them.

But before we get to that, we’ve got a Philosophy segment, featuring one of my favorite quotes–and it actually reminded me of a client I worked with, so it’s a little bit philosophy, little bit Lessons from Linda, and it involves a question I got through email, so a little office hours as well. There’s a lot packed in there. 

Let’s get to it!

This quote comes from designer Alexander Wang who said 

“Anyone can get dressed up and glamorous, but it is how people dress in their days off that are the most intriguing.” 

To me, this is the very essence of style and a big part of why I called my business Everyday Style. It’s what you wear every day that truly defines your style. The challenge is, we still think of style as this thing we put on when there’s a reason to get all fancy, and obviously, lately, there haven’t been that many reasons to get fancy and glamorous.  But even when the world is normal, for most people 95% of life is lived in the everyday.  I remember a Linda I worked with early in my business, and we were shopping for a special event dress, but as we were talking, she was telling me how she was tired of feeling like a frumpy stay-at-home mom. She missed working and getting dressed every day, and she wished she could wear pretty things again. We knocked out the event dress really quickly and had a lot of time left, so I said, let’s shop for some everyday stuff. We got her some better jeans, a few tops, and even a casual jacket to replace her sweatshirt hoodie.  About a month later, she sent me an email with a pic from the event, which I love getting, but her email was really about how much better she felt every day in better jeans and a cuter jacket. But her email also said this “I don’t know why I thought getting dressed was so difficult before”

I’ve said a lot on this show that when people say,  they struggle to get dressed, they don’t really mean “Get dressed”–they are perfectly capable of putting on clothes.  They mean they struggle to get dressed in a way that makes them feel great. 

So let’s talk about why getting dressed in a way that made Linda feel great was difficult. 

I’m going to change the quote a little bit, with apologies to Mr. Wang and say that 

“Anyone can get dressed up and glamorous, but it is how people dress in their days off that is the most challenging”

There are 3 reasons for this–3 reasons everyday style is actually really hard. 

  1. The importance we place on it. If you don’t value style in your everyday life–the life that goes to the park and the grocery store, you won’t prioritize it. You won’t buy clothes you love for it. And then you’ll wonder why you never look cute for it. I know I’m a broken record on this one, but you have to buy clothes you love the way you really live. Plain and simple. You’ll always struggle until you embrace this.
  2. The second reason is that as you move up the dressiness, or formality, ladder, the expectations are much more clearly defined. Women who have to wear suits to work rarely struggle. There are very clear guidelines to follow.  Business casual is much tougher.  Casual Friday is the worst of all. As expectations are relaxed, and we have more options, it gets more overwhelming, and tougher to put together a look you love.
  3. Finally, as you move up that dressiness ladder, more, and better, help is available to you. Every single time I shopped  for a special occasion outfit with a client, there were salespeople bringing other options–often, really good options. I wasn’t nearly as needed as I was in the casual sections. Often, in those areas we wouldn’t see a single salesperson in the fitting rooms–you’re really on your own. This is when you have to rely on your personal style, and your knowledge of dressing yourself. Which is a skill that most women need to learn–and that goes back to the importance you place on it. It all starts there.

So, if you thought it was actually more difficult to look stylish on your quote “days off”, you weren’t wrong–and that’s why.

I told you that this quote also brought in an office hours component, and I’ve gotten a couple of emails from listeners who are starting the search for the perfect wedding dress, and aren’t sure what to look for. Here’s my advice to you ladies. For a lot of women, their wedding dress is the dressiest, most glamorous thing they’ll ever wear, which means that the people in the stores are actually really, really good at helping you. I know there are exceptions, but for the most part, those ladies, and men, know what they’re doing. Go into it with an open mind, and let them make suggestions. Bring your personal style into it, of course, but let them suggest styles. Wedding dresses are so different from what we wear in real life, that you might be really surprised. Let the pros help, and spend your energies finding great honeymoon clothes, or a great bridal shower outfit–those things will need more effort from you.  

When we come back, I’m going to share four questions that I simply cannot answer.

Let’s chat about unanswerable questions, shall we?  Unfortunately, if I were putting together a list of the top 10 questions I get asked, these would all be on it. In fact, they’d all be pretty close to the top, which means that women are frequently asking questions there are no answers to. Today, I’m going to share the four unanswerable questions I hear most often, tell you WHY I can’t answer them, and HOW to find the answers for yourself. 

The first question I can’t answer is “Is fill in the blank worth it”. I’ve heard: Are Hunter boots worth it?  Is it worth it to get these pants altered?  Is premium denim worth the money? And probably a hundred more Is it worth it questions.  And I could answer all of these questions…for myself.  But I can’t answer those questions for anyone else. When people ask this question, they think they’re asking about price, but they’re not…they’re asking about value. And value is highly personal. I’ve talked about this before, but in case you haven’t heard it, price and value are not the same thing–in fact they have very little to do with each other. Price is a relationship between the boots or jeans and the store, or the pants and the tailor. It’s an objective number that has very little to do with you. Value is the relationship between the item and YOU, or the pants and YOU.  It has very little to do with the price. Let’s take Hunter boots for example, and lets say for easy math they cost $100.  If they’re your style, and you live in a climate where you need rainboots, and they would make every outfit you own feel so fabulous, they are probably worth it–to you.  On the other hand, if you live in the desert, and can’t stand the way tall boots look on you, a $100 investment probably wouldn’t be worth it…to you.  Same price, same boots, but the relationship–the value–is different.  Every single time you want to ask “is it worth it” about ANY purchase, you have to add the words “to me, right now” to the question. So how you decide if something is worth it to you, right now? 

Ask yourself first and foremost–can I afford it? If you can’t afford it, and you don’t really need it, the answer to is it worth it to me right now is simply no. Put it back.

Second, ask yourself, do I love it? Clothes you are ambivalent about, regardless of price, are never worth it. Pants you wouldn’t wear, even if they were hemmed to the right length, aren’t worth getting tailored. 

Finally, ask yourself how long, how often would I wear this? A big part of value, or worth, comes from utility. $100 leggings you wear 2-3 times a week are a better value than $50 jeans you wear once a month.  

Focus on building a wardrobe based on value, not just on price–and a valuable wardrobe is one filled with clothes you love and actually wear. 

The second question I can’t answer is “Can I wear (fill in the blank)?” Variations on this question are things like?  Can a pear wear skinny jeans?   Am I too old to wear distressed jeans? Can I wear yellow?  Here’s why I can’t answer that one. Because you’re not really asking if you CAN wear something. It’s just like people who tell me they don’t have time to get dressed. They’re never naked. They’re saying they don’t have time to get dressed a way that makes them feel good, just like we talked about earlier.  When you ask, Can I wear that, the simple answer is yes, of course. If you can put it on your body, you CAN wear that. So that’s not what the question is about. The question is really asking “will I like the way I look and feel in that” and that one, no one but you can answer.

Let’s take turtlenecks, for example, can I wear turtlenecks? Yes, I am able to put one on my body, so I can wear turtlenecks.  Will I like how I look and feel in a turtleneck? No, not one time. Not ever, not under any circumstances. 

So can a pear wear skinny jeans? Sure, lots of pears do, I’ve seen it with my eyes, so I know it’s possible. Will you, as a pear, like the way you look and feel in skinny jeans? That I can’t tell you. 

Same with a woman in her 60’s in distressed jeans. You absolutely can put them on your body, again, I’ve seen it with my eyes–I”ve actually facilitated that happening. Will you feel like a bad mamajama, or a fraud who’s trying too hard? That’s the part only you can answer, because both of those are valid responses  

So how do you find that answer?  Easy, you put it on your body and ask yourself, do I like this on me.  If you want to shorten that process, you learn the principles of dressing yourself–like your Signature Style, Your best colors, your body shape. Those things make it easier to know, before you put it on your body if you’re likely to feel good in it. 

Over the years, I have to say I’m surprised by the number of women I’ve encountered who don’t want to try things, and don’t want to learn the skills…it’s kind of like they’re waiting for this inherent knowing to come down on them, and if that’s you, stop waiting–it isn’t going to happen. 

I think this happens because a lot of women believe that style should be in our female DNA, and therefore it isn’t a skill we have to learn, but it is–it’s something you develop by learning the principles and then practicing

The third unanswerable question is Where can I find (fill in the blank). Now this one is kind of a trick question, because there are some questions I absolutely can answer, like where can I find Rothy’s or where can I find Elmoi bras. Objective questions like that I can absolutely answer, but that’s not what I’m talking about. 

I’m talking about the subjective “where can I find” questions. The three big ones I get are “where can I find good jeans” “where can I find comfortable shoes” and “where can I find clothes for my body shape?”.

 Let’s talk about jeans first. This question gets asked a lot usually in the fall, and people always have lots of recommendations, which is great, but they’re giving recommendations based on what works for THEM. Someone will ask what brand of jeans they should buy, and someone else will say, NYDJ is amazing, and they’re 100% right–NYDJ are amazing jeans…for some bodies. For others, they’re terrible. Finding the best jeans for you means finding jeans that are great for your body, butt, and budget, and within those three things, there are thousands of options.  Some people swear by Old Navy Jeans–to me, they’re a denim dumpster fire. 

So, You can take recommendations from people all day long, as long as you realize they’re telling you what works for them, and nothing beyond that. If you want to use that as a starting point, fantastic, but realize you’re going to have to put in a lot more work to find jeans that are great–for you. I recommend going to a place that sells a lot of different brands and styles so you can compare more easily. 

Where can I find comfortable shoes is kind of the same as jeans, but kind of not. The difference is there are comfort shoes, and then there are comfortable shoes. Comfort shoes is an objective category. These are shoes that were designed with comfort, and proper foot alignment in mind. These are brands like Dansko, Birkenstock, Abeo, Vionic, Taryn Rose. It’s a technical category. 

Comfortable shoes, on the other hand, is a subjective category that simply means, what shoes will feel good on my feet? No one can answer that one for you.  I remember years ago, someone in my Facebook group asked where she could find comfortable work flats, and a few ladies were raving about the Katie and Kelly brand from DSW.  I actually needed a new pair of dressier flats so I gave them a try. They hurt my feet so bad that I have never even tried another pair of Katie & Kellys on.  They were miserable. 

Comfortable shoes are about finding shoes that by chance work with your foot shape, your arch, the way you walk and stand and all that good stuff. Nobody can answer that but you.  So, if you want to find technical COMFORT shoes, that is something you can google. If you want to find comfortable shoes, you need to put them on your feet, and start looking for brands that consistently work for you. 

The third “where can I find” question is “Where can I find clothes for my body shape” and honestly you guys, I get this one a ton. How easy would it be if there was an hourglass store, or a pear store, or an apple store–I guess that one does exist, but they don’t sell jeans that fit my body well. Unfortunately, it doesn’t work like that. Almost every store sells clothes for every body shape, you just gotta know how to find the individual pieces. You may find some stores whose tops are cut better for your narrow shoulders, or brands that tend to do a lot of your favorite neckline, but there isn’t a list of stores that specifically sell to certain body shapes. This again comes back to trial and error and learning what works for you. You gotta do the work!

My last unanswerable question is “Will (fill in the blank) still be in style next year”. I also get will (fill in the blank) come back in style?  For real, if I could see the future, I would see myself right into a giant lottery win, and a house on a beach. I would not be using that power to tell you if raw hem jeans will be a thing in 2022. I simply don’t know! I get this question a lot around Capsule Guide time, and women are hesitant to buy something because they’re afraid they’ll look so last year, next year! Here’s what I say to them, and what I’ll tell you, too. Never buy anything because it’s in style right now…buy it because you love it, and will want to wear it next year.  Also, it goes back to the difference between trends and fads. If you’re still concerned about buying things because they’ll be out next year, I really encourage you to listen to my episodes the truth about trends, and are skinny jeans still in style. Both of those will hopefully put this idea of “you’re either in, or you’re out” to rest.  

For the question will (fill in the blank come back in style), my answer is probably, but do you want to hang on to those things just in case,and will you want to wear them if they do?  If fashion trends repeat every 25 years or so, do you really want to lug all that stuff around for 2-3 decades, and will you be the same person with the same style then? 

I got a half-joking email last summer, from one of the first clients I worked with when I started my business in 2012, so you know–8 years later.  We had decimated her shoe collection in a memorable way, and a pair I admittedly encouraged her to get rid of were those black platform steve madden slides we were all wearing in like 1995.  They were in rough shape, and in 2012, they did not look current. Because they were almost 20 years old. She never wore them, and they weren’t her style. 

This Linda had a hard time parting with anything, so I’m sure she remembered every piece we got rid of. Anyway, this summer she emailed me with the subject line “remember those shoes you wouldn’t let me keep?” and a link to Steve Madden’s rerelease of those iconic slides. I know you know the ones I’m talking about. I’ll link to them in the shownotes. 

She said, turns out I should have kept them with a winky face, which is I how I knew she was kidding–at least partially. Let me say, it is rare that an item comes back in the exact same way–usually its a trend re-interpreted, which just makes the things you’ve been hanging onto look even more dated, like so close but not quite.

But these did, admittedly. But they looked silly on her in 2012 because she wasn’t an 19 year old girl in trendy shoes. She was a thirty something stay at home mom in dated, shabby shoes, so we let them go.  Last year, she would have been a 40 something stay at home mom in trendy, shabby shoes. Time didn’t make those shoes any better for her. If you’ve got super high end, designer things you can still wear, hang on to them. Anything you bought at macy’s, you can let go of confidently. It is highly unlikely they’ll stand the test of time, or that you’ll be the same person if and when they come back around. 

That’s all I’ve got for you today. Your homework is to think about your Everyday Style–is it as fabulous as you’d like it to be? If not, what’s one little change you can make to make how you look on your days off, more intriguing, as Alexander Wang would say.  

We’ll be back next week with an episode on finding your best colors–it’s an episode you won’t want to miss. Head over to our website to get a sneak peek at what our Guest Expert will be talking out.  It’s gonna be a good one!

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