The Top 20 Obstacles to Great Style and How to Overcome Each One

Poplin Client Angela in action.

As a personal stylist for women based in Seattle, I’ve spent nearly a decade listening to women talk about their struggles with style. These are among the most common challenges I hear from women. What resonates with you?

Identifying your problem is only the first step. Rest assured, there are solutions. As a Poplin client, we take a deep dive into creating a strategy and providing tools to solve your problem on an ongoing basis. For now, here are some approaches you can take right now. Looking for even more perspective? Most also have a client testimonial that is applicable. Enjoy the resources available and as always, let me know how it goes. I always love to hear from you.

The Top 20 Obstacles to Great Style and How to Solve Each One

Poplin client Ashley.

Poplin client Amanda.

I’m tired of staring at my closet full of clothes and feeling like I have nothing to wear. Nothing inspires me. No matter how many new pieces I buy, I inevitably feel this way within a few months of shopping.

Solution

This is one of the most common statements I hear from women. Your closet should feel like a boutique curated just for you. Every piece should make you feel amazing. It should be comfortable, flattering for your figure, ideally limited to colors in your color palette, communicate your authentic personal style and whenever possible, reflect your values. Every piece also needs to fit and communicate to the world that you are as successful as you are. No more pilling sweaters that “still work.” If this isn’t the case, you just get frustrated and end up wearing the same 10 items repeatedly and everything else becomes noise. Edit your closet to eliminate anything that doesn’t meet this criteria so that every piece you pick up is going to give you a win.

Client Perspective: Ashley and Jenny and Amanda and Tammi and Nancy

Nothing feels like me. I feel too old for some of my pieces but I also feel way too young for others.

Solution

This comes up a lot for women in their 40’s and early 50’s. For some reason, as women reach this age, we get the message that we go from crop tops to drapey, oversized Eileen Fisher pieces. It’s simply not true. Remember, you’ve got another 50 years or so to go. Do you really want to be wearing the same style for the next half of your life? There is a middle ground, embracing items that make you feel sexy, powerful and like yourself without wearing items that feel like they were made for a much younger you. It’s also important to note, that styles often work for a very wide range of ages, so just because your 18 year old niece has the same pair of pants from Anthropologie that you do, does not mean you are wearing something inappropriate for your age.

Client Perspective: Kate

Poplin client Laura.

I used to have a great sense of style but as my body (or lifestyle) has shifted over the years, I have no clue what to wear. What used to work, doesn’t feel right anymore.

Solution

If this speaks to you, not to worry. You are not alone. Our bodies change over time, especially after having babies. It can be tough to learn how to dress a new body, especially if your negative self talk is telling you that your current body isn’t as good as the previous version. This body is keeping you alive, so it’s to be appreciated. I know it’s hard, but try to take a step back and determine your body shape without ever knowing your previous body shape. You may be surprised at how obvious your new silhouette is. Then, try the Poplin dressing for your body tools to help you on this journey. Also, it’s about the shape NOT the size. The strategies are the same weather you wear a size 2 or a size 22. All are good:)

Client Perspectives: Laura and I-Hua and Divya


I know what I think is cool, but I don’t feel like I can pull it off. And, even if I did, I have no idea where I’d wear those clothes. They are certainly not practical for my life.

Solution

I love this one! Honestly, gaining the confidence to break way out of your comfort zone is much easier with the endorsement of your very own personal stylist. After all, having an independent person tell you what works and what doesn’t feels measurably different than having a friend or family member without expertise weigh in. If you are tackling this one on your own, just remember that YOU decide what you can pull off. If you believe it, everyone else will, too. And as for functionality, that’s not as hard as it sounds. Check out the Poplin Pinterest Boards for ideas on pieces that communicate your authentic personal style, flatter your frame and are functional for your life.

Client Perspective: Taylor and Abby and Sara

Poplin client Lauren.

Poplin client Caitlyn.


My weight fluctuates and I feel like I waste money on clothes that don’t fit only a few months later. So, I just live in stretchy pants or the same jeans and hoodie.

Solution

I am the queen of weight fluctuation. Honestly, I see it as an asset when it comes to styling. I work with real women, so showing up as a size 2 with stilettos feels inaccessible to most women in my city. Over the years, countless women have shared that seeing how I embrace my personal style in functional clothing that also flatters my changing frame is really helpful and feels more approachable. And, I can tell you, I do not live in stretchy pants. The advice for this one is much more extensive. For now, a couple of key takeaways. Invest in pieces that you can wear as your weight changes. I’m a triangle, so I spend more on tops, jackets and dresses that can work for multiple sizes and less on pants that may or may not fit months later. Be kind to yourself and lean into the rules for dressing your body to give the illusion of natural balance. Also, only keep items that fit right now in your closet. Move other pieces to a different place in the house. Have a box of “too small” items on the top shelf in your kid’s room, for example. And another box of “too big” pieces on a shelf in the laundry room. When your weight changes, you’ll go find them and you’ll feel like you have new clothes. It’s just fine to keep this rotation going. It eliminates negative self talk when you are in your closet and helps you keep a functional capsule wardrobe. If you limit pieces to your color palette, everything will go with everything else.

Client Perspectives: Ellen and Caitlyn and Christina and Lauren

Poplin client Delight.

Poplin client Natasha.

I have so many items in my closet with tags on them because I’ve never worn them. I feel guilty about spending the money.

Solution

Budgets are real. Even folks with very high incomes don’t like to waste money. And guilt is a very powerful emotion that can have a substantial impact on decision making. So, let’s start by eliminating guilt. If that piece isn’t right for you- it needs to go. Remember, it should flatter your shape, communicate your authentic personal style, be in your color palette, align with your values when possible and be at the level that you are at. It also needs to fit. If any of these criteria are not met, it’s time to sell it, give it away, return it donate it, whatever. Get it out of your life. If it DOES meet your criteria and you haven’t worn it because you, “have nowhere to wear it.” It’s time to take action. Find a place to wear it and go within the next month. That’s what the internet is for.

Client Perspective: Natasha and Delight

I have no idea how to dress my body or what colors to wear. I hate shopping because it feels like nothing works for me. I’m at a total loss. I’ve watched YouTube videos and still don’t get it.

Solution

My Dear, Poplin is all over this. Each client gets a password protected webpage that shows her what pieces are flattering, what items aren’t, her ideal color palette, a list of recommended retailers based on her budget and personal style, and a collection of outfit photos made using new and existing pieces in her collection so getting ready each morning is effortless.

Client Perspective: Aparna and Ellen and Connie

I struggle with taste. I really don’t have a sense of what looks good or doesn’t. I feel like I’m not creative and just want someone to tell me what to do. Often I buy the exact outfit on display so I don’t have to figure out how to put an outfit together.

Solution

Everyone has their own taste and it’s vital that when you are communicating your authentic personal style, you feel incredible. What may feel amazing to one woman will decidedly not have the same impact on another. This is why the consultation process is so important. Whether you are working with Poplin or diving into your own style evolution, be honest with what you want to communicate and what you truly like. Often, clients feel sheepish admitting that they like things that feel quirky or dated. But, those are what make your authentic personal style all yours and help differentiate you from the crowd. There’s always a way to integrate those details into current pieces.

Client Perspective: Natalie

Poplin client Lauren.

Poplin client Jess.

It feels like it’s never the right time to make my style a priority. When it comes to balancing the needs for the family with my own needs, feeling good about my clothes seems like a “nice to have” rather than a must have.

solution

Understood. Creating a strategy for your personal style can easily feel like an indulgence. So many clients have said that they actually save money by buying pieces they will actually wear and skipping the noise. That’s what the Poplin system is designed to do- give you the guidelines to purchase with intention so that you can make smart financial decisions.

Client Perspective: Jessica and Anneliese and Lauren and Chieni

I’ve never really been into clothes and now I just feel frumpy. I don’t think I want a major makeover, but maybe I do? I just don’t feel good about the way I’m presenting myself right now.

Solution

Over the years I’ve worked with several women who, “weren’t that into clothes.” For each of these women, something happened that caused them to suddenly be very dissatisfied with their style. With some it was a change in body, in others, it was hitting a certain age. What they discovered is that when they wanted help with style, their friend circle was just as frustrated as they were. Enter Poplin. Having the tools to confidently know what to wear, how to wear it and where to wear it eliminates stress and anxiety. It also helps gain confidence. Every woman is different and has different desires and needs. The key is making sure that you are honest with yourself about what you really want. Do you actually want to be the center of attention or be known as a stylish person? Or, do you really just want a simpler way to get dressed and still feel great about your look? Or both? The online personal profile is especially helpful with this one. But even starting with identifying your body type, colors and personal style will take you far.

Client Perspectives: Sarah and Toni

Poplin client Swathy.

I always thought that personal stylists were for wealthy people.

Solution

It’s true. Individuals with means often hire someone to help dress them. Poplin is different. It’s not about heading into a retailer and having the sales person pick out a great outfit. It’s about determining what is a great outfit for YOU based on your personal style, body type, budget, lifestyle and values.

Client Perspective: Amanda and Swathy and Roz

I really struggle with making changes in my style because whenever I do, the people around me either put me down or don’t seem to notice at all. Then, I just go back to the way I was doing it.

solution

This is SO real. In order to be successful at any endeavor, it sure helps to have a supportive community. This is why I suggest that clients venture out into the world with supportive friends or co-workers as we kick off the process. Nervous to try on those new knee high boots? Wear them out to dinner with a friend that you are certain will compliment you on them. Have a feeling that your critical sister will tell you that they aren’t age appropriate? She isn’t going to see those boots until you’ve worn them enough times to feel like you can take on the world. Set yourself up for success, My Dear. It’s all about progress, not perfection.

I experienced sexual violence or abuse in the past and ever since then, I just don’t feel comfortable in pieces that draw attention to my body. But over time, I feel like I’m hiding and it makes me feel worse. I’m not sure how to find clothes that make me feel confident and beautiful without making me feel like a target.

Solution

When a client shares this sort of information with me, I feel so honored that she’s comfortable with this level of vulnerability. As a sexual abuse survivor, I’m very familiar with this situation and didn’t start wearing revealing clothing until my late 30’s. For me, I find that limiting my choices based on the past experience continues to give the power to my abuser. If this situation is familiar, that approach may or may not resonate with you. Either way, we work together to find pieces that are within your comfort zone and find ways to give you your power back without making you feel uncomfortable. From my perspective, women really dress for ourselves first and foremost, then other women and lastly (if at all, men). But again, everyone has their own values and perspectives, which is part of the magic. Personal style should really reflect your values above all others.

Poplin client Hana.

Poplin client Vibha.

I’d love to wear fun clothes but my office is so conservative (or casual), so I just don’t bother. I realize it affects my self confidence and sense of power, but it feels like a really complicated problem to solve.

Solution

This one comes up all of the time, especially with clients who moved to Seattle from other cities, most notably DC, NYC or San Francisco. Women in tech seem to struggle with this one the most. Yes! There is a way to integrate your authentic personal style into clothes that are more casual or conservative than you might like. Design constraints often make a better product in the end. Take a look at Hana’s sweatshirts and skirts or Natasha’s effortless blazer with sneakers for some ideas.

Client Perspectives: Vibha and Hana

 

Poplin client Fiona.

 

I’m in the process of transitioning to female and figuring out my style has been incredibly difficult. As my body changes, I’m unsure what works for my frame or even what I should be looking for. Plus, finding retailers that will work for me is tricky, too.

SOLUTION

I started working with Trans individuals in 2014 as part of my volunteer work with YouthCare, a local nonprofit for youth experiencing homelessness. Those sessions led to work with Trans clients and I’ve been very grateful to have been a part of the style evolution of a number of Trans women. Whether a client is at the very beginning of her transition or has been living as a woman for years, we’ve discovered that having a strategy for shopping with clear guidelines, recommended retailers and more has a profound impact. If this is your situation, be aware that your body may change from one body type to another. Typically, men have Inverted Triangle, Rectangle or Diamond Shapes. After hormones and transition, those folks have new figures that are often Hourglass or Diamond silhouettes. Learning to dress for both gives you the freedom to purchase pieces and experiment with your look as things progress. Pinterest boards are also an extraordinarily helpful resource. Pin items that appeal to you, then review those to identify your authentic personal style.

Client Perspective: Fiona


I feel overwhelmed by the idea of solving my style problems. I’ve tried Rent the Runway and Stitch Fix, but neither felt like a fit. I didn’t know what to choose from Rent the Runway and Stitch Fix sent me pieces that were blah, at best. Plus, I saw other women in my office wearing the same items!

Solution

When Stitch Fix appeared, clients and friends asked me if I was worried that my job would become obsolete. Frankly, I wasn’t sure. But, over the years, these services have been a great pipeline for clients. Yes! Automated style delivery services are a great fit for lots of folks and as far as I’m concerned, that’s a win. Every opportunity for more women to feel in control of how they present themselves to the world is a victory. As it turns out, for many women who invest in a solution to their style conundrum without achieving the desired results, ends up more disappointed than if she hadn’t tried at all. In so many cases, we’ve discovered that a deeper dive with clear guidelines and freedom to be more creative is required. That’s where Poplin comes in. This is a teach you to fish model. Some clients, like Delight, never even buy new clothes. It’s just about editing out the noise and understanding how to maximize what she has. Other clients, like Ashley, limited themselves to second hand pieces and we tailored everything to make it ideal for her. Sarah’s wardrobe is predominantly sustainable pieces. This is a personal style cultivation process intended to be a skill that stays with you for the rest of your life.

Client Perspective: Angela

I really want to get some help with my style and I know this service is for me, but my partner doesn’t think it’s worth the money.

Solution

Let me leave this one to a portion of Poplin client, Tarah’s, Yelp Review.

"…I purchased almost every single thing off of my list, including a pair of faux leather skinny pants, which is very far outside of my normal comfort zone. But in the spirit of trying new things, I figured I would give them a chance. Well let me tell you, when I came downstairs wearing the pants to ask my husband if they were "too much", I got quite a reaction! His jaw dropped and he said, "Wow...that's one hell of a service! Worth every penny!" He REALLY liked the pants. And this is coming from a guy who never really says anything about what I'm wearing. I also noticed in the following weeks that he would randomly compliment me on whatever I was wearing and tell me I look nice. Such an unexpected, but welcome effect on my marriage! :-)…”

Poplin client Gwen.

Poplin client Lusha.

I just want to feel good in what I’m wearing. Do I really need a stylist to achieve that? Why can’t I figure this out on my own.

Solution

I had a client recently ask me why women don’t learn how to dress our bodies without having to work very hard to find the information. She had been struggling with this issue for years and as we went over her online personal profile, guiding her to pieces that flatter, she was both elated and frustrated that she hadn’t learned about this years before. I can’t say I blame her. It may be surprising, but there are hard and fast rules that help a woman know what is going to make her feel best about her overall look. So, if you didn’t learn those through osmosis, it’s not your fault. We often have a sense of what looks great, but when we try to replicate it with another piece, it falls short. This is because the characteristics of why this piece works are not what we think. This goes beyond whether it brings you joy, although that is clearly important. And once you know the rules, you know them forever. For starters, dive into the dressing for your body type Pinterest boards to get you started.

Client Perspectives: Rebecca and Amy and Gwen and Lusha

Poplin client Sarah.

Poplin client Ashley.

Sustainability is really important to me and I feel guilty about getting new clothes when I have pieces that are perfectly functional right now, even though I don’t feel great in them.

Solution

Agreed! Living your values really transforms the way you feel. At the same time, none of us are perfect, so just remind yourself that the goal is progress not perfection. Shopping with intention is a sustainable way to shop. It keeps you from purchasing pieces that you’ll never wear and even better, prevents you from buying items that you don’t feel good about, even if you wear them. Your current collection may be “functional” as in, you have something to put on everyday. Your clothes should empower you. They should make you feel confident and give you the extra push you need to be your authentic self. If they are doing that, it’s time to make a change. Also, establishing sustainability as a value means that you’ll opt for pieces that are aligned with that value, whatever the specifics mean to you. For example, you may opt for pieces made from recycled materials, those that are biodegradable, vintage or pre-owned items or those that take fewer resources to make or take care of. Stick with your filters when editing your closet and when buying new items: Does it flatter your frame? Is it in your color palette? Does it communicate your authentic personal style? Is it functional for your life? And does it align with your values and in this case your approach to sustainability? Check out Why Shopping with Intention is Good for You and the Planet.

Client perspectives: Ashley and Sarah

I have NO idea how to dress in Seattle. After moving here, I’ve discovered that I feel uncomfortable in anything with bold colors or prints, even wearing my red lipstick. Everyone is so casual. When I tried to wear hoodies and jeans, I started to feel really frumpy and I just don’t feel like myself. Plus, the weather! How do I look great when it’s pouring rain?

solution

First, ask yourself the question: Do I want to be the best dressed person in the room or just fit in with everyone else? Once you honestly answer that, you are in good shape. Of course, it’s important not to be wearing a prom dress to the office, so it’s all about finding pieces that are both appropriate for the situation but also make you look and feel amazing. Seattle is certainly changing as more people move here from other major cities around the world and our style is improving, for sure. I’ve worked with so many clients who found that as they tried to assimilate, they started to just feel depressed. Seasonal Affective Disorder is real and just wearing whatever is comfortable is not going to help. Instead, opt for pieces that make you feel good, even when you are at home. When you do that, you’ll want to interact with others and you’ll have more confidence. Check out What Can I Wear Besides a Puffer Jacket? and Pacific Northwest Style: What Can I Wear Besides my North Face Fleece? for some ideas.

Client Perspective: Becky and Aga and MB

It’s me!

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