Style Despite Sickness

I wanted to interview Sydney Lester of Chic Stripes because she has been so helpful to me as I try to wake up to fashion. Looking better helped me to feel better. And as I started to feeling better and feel more confident and more in my body, I started to feel even better. For once, I managed to create a positive feedback loop. Most of all, she guided me in changing my wardrobe so I am more excited to get up out of bed and get dressed!

And I am so grateful and she’s made such a difference in my life, I asked her to be my first feature in my new interview series, Back to Being. She truly helped me get back to being stylish and feeling more alive and beautiful.

Sometimes for me getting dressed in the morning means I just change clothes into other lounge wear. That’s on my bad days. But under her guidance, even my lounge wear has been streamlined and updated. As a result, on those days when I shift from my sleep wear to day wear to continue to rest in, I don’t feel like such a loser. (I’m not quite at the level of these glamorous classic movie stars, but I continue to aspire! Scroll down to “My Idols.”)

What I love most of all, though, are what I learned about how to change my wardrobe, how to shop, how to be more mindful about both my closet and what I wear. I look better, while spending less money on my clothes. I enjoy easier decisions every morning as my closet is more streamline. Mean and lean! And beautiful. And making me feel more beautiful and more worthy.

I hope you enjoy the amazing chat I had with Sydney all about the obstacles that we, who are living with illness, often face when we begin to think about our style.

About Sydney Lester of Chic Stripes ::

Photo credit: Sarah Walor

Photo credit: Sarah Walor

Sydney is a personal wardrobe stylist with over 8 years of experience in the fashion industry. In 2009 Sydney launch Chic Stripes, her personal style blog that focused on creating individualized style by shopping second hand first. She parlayed her blog into a successful personal styling business where she works with women and men to create sustainable and timeless wardrobes that work for them and not against them. Sydney has been featured on numerous television programs and worked with both local and national brands. She has been interviewed by the Wall Street Journal and the Today show, too!

What We Discussed ::

Sydney and I had a terrific discussion on the 5 main obstacles that often come up for women who live with chronic illness when trying to get dressed or to be more stylish.

They are ::

|| Obstacle 1 - We don’t have the energy to shop. Energy and ability is our hot commodity, and spending it on shopping is often not feasible. After a trip to the mall, we can be flattened for days.

|| Obstacle 2 - The changes in our body, either gaining or losing weight or weird rashes or pop up sensitivities, makes us feel “not in our body.” We don’t have the same body as we did before we got sick. Clothes don’t fit as they did. So we just give up.

|| Obstacle 3 - We say to ourselves, “I don’t have a life, I have no where to go, I have no social life - so what’s the point in trying to be stylish?”

|| Obstacle 4 - We have other, more critical priorities other than worrying about how we look -- like how to eat, getting a shower, or sorting that huge pile of mail.

|| Obstacle 5 - Sometimes, frankly, we want to look as bad as we feel. We want the outside to match the misery on the inside. When you have an invisible illness and someone tells you, “hey you look great!” you can feel not truly seen, when inside you’re in immense pain and can barely stand up.

Here’s the video ::

Q + A With Sydney ::

Sydney is so generous with her time and counsel; she agreed to answer some additional questions for you on style in general and style for women who live with illness.

How did you decide to become a stylist?  

Photo credit: Sandy Swagger Jones

Photo credit: Sandy Swagger Jones

It all started with a blog in 2009! I loved this idea that people could express themselves through clothes and wanted to try it out myself. Through blogging I learned that styling was a thing and I also found out I was good at it (a skill set not everyone has!). I took classes and started practicing with friends + family. Styling for me grew naturally! I think the most important thing was that I took the first small step to explore something I was interested in - never in my wildest dreams did I think it would be a business.

How do you feel your background in social work affects how you help people improve their style?

My social work degree is in the macro area - addressing large systems - and not what people traditionally associate with social work - the direct work with clients. But because I’m big on TEACHING my clients how to systematically address and change their personal style, it fits nicely! I believe that when you can change issues at their core, then you can enact change on a larger scale.

For example - so many of my clients surface level issues are hating shopping, feeling frustrated with getting dressed, but that often stems from a lack of self-confidence, not feeling good physically, or or from what someone told them they could or couldn't wear. By digging into these things we can start to slowly but surely make change.

Why is style important?

It changes the way you feel and therefore how you think about yourself.

Is style - the process of maintaining style - antithetical to comfort and ease?

Not at all! Maintaining a personal style is ALL about figuring out what comfort and ease does mean for you and how to translate that into clothing that has an upgraded quality about it. And being okay with knowing this can change over time.

For example - I have ankle boots I LOVE and wear nearly daily. They have a 2.5” heel which is starting to wear on me and not be super comfortable. So the next iteration of my style is to find super cute, stylist and comfy sneakers and flatter boots. It’s all an evolutionary process as you evolve and go through life and your style journey.

Is style hard to maintain?  

It’s not hard, but like anything worth having or doing, it does take planning and consideration. That’s why I love my lists and structured process of addressing style. Cassandra note :: I love her methodology too!

It gives you a framework to continually assess your style and make small changes as needed. Smaller changes can be more effective and less stressful than one big, bang-out overhaul.

Sydney at work [Photo Credit : MoPic's Photography]

Sydney at work [Photo Credit : MoPic's Photography]

how can I have style on a limited, sometimes very limited, budget?

Go slow! Invest in yourself and giving yourself a style education. Know that you don’t need to do it all or buy it all in one fell swoop.

Again, it’s a journey! Look into consignment stores. Buy things on sale. Shop online and utilize discounts, free codes, etc.

What is your philosophy regarding style trends?

Don’t do them. The only exception is that you love something so much that you’ll continue to wear it long after it’s “out of style.” I tend to recommend classic pieces and solid colors because they stand the test of time. I like to intersperse and amp up personal style with a signature color or look (i.e. blazer, skirt with tennis shoes, vintage jewelry, scarves) vs. putting money into trends. Cold shoulder tops are my nightmare!

What are some of the reasons your clients hire you?

They just getting dressed to be easier. Straight up. People ARE tired of trends. They have too much and they don’t know how to make it work. They want less. They want to make fewer decisions. My processes help them learn how to streamline their wardrobes.

What have been some of the most gratifying or satisfying moments of your work?

When clients text me outfits they put together themselves. That brings me SO much joy because it means they are learning and as a teacher, social worker, and stylist - it means I’ve done my job well.

Photo Credit : Tim Win

Photo Credit : Tim Win

If you had three tips for women who - because of their physical limitations - find shopping in person a luxury what would those be?

  1. Make your list and do targeted specific shopping to save your energy.

  2. Treat yourself - whether that’s a coffee or tea afterwards, a message, or even a nap, create space for yourself.

  3. Give yourself permission to make purchase AND RETURN THEM if they don’t work.

What is Style Camp?  How does it work?

Style Camp is a is a transformative six week virtual guided program to find, hone or reset your personal style.

It’s an online program with 12 prerecorded video lessons, exercises, a workbook and live calls to guide you on your style journey! I walk you through the process I use with my in person clients and teach you skills that will honestly last you the rest of your life.

Learn more about Sydney’s Style Camp

What are the benefits or outcomes of Style Camp?  

Before I took Style Camp, I had a vague sense that my “sick wear” affected me in unhelpful ways, but I really didn’t have clarity about how or why or what to do about that.
— Cassandra Marcella Metzger

Once you enroll in Style Camp, you get the materials. Plus any upgrades or additional improvements I make are yours for life! You can do all the calls, keep engaging in the FB group, and that’s SO valuable.

You aren’t just given the materials, have 6 weeks to “get it” and then get let loose into the wild of shopping malls. You’ve got support.

Specific benefits include:

  • Understand body type measurements and how to use them,

  • Reduced shopping stress,

  • Master tricks of the eye to shift proportions,

  • Discover other resources for good quality and comfortable clothes,

  • Know how to clean out your closet (without being overwhelmed by the mess), and

  • Streamline your closest so to maximize fewer options and make better, easier decisions.

I am in Style Camp and absolute love it. The value is amazing, and I hope you’ll join me.


  • Have you given up on considering how you dress?

  • Do you ever dress down so that you look as bad as you feel?

  • How has your wardrobe shifted since you got sick?

  • What is your favorite item of clothing to wear?