Not being good at something can be frustrating. Yet the triumph over these things we find difficult can be so incredibly rewarding. It does, however, take focus, commitment, a willingness to change, and sometimes seeking help, to overcome.

Fashion is hard for more women than you probably think it is. Often, how I describe clients who come to me for help are typically very successful, intelligent, sometimes type-A, high achievers who are good at most things and stymied by the fact that they can’t master being fashionable. I assure them all they are the norm, not the exception, to struggle with getting dressed.

Fashion Tips from The Formerly Unfashionable

Not everyone has the budget, need or desire to overcome the challenges of being unfashionable by hiring a stylist like myself. It’s not a path that is right for all. So I asked the members of my Facebook Group, who once considered themselves unstylish, for their tips on what they did to overcome it. Below, I have summarized some of their responses. If you are a member of the group, you can read all their answers in full here. Not a member and want to join? Click here for more information. If you are on the journey of overcoming being unfashionable, these realistic tips from these amazing women who are further along the path can help.

Tip #1- Authentically Embrace Yourself

These amazing women learned the importance of authenticity and the courage to embrace who they are. Never discount this as an important step in becoming fashionable.

I began to understand that the clothes did not make me, but, instead, I made the clothes. So, instead of latching onto the fast fashion of the moment, I am now concentrated on finding the pieces of clothing that I like and that I feel good in. The best lesson I learned through my journey was, dressing for success, whatever that success is, is not a specific type of outfit, it is dressing in something that makes YOU feel good, thereby inducing you to feel successful.

“A few years ago I took a trip to New York and had exposure to a wider range of fashion choices/risks on real people than In my small California town. It was inspirational! I was encouraged to try different looks, take more risk with clothing choices, and showed me that it is ok to not look like everyone else.”

“I started caring less about what others think. I wear what feels right and what flatters my body in a way that makes me smile when I look in the mirror. If it’s not what’s hot or what’s trending right now, I don’t care. When I leave the house and feel great about my clothing, it’s going to be a great day.”

I don’t consider myself stylish, however, I am comfortable with my own unique style. My transformation has been a slow progression and I continue to tweak it but am no longer trying to fit someone else’s mold. The biggest hurdle for me was allowing myself to be myself and not be dictated by anyone else.

“I sat next to a woman today who was where I was a year or two ago – tennis shoes, jeans, sweatshirt – and I realized how much better I feel for making an effort. For me, it was just pushing outside of my comfort zone and prejudices.”

“I stopped dressing with the purpose of hiding myself. My clothing choices are my outward expression of joy.”

 “I did a closet edit where I carefully collected data on myself—sort of like Marie Kondo but for everything that “sparked joy,” I documented its characteristics. As a data nerd, that allowed me to identify the patterns of the things I like and feel confident in.”

“I stopped trying to emulate women I admired and took a long, hard look at myself: my coloring, my body (all 4’11” of it), the hair I had always hated, all of it. And I stopped focusing on all my perceived flaws and started to see a set of assets to be brought forth.”

 “I started trusting my instincts more. I stopped wearing what colors and styles others thought I should wear. And started wearing things I thought looked good on me.

Tip #2 Work with your body, not against it

It can be hard to accept a body you wish was different and it’s important to understand that even the most body-accepting women still have their moments of struggle, but I assure you, body acceptance is a crucial part of the journey of becoming fashionable.

“I’ve reduced / replenished my wardrobe with things that genuinely make me look like how I want to look.”

I learned what proper fit is.

 “Learning about body types, and figuring out what works for mine.

I finally figured out what looked good on my figure. Not always my style choice but correct. Then purchased and have tried to embrace.”

“Understanding colors, and what feels good on me.”

Finding the right kind of top layering for my shape has been a game-changer for me the last couple of years.  I love what adding a trendy jacket to a classic/basic wardrobe and how stylish/smart accessories can get me through what I hope are decades of fashion cycles.

Analyzing my body shape so I had a much better idea of what shapes, fabrics, lengths, etc. looked best on me enhancing my good points and de-emphasizing the ones I didn’t want to highlight.

The biggest help to me has been first finding bloggers with similar body size /shape proportions ( Jean Wang from and Kelly from and learning how to wear professional /casual clothes that make me look like an adult rather than an adult who still shops in the junior dept.

Being in a wheelchair, I ask for the bigger fitting room in the store, sit in the wheelchair while trying on clothes, and take my time while looking at myself in the outfit I am trying on from every possible angle, all while sitting in the wheelchair. I am not young. I am not supermodel material. I am not able-bodied. Clothes do not define who I am. But clothes can help to bring forth aspects of my personality.

Tip #3 Get outside help

It is assumed that being fashionable is encoded in their DNA. It’s not. If it were, I’d be out of business. There is nothing wrong with asking for help, in fact, asking for help is a sign of strength, not weakness. I happen to be good with fashion but assure you, there are LOTS of things with which I have needed help. These women weren’t shy about looking outside themselves, be it books, blogs, hiring someone or watching popular makeover shows, to become fashionable and as a result, they have reaped the benefits.

I bought and read lots of books on color & style, read many online blogs, & watched far too many episodes of What Not to Wear.

“I read multiple style books, had my colors done, repeatedly, followed multiple bloggers my age, including several from UK and elsewhere in Europe, used image consultants, live and virtual. I found that it’s hard to train your eye to see something different when you look in the mirror.”

I invested my time in myself. I read a few fashion blogs for advice and inspiration, but mostly I spend time in dressing rooms playing trial and error.

I hired a local consultant to go through my closet and take me shopping. I bought everything. There was an instant change that was marked by others in my company.

I started learning more by following blogs or Youtube channels devoted to fashion, especially those giving reviews, and putting some time into reading.

I started with Project 333 and used that to help me narrow my closet and the Get Your Pretty On challenge. I read the Vivienne Files to get a sense of creating cohesive wardrobe capsules using a pattern in a scarf or top to derive the color palette for the rest of my outfit.

 “I spent time on several blogs, like Inside Out Style and You Look Fab, that have very specific advice about shape, size, proportion, etc. I spent a lot of time puzzling out my style, which I have a much better handle on.”

 “I found your blog super helpful for learning about accessories and a pop of color… this has been super helpful!!!

Tip #4 Less is More

When you are trying to figure your style out it’s easy to fall down the rabbit hole of buying more and more. The only thing this does is jam-pack a closet with unwearable buys. These smart ladies took a different approach and pared-down instead of piling up.

 “It was learning that it wasn’t necessarily about the number of clothes in my wardrobe, but more about selecting quality and tailored pieces that were versatile enough to work together to mix and match into several different looks using the same pieces.”

“I significantly limited the options available to me in my wardrobe — colors, silhouettes, prints vs. solids, styles, etc. — experimented with these limited options and took copious notes. It’s awfully hard to assess any experiment when there are too many variables. A stew with 100 ingredients might taste terrible, but with so many ingredients, it might prove impossible to fix the recipe. A stew with ten ingredients can be fine-tuned to culinary perfection.”

“I’d say I limited my choices to those things that look good versus “I love that.” I realized all that I love does not love me back… fit is everything…. I’ve scaled back to fewer colors with more repetition… even revitalized my accessories – removed similar or duplicates.”

“I learned how to recognize when to throw away worn-out clothes.”

Tip #5 Expand your color palette

When we don’t know what to do, we go for the obvious fixes. In fashion, that often means buying black. It’s hard to fail that way. There is nothing wrong with black, but when it is selected as a fail-safe, it can create more issues than it solves. These women dared to expand their color palettes.

“I started reducing the color black in my wardrobe. Which helped me in noticing other color combinations.”

“I’ve become aware of the fact that I can deviate from black. Also, I’m improving on my concept of what I really wear, as opposed to what I think I’ll wear in some imaginary world.”

“One is to experiment with color and not limit myself as far as styles go just because I’m a petite 5’1 67 y/o senior. I think what I like the most is the “capsule” idea of putting outfits together with the right accessories.”

Tip #6 Trial and Error

Lastly, don’t be afraid to fail. If you’re not failing you’re not growing. Yes, it is frustrating when you feel like you are taking one step forward and two steps back, but nobody learns when they don’t try something new.

“I take a picture of an outfit to get a sense of scale and proportion. I actually have a spatial learning disability that manifests itself in a few strange ways. Taking a photo puts things in a 2D form that helps me interpret what I’m seeing better, and helps me form an opinion about my outfit.”

Do you know how I learned how to knit this?

By learning how to knit this.

My point is, you can’t get to where you want to go without starting somewhere, even if it is really rudimentary. I couldn’t knit an extensively cabled sweater if I didn’t have a handle on the basics. So wherever you are on your journey, you are right where you need to be.

Thanks to my Facebook Group members who generously shared their strategies to help other women develop their own.