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How to Create Winning Outfits

Building a Wardrobe
March 5, 2019

Welcome to Dressed for My Day where my goal is to inspire and help women like you and me to dress beautifully and appropriately for our unique days so we can engage gracefully with those around us and influence them positively. Today we’re continuing our 2019 style series, Building a Wardrobe that Works for You. Specifically, let’s talk about how to create winning outfits from the pieces in your closet.

How to Create Winning Outfits

Let’s Go to the Movies!

Hang with me. This may seem like a diversion, but really it’s an analogy that I think will serve you well when it’s time to create those winning outfits.

One of my favorite movies is Raising Helen. Kate Hudson stars as a young woman who is not quite through sowing her wild oats or building her career when she’s suddenly given the responsibility to raise her recently orphaned young nieces and nephew. Great storyline,huh? But even the most intriguing plot won’t get off the ground without a stellar cast. Fortunately, Raising Helen was well cast.

Hudson shines in her role because she’s beautiful, sweetly authentic and convincingly naive. But John Corbett, who plays her love interest – a likable protestant priest, provides the necessary juxtaposition to Hudson’s wild-child appeal. And one of my all-time favorite supporting ladies, Joan Cusak, adds a delightfully quirky tenderness to anchor this funny but also poignant and moving story.

It turns out, strategic casting is fundamental to creating a winning flick. In the same way, we need to carefully choose the “cast” when creating winning outfits – outfits that captivate and tell your story beautifully.

The Story

Before we cast the pieces of the wardrobe, let’s understand that the story they’re all showing up to tell is…you. You are the story. Your outfit should say what you want it to say about you. Your outfit should also draw attention to your face and present your body in the best light.

You are the story.

Choose One Star

To cast or create a winning outfit that tells your story, you’ll want to choose one piece that will really shine. This one piece is your star. Remember, you generally only want one star in your outfit.

What makes a piece a star? This is the attention grabber, the article of clothing or accessory that you know will tell your story and garner the compliments.

But, just as director Garry Marshall undoubtedly chose Kate Hudson for the role of Helen because he knew she was suitable for the storyline, you want to select a star that’s suitable for you.

The trick to consistently creating winning outfits is to have the right stars in your closet. So as you build your wardrobe, carefully select a few pieces of clothing or accessories that can carry the role well. Honestly, if you build a wardrobe and don’t have any stars in it, your outfits will seem boring and you’ll struggle to create interest. But if you have a closet full of stars, you’ll just create drama when it’s time to get dressed! Know what I mean?

When you’re shopping and you come across an item that’s a potential star, audition the piece by asking these questions:

  • Is it in one of my signature colors?
  • Is it versatile? Can I dress it up or down?
  • Will it work well with my supporting cast (more on that in a minute)?
  • Does it suit my personal style?
  • Does it highlight my body in the right place? (Consider your body shape, proportions and unique body variations.)
  • Does it tell the right story? Do you feel like you when you wear it?
  • Is it a comfortable fit?
  • Am I a real fan? Do you love it?

The Supporting Cast Is Just as Important

While I like Kate Hudson, I love the movie because of the roles played by John Corbett and Joan Cusack. In fact, for me, it’s often the supporting actors that make or break a movie.

It’s the same way with a great outfit.

The supporting cast in your closet is made up of your wardrobe essentials. That’s why they’re essential. You might want to check out my list of Spring Wardrobe Essentials, and I’ll be supplying a similar list for summer, fall and winter this year.

Meanwhile, here’s a very basic list of wardrobe essentials that you’ll generally need to support the stars you add to your closet: (subscribers have access to a more extensive list in the Freebies for Subscribers.)

  • dark denim
  • trousers in your two chosen neutrals
  • a little dark dress
  • white or beige tops – blouses, tees and tanks
  • solid tops in your signature colors
  • flats in your neutrals
  • heels in your neutrals
  • nude heels and/or flats
  • basic jackets for your style aesthetic
  • neutral handbags

Finally, remember casting is everything. Consider these two tips for casting stellar supporting players as your wardrobe essentials:

  • Don’t select boring supporting players or essentials. Joan Cusack is anything but boring. Choose basic pieces that fit the definition of a supporting player, but select pieces with character and interesting features. Still, steer clear of too much embellishment. If there’s too much going on they’ll battle it out with your star for top billing!
  • Choose high quality supporting players. These are the pieces you’ll be cycling through your outfits frequently and for a long time. Choose pieces that wear well, that are constructed of quality fabrics and that have a classic appeal.

Invite Some Guest Stars

Think about your favorite sitcoms. You love the star and the ensemble cast is delightful. Such chemistry! James and I enjoy Wings, Everybody Loves Raymond and The Middle. (I know. We’re old.)

But every now and again, a guest star comes onto the show to play an interesting cameo role. They don’t necessarily show up in every episode, but when they do, they shine.

Likewise, your wardrobe should probably include some guest stars. These are often trending pieces. Maybe they’re pieces of clothing with interesting prints or louder colors. Maybe they’re pieces of jewelry that draw more attention to your face. They could be interesting shoes, belts or handbags. They’re not the star, but they get a lot of attention and add interest to an already stellar cast.

Pulling the Cast Together

So how do you actually use your stars, guest stars and supporting players to create interesting outfits? Let’s talk through what I did in these outfits from recent posts or selfies.

Green, Navy and White Spring Trio
white jeans (I’m wearing the size 6 or 28 curvy fit) || green wrap top (size 8) || navy ponte knit jacket (size 8) || leopard print block heels || satchel (similar)

In the outfit above (featured in this post), the green wrap shirt is the star. Its vibrant color, ruffled edges and wrap feature draw the attention. And really, it tells my story because it makes my green eyes even greener.

The basic navy jacket, white jeans and structured bag carry on quietly but elegantly in the background. These three essentials are my supporting players. I’ve invested in these and they serve me well consistently and often.

Finally, the leopard print shoes and interesting necklace could be considered the guest stars. I don’t want all the attention on them. Hey, look up here at my eyes! So, while they do get a little notice, they don’t detract from the star or from my face.

A Trench Coat for Spring
trench coat // high rise skinny jeans // chambray shirt // silk scarf // D’Orsay flats // handbag (similar)

I featured the outfit above in this post. Here, the trench coat is the star when I’m wearing it. When I take it off, the floral silk scarf (a guest star) takes over, drawing attention toward my face. The striped D’Orsay flats could also be considered a guest star, while the jeans, chambray shirt and navy bucket bag are all classic supporting players.

Notice that my supporting players are all in one of my chosen neutrals and they’re of high quality. Are you starting to see why those essentials are so…essential? Really, they create the stage for the stars. But if your essentials or supporting players are not “good” at what they do, the story is lost.

How to Style a Column of Black Between Spring Colors
Nic+Zoe Wonderstretch Pants (size 8) // Seam Detail High/Low Sweater (size small) // boyfriend cardigan (also available in black) (size small) // tortoise shell link necklace (similar) // Leopard print foldover clutch // Gemma Pointed Toe Heel Pumps (TTS)

In yesterday’s post I shared this column of black bookended by this beautiful green boyfriend cardigan. Obviously the green sweater is the star of the outfit. But what really makes this long cardigan the star? Remember, stars are stars because they’re good at telling the story. This sweater both creates a long, lean silhouette when draped over the column of black and draws out the green in my eyes.

The tortoise shell necklace and leopard print clutch are guest stars. They’re interesting, but they don’t detract from the star or the story. And the black sweater, trousers and heels are all beautiful supporting players.

That’s a Wrap!

I hope this post gave you some tools for creating winning outfits. Truly, creating a winning outfit is a lot like directing a scene in a movie. Keep the story central. Sure, choose some good actors, um pieces of clothing and accessories. Select a star, invite in some guest stars and utilize your supporting players. But don’t let any of them steal the show. It’s about you, not the piece of clothing, my dear. You are the story.

Blessed for My Day

While I want my clothing to tell my story, I really want my life, my words and my ways to tell His story. We can do that best when we decide consistently to bring Him glory. What does that mean – to bring Him glory? What does it mean to glorify God?

To glorify God simply means to give an accurate picture of Him to those around me. It means to represent Him correctly. It also means to reflect His character in all that we say or do. So when we demonstrate His character – love, kindness, grace, righteousness, patience – to those around us, we are glorifying Him. Daily I must ask myself if I am telling His story well.

Or do you not know that your body is a temple of the Holy Spirit within you, whom you have from God? You are not your own, for you were bought with a price. So glorify God in your body. ~ 1 Corinthians 6:19-20

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xoxo, Kay
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17 thoughts on “How to Create Winning Outfits

  1. Kaye, love this post! I love the analogy you use as it’s easy to see how an outfit can compare to a movie. Your post has given me lots of food for thought. Well done! Now off to check out the “cast” in my closet!

  2. A friend once told me that she enjoys my analogies, and until then, I didn’t realize how often I compare things to help myself understand and process information. This post illustrates a wonderful tool I know I’ll be using in the future. By getting the right “cast” I can take a good outfit to great, and all the while keeping true to the story, which is me. I LOVE THIS!

    1. Hahaha! I’m glad I’m not the only one who does this. I think my brain is just wired for analogies. I’m grateful you enjoyed the post. ?

  3. Oh, my! Your “Blessed for My Day” is beautiful. I am going to use it to frame my Lenten devotional time beginning tomorrow. Today: How do I plan to glorify God? Yesterday: How did I glorify God? Where did I fall short? What can I learn from that experience? Thank you and have a blessed day!!!

    1. Ah, I’m so glad that spoke to you Diane. May your Lenten season be a blessing to you as you prepare your heart for the beauty of resurrection Sunday.

  4. Thanks for sharing a very creative post, loved how you used a movie! Great outfits too, have a blessed day!

  5. Love this analogy. Thank you for taking the time to explain the process in a way we all can understand.

  6. Thank you for this post Kay! What a wonderful way for me to view the pieces hanging in my closet. I definitely have some work to do on the supporting roles. What a great BFMD!

  7. Hi Kay,
    Great post! Easy to see how important each part of the outfit is when you compare it to a movie!
    Love your green sweater! And the Blessed for my Day!

  8. Kay- you spoke right to me today. Thanks for sharing your ideas and your philosophies about making the movie ‘star’ the wearer. Well done!

  9. Crazy, silly, or smart-definitely SMART! This analogy is so simple, yet eye opening! I’m going to use it every day! I was in medicine prior to retirement and often explained difficult diagnoses to patients using analogies. I think like you. This is easy to remember technique to employ every time we get dressed!

  10. Thank you so much, this was so educational and a great way to remember how to pull together any outfit!!
    Pictures helped as well of past posts.