How to Build a Wearable, Workable Wardrobe!

August 7, 2025

This is an updated version of my comprehensive guide to building a wardrobe that really works for you and your lifestyle! 

 

This is an outfit created by following all my own suggestions: neutral colors in personally flattering silhouettes, with a pop of my favorite accent color.

I’ve done a series of blog posts about wardrobe building, so if you’re a regular around here, some of this will be familiar to you.  But I thought it would be a cool idea to distill all that information into one handy easy-to-work-with blog post. I’ve also added a few new thoughts and ideas, as well as updating the photos of course.

 

Lifestyle

Lifestyle is what you’re doing every day and how you are living your life. Are you a stay at home mom? A high powered attorney? A wanna-be actress? An emergency room nurse? … Are you retired and traveling? Writing a novel? Building a business? …Do you go to fancy parties? Or casual get-togethers? Or maybe you’re strictly a homebody? Think about what you do and where you go and what you dress for.

My Lifestyle

For example, personally I dress for teaching school five days a week. For that job, I like to be stylish and comfortable, professional, but approachable. On the weekends, I never know what what my husband and I are going to be up to. It used to drive me crazy that he didn’t like to plan, but I’ve come around to the fun of deciding on a whim. That means though that I need to be dressed for just about anything, or at least have an extra pair of shoes in the car. We also treasure our at-home time, puttering around, watching TV and movies, playing with and walking the dogs, so I like to have cute and comfy loungewear for all that. And I love to glam up a bit for a lunch and shopping dates with the girls or blogger events!

 

This is a typical outfit for a day of teaching school.

Identity

What you wear sends a signal to the world about who you are. I don’t think that’s overstated at all. And most importantly, we tell ourselves who we think we are by the way we look and dress. What message do want to convey to the world? And what message do you want to be sending yourself everyday?

Identity Crisis = Style Opportunity

As our identities change over time, so does our style and our outfit choices. My biggest style crisis was when I moved into middle age and felt that I no longer knew who I was style-wise. Dawn was always all about the junior section. How was I supposed to dress as a midlife lady? Now in my life, I identify as a fun, funky women of a certain age, someone confident in herself and excited about this chapter of her life.

Describe Your Style

How would you describe your style? Boho? Preppy? Modern? California casual? Edgy? Minimalistic? Classic? Sophisticated? Whimsical? Fun? Funky? Elegant? Feminine? Androgynous? Retro?

Is there a decade that inspires you more than others? Is that a particular mood that you’re attracted to? Who are your style heroes? Jackie O? Stevie Nicks? Audrey Hepburn? David Bowie? Grace Kelly?

I like to play with different attitudes with my clothing, but I also feel like I have a root to my style. I would describe my style and wardrobe as elevated modern basics, very casual California, with a bit of an edge.

 

I think this unique combination expresses my personal style.

Silhouette

The outline and shape of a garment can make all the difference in how you look and feel in it. Most of us look better in some silhouettes than others, and of course there will be a few fortunate women who will look great in any silhouette.

There are generally considered four basic body shapes, and every single shape is beautiful!  And every shape comes in every size and I truly believe every size is beautiful too!

With age, your body will change of course.  Your basic shape will stay the same, but after menopause, the weight will shift more to the tummy area.

Apple

If you are an apple, you probably have a great bust line and fab legs and these are the pretty parts you want to show off.  Your waist is undefined and you carry any extra weight in the stomach area. For tops, you will look great in A-lines, flowy tunics, button-ups, and V-necks.  Sheath dresses are also your friend. Just be sure to keep clingy fabric and big thick belts away from your waist and go ahead and play up those great legs and pretty cleavage.

Pear

If you’re a pear shape, I am one of your tribe. Pears carry weight in their hips, thighs, and butt.  Pears usually have a defined waist and pretty shoulder line.  In general, fit and flare and A-line skirts and dresses are your friend and are easier styles to fit. Boot-cut and flare pants bring balance.  Jackets and coats are best if they hit between the waist and the hip bone, or below the booty. Add balance with color and interest on top and simple bottoms.

Hourglass

An hourglass figure is curvy with a defined waist. In the hourglass shape, bust and hip measurement are roughly even.  The hourglass shape looks amazing in more structured silhouettes. Hourglasses look to die for in dresses and I would definitely suggest the fit and flare and the classic wrap dress.  Show off your small waist and when in doubt, belt an outfit!  Avoid anything boxy or flowy. Remember you’ll look your best when you show off that nice waistline.

The Stalk

Usually called the stalk or the banana, this shape is basically straight up and down.  In 1920’s and again in the 60’s your body type was all the rage!  Skinny or straight leg jeans are your friend.  You will look great in a sheath dress. If you wear a flowy dress, a belt can add a waistline. Ruffles and details at the bust and hips can add more volume there.

Fit

I can’t stress enough how important the proper fit it for a garment.  It can make all the difference.  Most items should glide close to the body, without stretching or pulling too much.  An affordable local seamstress is precious! Also, never let your pride get attached to a size.  Sizes so inconsistent, plus bodies change and that’s okay!  Love and dress the body you have right now.

 

Color

The basic rule for wardrobe building is to pick a few neutrals that look good on you for basics and then pick an accent color or two.

What is neutral? A neutral is a color that mixes well with other colors.

List of neutrals:

black, gray, white, ivory, beige, taupe, tan, brown, khaki beige, khaki/olive green, navy, denim

Accents colors:

red, orange, yellow, purple, blue, green … and all the pretty colors in between.

How to pick your best colors?

Well, when I was studying fashion in college in the 80’s, the seasonal theory of colors was all the rage, and it seems to have recently come back into style.  It’s a fun theory and worth checking out, but just like body shapes, there’s never exactly a one size fits all. 

But again, this is only a starting place. I think most of us know what colors we feel best in. What shades do we wear when we get the most compliments?  What color are you wearing when someone asks you if you’re tired (and you’re not!).  If you really don’t know, ask a savvy friend or go or get your colors done!

Some colors may look better or worse on you if you change hair colors (including going gray), but mostly your colors are based on your skin tone which stays more or less the same.

My basic neutrals are black, gray, tan, and denim.  My favorite accent color is my favorite color period, red!  I love all the variations of it as well, from an orange-y red to a hot pink to a deep burgundy.

Budgeting

Even the best shoppers forget this important consideration. Oftentimes we have no idea how much we’re planning to spend on our clothing this season or this year.  We buy on a whim, which can be super fun in small doses, but it’s not a sustainable way to build a wardrobe.  Take stock of what you have and what you need.  Think about what wardrobe staples you have that are flattering on you and what you will need in the season to come.

 Cost Per Wear

The idea of cost per wear is a helpful tool to help you decide where to spend your clothing dollars.  The idea is to take the price of an item and divide it by how many times you’ve worn it (or will wear it).  I challenge you to try this for a couple of key pieces in your wardrobe right now! Items that are basics, modern classics, that you will wear on a regular basis, are definitely worth spending more money on.

 

Cost per wear example: This well-made black blazer cost $200. I have worn it about 100 times, that means it’s about $2.00 each time I wear it.  But, I still love it and that cost will be even lower by the time I get rid of it … or it falls apart!

On the other hand, I bought some beautiful red suede boots for $200. I thought I would wear them more often, but honestly, I’ve only worn them twice.  That means the cost per wear is $100.  Still gorgeous boots, but not a great deal.

Shopping

I love the ease of shopping online. You have so many more choices and your package magically shows up at your door! If you’re not sure about a fit when you’re ordering online, make sure you check out the size chart and make sure returns are easy to do.

But there are times to get yourself to the store in person as well.  And sometimes, it’s fun to just go to a store or mall and try on lots of different things!

Whether in person or online, it’s always best to have a list. I keep a digital note to myself with a list of things that I’d like to add to my wardrobe. It helps keep me focused.

Sales

Never buy something just because it’s on sale. That’s never a good enough reason! New items come out before the next season and modest discounts will start about halfway through the season.  Deep discounts will start at the end of the season. January is the best time to get deals on fall/winter basics and August is the best time to get deals on spring/summer looks.  However, if an item is super trendy, you probably want to get it at the beginning of the season so you can wear it before the trend is over.  If you find something you love at the beginning of the season, something that you need for your wardrobe, it’s well worth paying full price to make sure you don’t miss out on it.  I’ve waited before and then couldn’t get my size.  

Your Turn

To wrap up, I’d love to hear your tips for building your own workable, wearable wardrobe.  Feel free to share in the comments.

…And remember, my newsletter subscribers can always get free stye advice via email, so if you haven’t yet, sign up!  (Your email is always safe with me.)

 

Fun & Fashion

Dawn Lucy

About the blog: Fashion Should Be Fun is ME talking to YOU, other middle-aged women who are over 40, but not over fashion.  We still want to look beautiful and stylish.  We still want to have fun with trends.  And we don’t need anyone giving us rules, because we’re all different. This is a place for me to share my love of fashion with you, including style ideas, tips, trends, and inspiration. I know how liking the way we look can translate into confidence and energy. I know we have so much life left to live and so much adventure ahead of us. Let’s show the world you’re never too old to have fun and look fierce!

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