Over 50? How to Put an Outfit Together with Confidence

Last Updated on March 1, 2024 by Candi Randolph

The question of how to put an outfit together as women over 50 is influenced by a number of factors, including where we are in life, how we see ourselves, and the priority we give to fashion.

We’ve lived a lot of life by the time the half-century mark passes, and so we know many things. We’re wise. We’re experienced. We’re confident.

How to put an outfit together as a woman over 50

But sometimes it feels like we’ve forgotten how to get dressed in the morning. No, I don’t mean that we can’t figure out which is the bottom and which is the top. (We’re in big trouble, girls if that’s the case.) Rather, we have lost confidence in our ability to style ourselves.

For some reading this, the reaction may be ‘pish-tosh, I love fashion, styling myself, and I rock my looks’. That’s awesome!

For others, though (and I know you’re out there because you tell me about your frustration), as our bodies have aged and changed, we’re not sure how to put an outfit together and know we look our best.

I’ve created a helpful printable for you to keep as a handy reference when putting together an outfit. More about that later. I don’t know about you, but I need something to refer to because I can’t remember everything I read in a day, much less over a period of time.

In our 50’s and 60’s, we may have said goodbye to the career, so dressing for work is no longer part of the process. Our bodies have changed, adjusted, expanded, rearranged, and those business separates may not fit as they once did anyway. Actually, everything we own that isn’t stretchy or baggy might be less than comfortable to wear in this stage of life. Not trying to be a Debby Downer, it’s just a fact.

Our schedule is more flexible, though. Yay for that. We can get up, enjoy our morning routine in our PJ’s or other comfy clothes, and get dressed when we wish. 

I work from home and am not even close to retiring, but I can wear what I like when in the office because I never have to leave the house. It’s a good/bad thing. I don’t want to dress like a slob, but it sure is comfy, and who’s going to see me, anyway?

By the way, if you click on a link and then make a purchase, I may earn a small commission at no additional cost to you. Thank you!

If we get into the habit of a super casual type of dress, when it’s time to head out the door for a social engagement, to dinner, church, even to go shopping, we might feel paralyzed when gazing into a closet that is full of clothes we’re not sure what to do with.

So…here are some tips for those of you who can relate to this uncertainty. How to put an outfit together is not an exact science, as there are personal factors that play into our choices:

Actually, there is quite a bit more that goes into which hangers to pull out of the closet than the clothes that hang on them, as you can see from the suggested reading above.

If you’re looking for a way to take all of this good information and see it presented in a simple, fun, and lasting way, check out my email series course, The Fashion Cure. Just click on the image below!

Over 50? How to Put an Outfit Together

how to put an outfit together - the basics of fashion for women over 50 and over 60

THE BASICS of fashion and style in midlife

Let’s talk about some of the basic how-to’s and suggestions for your wardrobe, and then we’ll get to the specifics.

1 | Make sure your clothes fit properly.

You don’t have to spend hundreds of dollars on an article of clothing to get a good fit. But sometimes it’s a bit of trial and error.

If you’ve read the post above on understanding your body shape, you’ll have a better idea of how to approach the task of finding good-fitting clothing.

Avoid clothes that are too baggy. If you’re swimming in your tops and bottoms you aren’t creating a look of confidence and style, inside or out.

2 | Bring some bright color into the wardrobe.

Our skin and hair changes as we age. There’s an understatement. 🙂 We don’t have the fresh vibrancy of youth on our side any longer, even though we take care of our skin by making wise choices. It is still aging skin.

You can determine which colors will look best on you by checking the veins on your forearm:

  • If they look blue or purple, you’re cool-toned
  • If they’re green or have a yellow cast, you’re warm-toned.

So, the ‘cool girls’ will most likely look better in, and naturally gravitate to, cool colors like white, black, gray, navy, royal blue, jade green, and other colors that remind you of water, sea, and sky. Bright shades of pink and rose also compliment a cool complexion. You probably choose silver more often in jewelry.

Those of us who are in the ‘warm club’ usually look best in earth tones like burnt orange, dark leafy green, taupe, camel, sunny yellow, etc. Gold jewelry usually looks best on us, although I wear silver and gold both, and am happy with the overall look.

3 | Fabrics that flow are your friend

Think about soft cotton, cashmere, knit blends that drape but don’t cling…those are the fabrics you want to gravitate to.

These are three of my favorite tops. The black one on the left and the sleeveless top in the middle are from Covered Perfectly, the micro-modal fabric has an incredible feel, and is never clingy. Read more about my experience, and why I recommend purchasing from this online source. (Yes…I went from an auburn hair color to my natural gray, and I love it!)

The other knit top has been favorites of mine for quite awhile. The knit fabric holds it’s shape, drapes well and the neutral shades are very versatile.

With jeans and slacks, a fabric that has a little bit of stretch to it can actually help us to look younger, and slimmer, if paired with the proper top layers.

I have some skinny jeans, leggings (a new look for me), and pants that have just enough stretch to be fitted but not tight.

To look well put-together, avoid baggy, floppy pants unless you are going for a wide-leg look from a fashion standpoint. My opinion on that trend? Unless you have a great figure from top to bottom, opt out of the wide leg fashion statement if you’re a woman over 50.

4 | Don’t shop like an old lady

I don’t want to offend, but seriously. If you really want to put together a look that says, “I’m confident and look great!”, you probably don’t want to shop in the Mature Women department. The goal for most of us is not to dress old!

Elastic waist pants have their place, as do collared, short-sleeved shirts with slits on the side (for extra expansion), but those choices won’t take you in the fashion direction you want to go if you really want to spiff up your wardrobe.

Your clothing choices are only as versatile as where you shop.

5 | Don’t forget about your feet

We have so many choices now in footwear, ladies, almost all of us can find shoes that look good AND feel good.

If your closet includes one pair each of these, modified for your locale, you’ll be in good shape:

  • walking/workout shoes
  • casual flats
  • sandals/mules
  • classic heels
  • fashion booties
  • weather appropriate boots

THE SPECIFICS: what’s in your closet?

how women over 50 can put an outfit together and feel great

I know. We need more than some great footwear in our wardrobe. As women over 50 and over 60, here are some suggested separates that will help you answer the question of how to put an outfit together.

This is not meant to be all-inclusive, but it’s a good foundation. You’ll probably have some other tops, statement pieces and other items you love to have in the closet.

Where you choose to purchase these wardrobe staples, as well as your color choices in the tops and other separates, are a personal decision based on the specifics discussed above:

  • Well-fitting ankle length pants in a dark color
  • Dark denim jeans, straight leg or boot cut
  • Leggings (or similar) in black, navy or dark denim
  • Two or three tank tops or short sleeve tops for layering
  • Cardigans with long or 3/4 length sleeves. Hip length is very versatile, and longer length (which I love!) is great for straight leg jeans or pants
  • Pullover sweater(s) in neutral for layering or to wear on their own
  • Fitted jacket (not too tight) in black or navy, consider ivory or cream also to give you more flexibility.
  • Classic white button-down shirt
  • Pencil skirt that comes to the knee or just a bit shorter, black
  • Little black dress (LBD) to dress up or down as needed
  • Dress(es) – if that suits your style. These styles flatter women in midlife: a wrap dress with long or 3/4 length sleeves, tied at the side; a sleeveless sheath dress to wear with a snug fitting cardigan or jacket, a dress that is fitted at the top and flares out slightly starting at the waist

THE STYLE: put your look together with these 6 Simple Tips

how to put an outfit together and love the results

So beyond staring into the closet and noticing that yes, you do have some or many of these suggested wardrobe staples…what comes next?? Because they’re not going to jump out of the closet and arrange themselves on your bed in beautifully coordinated outfits. (How cool would it be if they did, though?!)

BTW, if you love the outfit in the image above, you’ll find shopping info. in this post: https://inspiremystyle.com/2018/05/05/casual-styles-for-women-simple-stylish-classic-fun/

This is my simple 6-step system that answers the question of how to put an outfit together as a woman over 50.

1 | think about a) what you are dressing for (the store? church? a party?) and b) any weather implications?

2 | decide how you’re feeling about your outfit, and what is more important to you. Is it comfort? warmth? turning heads when you walk into the room? Do you feel like being colorful today? Classic? Playful? Somber? Youthful? Your overall feeling will help you narrow down the individual pieces.

3 | Slacks, Jeans, Skirt or Dress? Make the decision.

4 | Add two layers to the choice made in #3. It could be a long tank top and cardigan sweater to wear over a pencil skirt. Or, a short sleeve top and extra long cardigan to wear with your dark jeans. Or, the white button down shirt topped with a pullover sweater. Get the idea?

5 | Select the footwear and accessory pieces. Do you have a particular handbag for this outfit? A pretty scarf? A hat? Make these selections, then finish off with…

6 | The jewelry, if that’s part of your personal style. If you keep your selections to three pieces or less, you’re good.

These six suggestions are a basic foundation for putting an outfit together, and they work well for a woman over 50 or over 60. Are they meant to be ‘rules’? Of course not.

Bottom line, you’re big girls and can decide what to wear. But if you’re looking for a little bit of guidance in the fashion arena, these tips will steer you in the right direction.

Grab your printable from the Free Resource Library, so you’ll always know how to put an outfit together:

Examples of casual, coordinated outfits for women over 50

outfits from  Chicos for women over 50

Sometimes it’s helpful to see images of outfits that are well coordinated and complete. It helps to spur our creativity, and can also help us make clothing decisions.

These photos are from Chicos.com. I like them for several reasons:

  • the model is over 50
  • the selections are going to appeal to many women in midlife
  • the looks are layered and show how to combine separates
  • the website offers a ‘shop the look’ for each outfit for ease of purchase

These looks may not be your cup of tea, and that’s cool. We’re all unique and have our own preferences. But you might find something in these that is helpful.

For example, I’m not a fan at all of the long blazer on the left because of the fabric. Remove the blazer and I love the outfit. Or, change it out to plain navy and I’m there.

Here is another look I put together that is simple and classic but still updated and stylish:

Ponte Slim Pants | Open Draped Knit Shawl Cardigan | Ponte Top | Mixed Print Necklace | Animal Print Drop Earrings | Animal Print Stretch Bracelet | Black Mules | Triple Compartment Satchel

This outfit was curated from White House Black Market, a sister company of Chicos. It’s another classic look with just enough pattern and texture to make a style statement.

how to put an outfit together from White House Black Market

Knowing how to pull together an outfit, a look, is something that some women just know how to do…they have the knack for it. If you’re not one of those women, use these basic tips and suggestions, and you’ll be able to put an outfit together and feel confident. And, I’ll bet you’ll look fabulous, too!

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6 steps to help you put a stylish outfit together as a woman over 50

8 thoughts on “Over 50? How to Put an Outfit Together with Confidence”

  1. Two of the biggest fashion struggles I have are 1) the desire to purchase clothes online, but in reality needing to try things on, and 2) buying clothes that fit wonderfully until I wash them once (even if I follow the care instructions precisely). I agree with you that fit is the most important thing. I have long legs and have at times kept clothes that I otherwise like, but that are a bit too short. I always regret that. I have also fallen in the baggy or too clingy trap. Draping is a perfect description of what I’m looking for. Thanks for the great post.

    1. Hi Christie, I agree that while buying clothes online is convenient there is always the fit question. I always make sure the return policy is reasonable! But you can find some great buys shopping online. It’s always a challenge! Thanks, as always, for taking the time to read and comment. I really appreciate it!

  2. Though I have most of these staples in my wardrobe, I really appreciated your tips on how to put them together. My biggest challenge ahead, when we move to a small city, and will be mostly working on our house, is how to dress down for the more casual lifestyle. I like dressing up and wearing pretty clothes, but it really won’t be suitable, when working on a house. Oh well, I guess I’ll have to save the dressier attire for when we go to the Netherlands in February. Sharing to FB.

    1. Hi Christina, well, you could look at it this way…it will make those pretty outfits even more special because you won’t be wearing them often, at least for the time being! Keep those jeans and t-shirts handy for work days. 🙂 Thanks for sharing!

  3. Candi, This article as very informative. I have a difficult time because I’m always dressier than others. I grew up this way. I am most comfortable dressed up more. I only wear skirts. As people get to know me they realize this is just my style. Always has been!! I’ve had to learn to just be me!! There are no do overs in this life!! I just want to comment about on-line shopping. As a disabled women that is physically unable to go shopping I’m very thankful for on-line shopping. Take your measurements and assume you will need to exchange or return items. That’s just a part of on-line shopping!! When you find a great place on-line to shop then do alot of your business with them!! I just praise the LORD for on-line shopping. I do go to SAS store to buy shoes. I also usually buy handbags in person but I have ordered a leather purse on-line and it’s one of my favorites!!

    1. Hi Natalie, I agree that online shopping is awesome, in so many ways! And you are absolutely correct in that you have to prepare for the inevitable return here and there, but it is still worth the convenience. Thanks so much for sharing.

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