Monthly Makeover: How to Make an Outfit Better

I'm taking a basic look that I see often in my retirement community, and giving it 7 different upgrades.

My goal was to show a look and change out just one or two things that could really give it some personality. It’s not much different than how I showcased 6 different styles of jeans all with the same top half and boots.

I always think that comparisons can be very powerful in this way.

I'm sharing 5 of the ideas here, and then head over to my blog to see 2 more.

The Basic OutfitThere is nothing wrong with this outfit. It fits, the proportions are considered golden and are modest. For my personality, it’s a tad muted and dark, but I know that some women prefer that, especially in the winter months.

In fact, I love all of the pieces since they are in my closet and have been for a while.

Jeans: Old Navy-Boyfriend Jean~~ Sweater: So old there is no label~~ Boots: Jambu from many years ago

Now let’s break down this basic look.

1-Boyfriend jeans. Not just because the jean silhouettes are changing, but I see baggier jeans on older women as a rule. These exact jeans are still available in select sizes, yet I feel like Old Navy, always has an amazing selection of denim that spans many sizes, silhouettes, and colors of washes.

2-Black, crew neck sweater. It’s something that is considered classic and will go with everything. That’s why we call it a basic piece, right? The thing is if we only wear basic items, then we can look a little basic ourselves. And while that is some women’s preference, I truly think we all have such amazing personalities that we should consider showcasing sass in our appearance too.

3-Black ankle boots. Again, another basic that bookends the sweater. Don’t get me wrong, I love these booties and wear them a lot.

4-Delicate necklace. And earrings. Can you even see my earrings? Probably not.

As I always say, accessories can really add to a look. These delicate jewelry pieces aren’t overpowering and aren’t heavy to wear. Yet proportion-wise it doesn’t fit in with the big expanse of the black sweater and the earrings are hidden in my hair.

How to Make an Outfit Better

Taking this same basic outfit, I’ve come up with 7 thoughts on how to make it have more personality. I’ll break it down and start with layering.

When I think of layering, I always like to remember there are TWO ways to layer.

Over and under.

Say it with me. “Over and under.” Now repeat that sentence every time you think about putting an outfit together. Because almost every piece of your wardrobe can be layered both over and under something else.

In fact, each of my examples could be a post on its own. There are tons of different options with colors, shapes, and sizes that would work for my idea of how to make an outfit better.

But I tried to pare it down to just the 7 that I’m showing today.

Bow-tie blouse: The Limited

Layer Under a Sweater

Starting with the idea that I can layer under this sweater, I grabbed this bow-tie blouse. Any blouse would work, but I loved the fact that the bow could be tied in the front and take up some of that black real estate in the front of my body.

I also left the shirttails hanging out under the sweater to give it more sass. You might say that it skews the proportions so they aren’t as golden (1/3 to 2/3), but I still like it.

Insider tip: If you are always hot, you could opt for a sleeveless blouse.

Layering Over a Sweater

As I said above, there are endless possibilities just with layering under this crew neck, black sweater. Things like:


2-Peplum top where you just see the bottom peplum under the sweater (like I showed here when I said layer over it)

3-Heck, you could wear any longer top to hang out under the sweater, not just a peplum

4-Any collared shirt

5-Dickey or halftee if you don’t want a lot of layers

I’m showing 2 options for layering over this sweater. Again, this category could be a post on its own with all of my ideas that I will share below.

I narrowed it down to two options for my third piece- a vest and the other one has sleeves. Both would work. And both would be fabulous ways how to make an outfit better.

Vest: preloved from a friend

I also wanted to show both a longer third piece as well as a shorter third piece with these layered looks.

You could layer any length of vest or sleeved item for this idea.

1-Cropped which would even be shorter than the sweater. Leaving the sweater to hang lower adds interest just like I did with the bow-tie blouse

2-Same length as the sweater

3-Mid-thigh length (which is what I would consider this ivory vest)


And I wore a blazer, but this would also be great with a cardigan, jacket, shacket, coat, or even a button-down blouse. You can incorporate all of the different lengths too.

Insider tip: Even a faux/leather black jacket would add some interest to this basic outfit because you would be incorporating a different texture into the mix.

Jacket: Seen here when I added color embroidery to it

Boots: Embassy London-won in a giveaway


I’m a huge proponent that your footwear can be a fabulous part of any look. With the internet and new brands popping up, there are plenty of companies that make comfortable shoes that look cute too. Even if you have foot issues.

I think just the addition of a totally different color with your shoes, creates a whimsical and modern look. On top of that combat boots are beneficial for older women. Why? Because first off they are contemporary and make you look like you’re “with it”. And secondly, most of them are flat so women who can’t wear heels can indulge.

Necklace: Just Be Youtiful~~Earrings: Mariposa Skies ~~Bracelet: Local boutique

Bigger Accessories

The basic outfit did have accessories, but it goes to show that not all accessories are created equal. It all depends on the outfit, right?

With this solid sweater that creates a huge expanse of black in the front of my body, it’s nicer to have a bigger or longer necklace to make more of an appearance.

The necklace is a fun “girl” necklace from my favorite local boutique Just Be Youtiful. She only has them in her store, but you can certainly reach out to the owner, Kym, and see if she has more and would ship them to you.

The earrings are leather which makes them lightweight. The lighter color allows them to contrast against my hair. That’s the thing. As our hair changes color, we need to reevaluate what color earrings we are wearing.

Insider tip: Remember, many earrings can be DIYed with paint. In fact, I’ve used fingernail polish in the past.

How to make an outfit better: the black sweater made more interesting

Make sure to he ad over to my artic le to see the 6th and 7th options of changing up this basic outfit.

The author may collect a small share of sales from the links on this page.

Jodie Filogomo
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