Most days I leave the house feeling like I nailed my outfit. I am looking HOT. I strut my way through Costco, along my son’s soccer game sidelines, and in the carpool lane. And because I look SO. GOOD. I document every outfit with a daily selfie as a way of figuring out what I do and don’t like.
Y’all, cameras don’t lie. When I look back at my pictures, sometimes it’s like a catalogue of shame. What was I thinking? Why did I wear that? WHY? And why did I let others see me in that? Ok, so some of them aren’t that bad, but some of them are. Seriously. The great thing about life is we grow and learn. Hopefully. My style is an evolution, and I am always learning and refining what I like, what looks best on me, and little tweaks to take my outfit from good to WOW. In the updated outfits, I’m still wearing the same basic elements, but by choosing different versions, I made big improvements on my outfits.
Even as I was pulling together this post, my inner perfectionist was fixing some of the new outfits, so you might see these again next year. The silver lining is I’m learning and improving every day, so there is a purpose to it all.
You loved the fall edition of what I wore when I wore it better, so I’m doing a winter edition to show you how I took an old look and improved it! Some of them only required small changes, some required bigger adjustments, so let’s take a look at what I wore when I wore it better this winter.
Have you worn an outfit better?
So the original outfit wasn’t terrible, but it wasn’t flattering to my figure. I love the sweater, but the skinny jeans and boots aren’t right for me. I have always loved tailored clothes, but being this fitted from top to bottoms accentuates my pear shaped figure and doesn’t give me the balance I need. I love a black moto jacket, and wear mine all the time, but this particular one didn’t fit me right. It was too small and too cropped. It’s not labeled petite, but it fit my very petite friend perfectly. I remember when I bought that oval necklace I thought I was being so bold and so crazy, and now it’s too meh for me. I need different shapes in my jewelry. Triangles, diamond patterns or anything that could do serious bodily harm.Â
Wearing this very fitted sweater with bootcut jeans and a properly fitting jacket make me look more balanced. Wearing stabby jewelry is more honest about who I am, and a bolder statement necklace stands up to the bold color blocking better. The smaller necklace gets lost.
I would also like it with the black jeans, but I was in the mood for destroyed jeans that day.
Sweater similar here. Jeans (I made them bootcut). Necklace similar here and here. Boots similar here. Jacket similar here.Â
This one is also not terrible, but it’s not right for me. First, I don’t wear polka dots. They are too sweet and light for me. I’m a pretty serious, intense person, and wearing polka dots makes me look even more serious. Second, the skinny jeans aren’t right for me. And these are worse than skinnies in some ways. They are more straight-leg, and too long, so they are bunching around my calves and ankles. Wearing the piped button up and the brooch still adds a layer of interest while still being true to who I am, a bold, stunning woman. Linear lines tell a true story, polka dots mislead. Adding the brooch to the collar is a great way to accessorize when you don’t want a necklace.Â
Sweater similar here. Blouse nearly identical here.  Jeans. Boots similar here. Jacket similar here. Brooch here.
Ok, now this one is really bad. It’s way, way, way too much. This was my Awesome phase. I was trying to be too awesome in all my outfits. The sweater with the scarf with the jacket with the hardware on the jacket with the hardware on the pants with…Let’s go one at a time. As I mentioned above, this jacket is too small and cropped for me, and compared to the length of the sweater, the cropped length of the jacket looks even more dramatic. Those circular rivets on the pants draw extra attention to my hips, and they are round, like giant polka dots up my thighs. That is not a spot I want to accessorize. I was specifically going for edgy when I bought those jeans, and I missed the mark.
The scarf is an additional color, additional bulk with the band collar of the jacket, additional sheen, and additional fringe. The cable sweater texture adds to the busyness. On top of it all, I tried to front tuck the sweater. The whole thing is too. much. Way too much. I’m not sure where to look first.
In the improved outfit I have a jacket that fits me perfectly. I’m wearing bootcut jeans to balance my proportions, and there is no extra hardware on my hips. I still brought in the turquoise with a small statement necklace and stud earrings that I picked up on our trip to Mexico. The sheen on my boots ties into the sheen of my jacket and the jewelry, bookending my outfit. There is way less going on in this outfit, but I still get the colors and elements I was after. The focus is up on the top half of my body, where I want it, and the eye can rest.Â
Sweater similar here. Jeans. Boots similar here. Jacket similar here. Earrings similar here.
The outfit I’m improving on is from last month. That leather patch pocket sweater made me go all heart eyes when I saw it. I wore it last winter and loved it, but it is meant to be worn with skinny jeans, not boot cut. It made me feel frumpy and boxy. The shiny pockets also draw attention to my hips. If you saw the first installment of my closet purge, you know I let go of this sweater. Changing to the raglan leather sweater that skims my body instead of obscuring it is a huge improvement. It helps balance my proportions without losing the leather details that I love.Â
Sweater similar here, here, here,and here. Jeans (I made them bootcut). Boots similar here. Necklace dupe here.
This is another awful one. Where to begin? Let’s start with the cowl neck. What does that suggest to you? It suggests soft and loose. I’m not soft or loose. I’m firm and structured. I love the texture of the sweater, especially the diamond pattern, but not the fit. Or the sequin details lighting up the diamond pattern that happens to go right across my bust. Those pants are doing me zero favors. Not only are they skinnies, they were also a size too small, and I look like I’m being squeezed right out of them, as you can probably tell. Even though I have long legs, the ankle boots cut me off in an unflattering place, giving me the appearance of thick ankles.Â
The new outfit creates a much better silhouette that balances my shape by keeping it tailored at the top and adding some width at the bottom. The ribbed texture and the button details on the sweater take a basic top and make it special. I chose a shiny black necklace so it wouldn’t compete with the buttons. I’ve searched high and low for cobalt bootcut jeans and finally found trousers instead. For now they work, but I would love to find them in denim, so if you see any, holla!
Sweater similar here. Pants also here. Boots similar here. Jacket similar here.Â
The change to this outfit was simple, but significant. For whatever reason, I decided to try rolling some straight-leg jeans in all their bunchy glory and letting them sit on top of my boots. Ick, and no. The length of this sweater is also not flattering on me. For the new outfit I wore bootcut jeans, and did a little front tuck with the sweater, and I’m undecided on how I feel about that. I also went with no necklace because the sweater is so textured it was enough excitement for me. It was also the day I took all 6 of my kids to an all-day dance competition for my girls because my husband was stranded in London by the Beast from the East.
Side note: I’ve been growing out my hair, and this poofy mushroom stage is making my crazy. Ringo Starr called, and he wants his hair back.Â
The original outfit was only two months ago. I’m not exactly sure what happened, but I remember being in a hurry to get out the door to church on Christmas Eve. For some reason I wore a black skirt, black patterned tights and shiny black heels with a navy and red plaid top. I have no qualms about mixing navy and black, but the black + navy + super textured necklace + patterned tights + shiny heels was too much. This time I paired the top with a navy skirt, nude hose (I know some people think that’s an unfashionable thing to do, but I cannot go bare legged in the winter. Any added warmth is a good thing, if you ask me, and it makes my legs look better), and navy snake skin heels. The snake skin is a subtle pattern that adds a little texture without competing with the pattern in the blouse. Shirt similar here. Skirt similar here. Shoes similar here.Â
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And finally, here is my latest bold manicure.Â
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