I Finally Dress My Age | From Frumpy to Chic | Outfit Makeovers!

It’s the moment you all have been waiting for. 🙂 I finally grow up and dress my age. No more ripped jeans or sassy shoes.

Just kidding.

You know that will never happen.

Here’s my philosophy on “dressing our age.” It’s different for every woman. The goal shouldn’t be to dress younger or older. The goal should be to dress in a way that is flattering, modern, and sophisticated. Once you check all of those boxes, age becomes irrelevant.

Today, I take frumpy, aging outfits marketed at women over 50 from stores many of us know and love, like Chico’s and Talbots and even Loft, and give them makeovers so that they look fresh and contemporary!

You do not have to start over with all new clothes to get a fresh and contemporary look. Many of the existing pieces in your wardrobe can work if you style them in a modern way! I show you how it’s done in today’s video!

In this Before picture, I combine several elements that are common in outfits that look too mature. And most of it comes down to the accessories. The shoes are unflattering and not at all modern. the bag is utilitarian but not stylish, the necklace is clunky and out of date, and I’m wearing the eyelash textured sweater out, as a tunic, with jeggings that feature no back pockets. These are not real jeans. 🙂 I also styled my hair in an unflattering way.

In the After pic, I ditched the accessories. Then, I added a pair of modern but still comfortable loafers in wine velvet from Zara, a cool clutch from Target, and a great pair of drop earrings from Dean Davidson. I did a front tuck of the same Chico’s sweater into my Mott & Bow Slim Boyfriend jeans, and the effect is cool and contemporary while still being casual and comfortable.

In this Before pic, I am wearing a sequined Chico’s jacket over a matching foil print tee, boxy unflattering beige capris, metallic comfort sandals, and the same clunky necklace and bag. My hair is artfully styled into a frumpy bun.

In this After pic, I fix the bun (a little), and swap out the dated foil print tee and unflattering capris for a simple white tee from H&M and my Mott & Bow jeans. I switch the bag for a clutch (although any contemporary bag will do) and the sandals for a pair of pumps. You could do any flat with this as well, but I loved the modern pop of color here.

I have two Before pictures with this same slightly boxy but neutral Chico’s jacket. Here, it is paired with cropped Liverpool jeans with a floral trim that is dated, a quilted floral bag, and the same sandals. Too much going on, and none of it modern.

In this Before look, I’m wearing the same Chico’s jacket with a matching patterned top that is dated and also at an unflattering length. It is paired with the boxy beige capris and the same unstylish loafers. Can this jacket be saved?

In this After outfit, I paired the same jacket with the H&M tee and Mott & Bow jeans. I added neutral accessories (both from Target, by the way) and easy instant outfit transformation.

This is what I call a Garanimals look, because it is overly coordinated and there is nowhere for the eye to rest. It combines a patterned cardigan with a matching shell in a solid (a common, aging combination), and then I’ve added the boxy beige capris, the clunky sandals, and a statement necklace that echoes the colors of the outfit.

Just switching the patterned cardigan for a solid one and losing the necklace makes a big difference, and while this is not exactly an After look, it is definitely an improvement!

And now for the After shot. I lost the twinset look, which is dated and a little mature looking, and turned the cardigan into a sweater by buttoning it up. This cardigan is actually a little too snug to be worn this way, but this technique is a great way to wear your classic cardigans that seem a little out of date. I’ve swapped out the pants for the jeans and added neutral shoes.

This After, while still not my favorite look, is a definite improvement using the patterned cardigan. Just pair statement pieces like this with modern basics for a fresher look.

This shapeless and brightly patterned dress from Clara Sun Woo looks like a housedress, especially when paired with the comfort sandals and blingy blue necklace.

I added shape to the dress with the addition of a little white leather bomber jacket from St. John Sport, and suddenly the dress is less tentlike. My silver Seychelles mules complete the look.

I hope that these outfit transformations gave you ideas for new ways to wear the pieces in your existing wardrobe. Start with what you have, mix in a few modern wardrobe essentials, and you’ll have easy and elegant outfits for days!