How to Wear One Outfit Two Ways

Hi friends! The time has come to cue up, “We Wish You a Merry Christmas” because the finish line is in sight. Maybe you’re traveling this week and trying to figure out what to pack. Let’s look at how to wear one outfit two ways.

This is one of my latest outfits from Chico’s. In the last year I’ve joined my mom and become quite a fan of Chico’s. She wears Chico’s almost exclusively. It’s funny, I wore it years ago, and then for the longest time I just felt like it was too old for my personal style. They got a new designer this year, and she’s brought in a bit of a younger style in many pieces. I’d say they’re still known for bright colors, and prints along with a certain Mrs. Roper style, but they also have some really good pieces that are little more understated.

how to wear one outfit two ways
JEANS || SWEATER/TOP || VEST || SNEAKERS (use code COAST10 for 10% off)

This outfit is a good example of the new style. These jeans are from the Define Me Denim line and they fit me really well. Chico’s jeans used to be too long in the stride for me, but I really like these, and they have a slightly lower waist compared to all the high rise jeans most retailers are carrying. The denim is nice and soft with just the right amount of stretch that holds it shape while allowing some give. You should give them a try if you need jeans. I also like the straight leg styling. I cuffed them for a casual style with sneakers, but you’ll see in a minute how they look down with a bootie.

how to wear one outfit two ways
JEANS || SWEATER/TOP || VEST || SNEAKERS (use code COAST10 for 10% off) || BAG

I really like this sweater shirt combo, that is actually one piece. That makes layering so easy and you don’t have to fiddle with getting the layers to play nice. The length is nice too. You could easily throw this on with leggings if you wanted.

The vest is super cute. I love a vest and when it’s cool but not freezing they are a nice alternative to a coat.

The bag is from Chico’s too. They’ve been having some really fun accessories and shoes in the past few months. This bag comes with a slightly smaller inner bag to actually hold all your things and has a zipper. It also come with a longer strap for your shoulder or crossbody.

You can see I changed shoes and gave it a more polished look. The jeans lend themself to either way, and you could just as easily pair a mule or even heel with them. You could wear this pair of jeans on a trip and style them a different way each day.


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  1. December 19, 2022 / 5:04 am

    Chico’s has great quality and great sales. I just stay away from the Mrs. Roper stuff! Lol! I think they have some great wardrobe staples. I am in love with my faux leather pants in black and cherry brunette and my black silk blouse. Thanks for highlighting their stuff!

  2. December 19, 2022 / 7:32 am

    Love your layers! Both are really cute! Shoes can make a differece!

  3. Hope
    December 19, 2022 / 11:45 am

    Hi Lisa, I love both looks! What size are you in the jeans? I get confused by the Chico’s sizing. I am same height and size as you. Do you find their regular lengths work for you? I try to use the states inseam lengths but sometimes those aren’t always accurate, or the way the pant fits makes a difference.

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Trinny London