7 ways to wear 1 dress! {outfit ideas by Lisa Leonard}

I had so much fun putting this post together. It could alternately be titled “me, me, me” because there are SO many photos of me. But then, this is my blog–so hopefully you’ll bear with me!

I took my favorite black dress and styled it 7 different ways.

Here’s the dress. I found it at one of my favorite thrift stores for $4. If I knew how much I was going to love this dress, I would have happily paid $100 for it. It’s turned into one of my go-to basics. I think it’s from the 90’s and I couldn’t find anything quite like it online. It’s really the skirt that makes this dress so great. I found this skirt at target–paired with a great black tank or tee and any of these looks would work! Black is a great basic–don’t you think?

For look 1. I styled the dress with a cozy brown sweater, a floral scarf and bronze boots that I thrifted in Texas last weekend. Score! Sweater, White Stuff {British Brand}. Floral scarf, Forever 21. Boots, Thrifted. Happiness Bracelet, My shop.

Look 2 is fun because it mixes stripes and leopard print. Easy and sweet! Sweater, Downeast basics. Leopard print heels, Target. Fossil Necklace, My shop.

Look 3 is a little preppy, don’t you think? Tie a white t-shirt at the waste and it creates a totally different look. I look for white button ups in the men’s section at thrift stores. A men’s small is like a women’s medium. Awesome! White button-up, thrifted. Denim jacket, Old Navy. Red wedges, Payless. Bangles, Thrifted. From Any Angle Necklace, My shop.


Look 4 is the sort of thing I throw on when it’s a crazy morning because it’s cozy and comfortable–but still put together. Striped wool sweater, BB Dakota. Brown booties, Steve Madden. Mustard scarf, Fair trade. I Love you bracelet, our Heartfelt collection–available here.

For look 5, how about a bright, bulky sweater to add some warmth and fun? I found this sweater on sale for $8–insane! Sweater, Target. Striped scarf, Target. Black wedges, Payless. I love you bracelet, from our Heartfelt collection–available here.

I wore Look 6 quite a bit last summer. It’s such an easy outfit. Safari vest, Old Navy. Nude wedges, Payless. Bangles, thrifted. Gold barrel necklace, Coming soon to my shop!

This last look is something I would wear for a date night. Denim jacket, Gap. Bib necklace, Target. Leopard clutch, Forever 21. Black booties, Seven for all Mankind {a Christmas gift from my mother in law–thanks Mom!}

And that’s it, friends! A whole weeks’ worth of outfits built around one dress. I love it!

Would you like to see more posts on a single piece used multiple ways? Or if you have other ideas for WIW posts–leave them in the comments. I’d love to hear!


  1. I would love for you to do a post with all your different ways to wear a scarf! I have yet to master the scarf and yours look so effortless! Tutorial please!,,,,

  2. LOVE this – you have given me so much fodder for fashion inspiration! I was just looking at a black tank dress today and wondering how I could wear it- Ha! Perfect. 🙂

  3. Okay, I know this is just plain weird, but that was my dress–I am an adherent of if you don’t wear it, adios….glad you are liking it!!!!

  4. I found the cutest navy blue Michael Kors tank dress on the clearance rack today and couldn’t help but think of this post!! Thanks for the inspiration, I’m going to accessorize the heck out of this sucker! 😉

  5. Wonderful post! You have given me inspiration! I also love your hair style. I have curly hair. May I ask how you style it? Thank you 🙂

  6. AWESOME! Please do more of these posts, I love the inspiration I get from seeing the way you pull your looks together! LOVE!!

  7. What a great idea, to copy the look with a long skirt & tank. Putting this into action.

    Do you have any comfort issues with your Payless choices? I’m not above buying Payless, but find the fit is really odd (usually too big) and just not comfortable enough — as a mom, life is too busy for painful shoes! (But I love those red wedges!) 🙂

  8. YES! Please do more posts like this! I love how you mixed in unexpected colors, shoes & textures, like the red wedges, boots & booties. Love the fact you started with something so basic as a black dress. Could be black skinny jeans and a black tank, so anyone could make these looks work – so versitile! And SO inspirational! My fav is the last one…classic. I’d love to see how you would dress up blue jeans and a white t-shirt 7 ways! I’d love to know what color of purse you use on a daily basis!! Do you use a neutral color, and if so, what neutral color? or do you “match” it to your outfit? 🙂

    1. I love this for packing light too. I often wear the same thing over and over on a trip anyway. I think I should plan around it bring more accessories. xo

  9. absolutely! I’d LOVE to see more posts just like this – I’m all about wearing favorites and this is awesome for travel and busy mornings! thanks!

  10. I love your style! I am copying the two looks with the denim jacket this spring. I never know when to wear mine!

  11. This is a GREAT post. I LOVE seeing you make several outfits from on staple piece. Gets me thinking outside of the box. I would LOVE to see more posts like this. You rock!

  12. So fun! Love this post! I love that you paid 4 bucks and it is so versatile. Very cool! My fav is number 3, paired with the white collared top and denim and red shoes.

  13. my favorite is the “preppy” look. great find with the dress. i’m not sure everyone could successfully pull off so many looks like you do.
    my husband & i recently took a vacation for our 20th anniversary & hit the pacific coast hwy and spent some time in SLO. beautiful place & the farmers market was awesome even if it was january 😉

  14. I would love to see more posts like this one! It was so fun to see you transform simple pieces with different accesories. It motivated me to take a closer look at my closet and create some new looks! Thank you!

  15. I really enjoyed this weeks wwiw. I would like to see you do that more often, you gave me a lot of inspiration. Lisa, I love how you take risks with your fashions. You go girl!!

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