Black & White Striped Dress Styled Two Ways

Well, hello there. Welcome back! I’m on a roll with the outfits lately. Today I’m styling a black and white striped dress outfit for fall — two of them, actually!

Black and White Striped Dress Outfit for Fall

I saw this black and white striped shift dress at Old Navy and immediately began thinking of all the fun ways to style it. It’s such a versatile piece. First I paired it with black suede ankle boots and then with bright pink suede flats. It was 75º outside the day we took these pictures so I went bare-legged (albeit with the help of my favorite self tanner), but when it gets colder, I’ll add tights.

This is a casual dress so I wanted to keep the shoes on the more casual side — flats seem like the best bet, although these ankle boots do have a low wedge heel. For winter, I can pair it with grey suede knee-high boots or flat black over-the-knee boots. And wouldn’t it be gorgeous with burgundy suede booties? So many possibilities!

I love these Lucky Brand booties. They are super comfortable, and the style is classic but modern. They go as well with skinny jeans as they do with skirts and dresses. They also come in a pretty honey suede, AND they are currently 40% off!!!

Styling the Lucky Brand Yezzah Wedge Bootie with a black and white striped shift dress for fall

For this look, I kept the accessories simple with a gold pendant necklace and oversized faux diamond studs. I added a stack of Alex and Ani bangles to one wrist, and I wore a cuff bracelet with my watch on the other.

The purpose of the pendant is to draw the eye down and in towards my waist. The dress doesn’t have much of a waist; I’d prefer the dress if it had a bit more shape to it, so the pendant helps to create that visual effect. It would be even more effective if it were a little bit longer.

Black and White Striped Dress Outfit for Fall with Ankle Boots

For fun, I decided to tie a jean jacket around my waist. As I said, it was 75 degrees so I really didn’t need to wear an extra layer, but I like the effect. The shift style dress isn’t always the most flattering since it doesn’t have a lot of shape through the waist, so one way to add some curves is to tie a jacket or shirt around your waist. Plus, when it gets colder, it will be nice to have the option of a layer.

How to Wear a Black and White Striped Dress Outfit for Fall: with black ankle boots, denim jacket, and burgundy bucket bag

I carried my burgundy suede Stella & Dot Covet Sunday Bag because I like the contrast of the burgundy against the black and white for fall.

How to Wear a Black and White Striped Dress Outfit for Fall: with a denim jacket and burgundy bucket bag

How to Wear a Black and White Striped Dress Outfit for Fall: with black ankle boots and a burgundy bucket bag

This dress is only $22, and I’m wearing a medium in the regular size. It’s a nice thick, heavy knit made of 100% cotton, and it’s machine washable. It says it hits at the knee, but as you can see, it’s quite a bit shorter than that. I’m only 5’5″ so take that into consideration. It also comes in tall and petite sizes. The 3/4 length sleeves are great for showing off your bracelets.

How to Wear a Black and White Striped Dress Outfit for Fall: with a denim jacket and burgundy bucket bag

For a more casual whimsical look, I also tried the dress with my pink suede flats. I love these with this dress. The overall look is easy and comfortable but a little bit unexpected.

How to Wear a Black and White Striped Dress for Fall: with pink suede flats and teal crossbody bag

These shoes are also 40% off!!! I didn’t even realize that until I went to write this post. I absolutely adore these flats. I have them in both pink suede and black leather. They’re comfortable and super cute. The spike detail on the back adds a touch of edgy to these otherwise classic pointy toe flats.

I thought the teal bag added a fun dimension to this outfit. It coordinates nicely with the bright pink shoes without being matchy-matchy.

How to Wear a Black and White Striped Dress for Fall: with pink suede flats and teal crossbody bag

Either way, this shift dress is a great staple to have in your closet. I don’t wear many casual dresses, so I was glad to find something so versatile and affordable to add to my fall and winter wardrobe.

How to Wear a Black and White Striped Dress Outfit for Fall: with black ankle boots, denim jacket, and burgundy bucket bag

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Old Navy Heavy-Knit Shift Dress // Sam Edelman Pointy Toe Flats // Lucky Brand Wedge Booties // Denim Jacket // Initial Pendant // Kate Spade Crossbody in Emerald Forest // Stella & Dot Covet Sunday Bag in Burgundy Suede // sunnies c/o Maui Jim

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26 Responses

  1. I’ve been a huge fan of ankle boots with dresses lately!! It really looks great with this t-shirt dress!
    And that dress (being stripes) is going to be so versatile, Jo-Lynne!! And what a great deal!!
    ps…I like the flats with it too—but I’m definitely partial to the booties for some reason!

  2. that is so cute on you — fun and youthful looking 🙂 a dress and boots (sandals for summer) is what i wear to work everyday so this is totally something I would wear…..I’ve been checking that dress out on Old Navy’s website and just might have to pull the trigger now……you cannot beat their prices and they have THE cutest dresses ! Have a great day.

  3. Love the dress! I also love how you styled your hair today. What size curling iron did you use to get such pretty curls?

  4. Cute outfit! I ordered those suede flats! Of course, you could also wear the dress with white (or any other color) Chucks:)

  5. I always wear dresses and skirts with ankle boots. Well, not if its boiling hot of course! Wedges are great to walk on aren t they. So easy to walk on and still have heels. I love them!

  6. I absolutely love both of these looks on you! I actually ordered this a couple months back. It was backordered and I anxiously waited over 3 weeks on it. I loved the versatility and weight of it, but it just didn’t work on my figure :/ . If it had just had a tiny bit more waist definition… I almost talked myself into keeping it anyway since I got it for $19, but I didn’t love it so I hesitantly returned it. I DO love it on you though!! The possibilities are really endless on this thing and these two looks are fabulous!

  7. you look adorable! love your style…so pretty and comfy! I’m glad I came across your blog, I’m a new admirer. 🙂
    happy day to you!

  8. Hurray! I have this dress and it hasn’t been cool enough to wear it yet; tags still on! But, now, I’m so excited to actually see it styled and in different ways! Zippety doo dah! Now, I can’t wait to wear it.
    Oh! And p.s. I realize this is not normally your style; but, I actually love the shift dress on you! But, remember the Gap dress you styled a while back? I actually loved that on you too! It’s a fun casual look! Have a great day 🙂

  9. I love striped dresses! They are really versatile and span well across the seasons depending on the accessories and footwear you style with them. I like how you styled this dress with your black ankle boots. 🙂 Melissa

  10. Oh my gosh…Don’t you just love that dress?!?!?! I bought the same one and am planning a post with it a couple of different ways as well. (burst my bubble a little when I saw you’d already done it…but I’m going to carry on ????) It
    looks adorable on you!!!

  11. This dress looks so good you! I love the look of stripes and have several striped shirts but for some reason this dress looked terrible on me. The neckline was a little too high and stiff, and the length of the sleeves hit at a really weird part of my arm (right below the elbow but not really 3/4 length and the arm opening was kinda big to roll up). I looked like I was being sent off to prison! HA! Not a good dress for a tall girl I guess.

    But….. You look great in stripes and this dress is super cute on you; I really like it with the pink flats. I bought those same flats at the Nordstrom sale in August and returned them because of the really tight fit (I even tried going up a 1/2 size) but they showed “toe cleavage” which looked funny to me. Do you have really narrow feet?

  12. I’m 5′ 6″ and I’ve found that Old Navy/Gap dresses in Tall usually come an inch or 2 above the knee–perfect for me. That dress looks adorable on you!

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