The next best thing to yoga leggings? This dress. I kid you not.

It feels like workout wear –but it’s a dress — one that is actually pretty and verifiably comfortable. What I love and appreciate about this dress in particular, is that I can simply put it on and instantly feel like a real human being (ohmygosh!). One who still knows how to get dressed (wow!)…but also someone who can still get on with her day as a mom/faux homeschooler/event planner/PE teacher/I don’t even know anymore…all the things?

How To Style A Black & White Striped Dress: 10 Outfit Ideas

Also, I can’t say no to a striped article of clothing. Maybe it’s the Northern, East Coast girl in me, the one who went to an all-girls’ private school, that makes me gravitate to the ultra preppy lines. Or maybe it’s the fact that I am just super-chic like Coco Chanel (I’m leaning more towards the latter, honestly). Either way! I love a good, classic stripe.

So, I took off my yoga attire, put on the pretty striped dress and pieced together a few everyday outfits…10 to be exact.

Outfit Idea 1. Striped Dress + Doc Martens

This one doesn’t really need any explanation. You wear the dress with the Docs and yaaa good. I love it, actually, with its simply cool vibe. If I were leaving the house (which I won’t be much [sob], I’d grab a Julian backpack to go along with this).

Comfy like leggings = this black & white striped dress. Pretty + Fun. Wear it w/ Doc Martens, Birkenstocks, Golden Goose, sandals & booties. 10 outfit ideas.

dress (+ similar at Nordstrom) | doc martens (I’m wearing a size .5 down)

Outfit Idea 2. Striped Dress + Draped Cardigan + Gladiator Sandals

This is totally and completely my type of thing — a comfy dress, long, slouchy layer, and a cool, studded sandal. I had these exact sandals, but in brown for years…and then they died (a sad day). I then found them in white a few months ago and couldn’t order them fast enough. I love how the bright white highlights the crisp white of the dress. Matchy matchy in a good way.

Comfy like leggings = this black & white striped dress. Pretty + Fun. Wear it w/ Doc Martens, Birkenstocks, Golden Goose, sandals & booties. 10 outfit ideas.

dress (+ similar at Nordstrom)| cardigan jacket (similar + kimono option here) | sandals

Outfit Idea 3. Striped Dress + Golden Goose Sneakers + Track Jacket

I mean, had to. I have to always ask myself the question — no matter the article of clothing — “but will it go with my Golden Goose?”. If it does, I am more apt to purchase “it”. Life is so much easier, having a pair of sneakers that can go with virtually anything.

Comfy like leggings = this black & white striped dress. Pretty + Fun. Wear it w/ Doc Martens, Birkenstocks, Golden Goose, sandals & booties. 10 outfit ideas.

dress (+ similar at Nordstrom) | golden goose

…Now With That Track Jacket

Now, yeh. It can’t hurt to spice it up a bit and add an ever-loving track jacket to the mix. The stripes and red down the sleeves give the entire everyday outfit look a good kick in the patootie…and I love a good kick in the patootie (when it’s fashion-driven).

Comfy like leggings = this black & white striped dress. Pretty + Fun. Wear it w/ Doc Martens, Birkenstocks, Golden Goose, sandals & booties. 10 outfit ideas.

dress (+ similar at Nordstrom) | jacket | sneakers

Outfit Idea 4. Striped Dress + Sweatshirt + Bright Footwear

I wish I had a cropped version of this sweatshirt, honestly…and I *almost* took the scissors to this one, but stopped myself. I can’t chop all of my sweatshirts, because then where will I be when I actually need a cozy sweatshirt, one that doesn’t show a snippet of midriff? (and I’ve gleefully cropped them all like a 16-year-old TikTok star) That would be a fun little moment, where I stand there contemplating my life and wondering if I even know how old I am.

So, I’d say…yes. This ensemble below would look better, in my opinion, with a cropped layer over top. It would then show the lines of my waist a bit and add some length to the look, which…we all know how badly I need length. (I can feel S’ eyes rolling now as I am typing this) Now, the best part of this outfit is the red Everlane Day Heels. I LOVE THEM. I do advise going up a half size, though, because even though they do fit me, I think I would be slightly more comfortable in a 10.

Comfy like leggings = this black & white striped dress. Pretty + Fun. Wear it w/ Doc Martens, Birkenstocks, Golden Goose, sandals & booties. 10 outfit ideas.

dress (+ similar at Nordstrom) | sweatshirt (similar here + here) | heels

Outfit Idea 5. Striped Dress + Denim Jacket + Western Boot

Prepster gone Country gone…Anine Bing? I don’t know. I’m going with it. The whole easy and casual style and feeling of it all really gets an upgrade with a pointy-toed western bootie. Also, a ball cap is really a great way to be OKAY with not having seen your hairdresser in months.

Comfy like leggings = this black & white striped dress. Pretty + Fun. Wear it w/ Doc Martens, Birkenstocks, Golden Goose, sandals & booties. 10 outfit ideas.

dress (+ similar at Nordstrom) | jacket (similar) | boots | hat

Outfit Idea 6. Striped Dress + Floral Button-up + Lace-up Sandals

Ooooh, this is so pretty. I want to wear it out to a brunch with my girlfriends, which…I actually don’t ever really do (who do I think I am? Carrie from Sex & The City?), BUT I think I it’s about time that I start a monthly brunch club once all of this pandemic stuff is over. I’d wear this and walk in like the world is my runway, because I’VE BEEN STUCK INSIDE WITH THREE KIDS FOR TOO LONG AND DAMN IT I WANT TO STRUT. IT. UP.

Comfy like leggings = this black & white striped dress. Pretty + Fun. Wear it w/ Doc Martens, Birkenstocks, Golden Goose, sandals & booties. 10 outfit ideas.

dress (+ similar at Nordstrom) | button-up | sandals (similar) | sunglasses

Outfit Idea 7. Striped Dress + White Blazer + Superstars

This one surprised me because I thought it would be too much white (and maybe it is to you all looking at it) but…I dig it! I also like how the Adidas stripes play-up the thinner stripes in the dress. TIP: don’t wear around grumpy 3-year-old wielding Danimals like a weapon, because he “doesn’t wannnaaaaa put his pants on” (full-on meltdown ensues, yogurt ev-er-y-where).

Comfy like leggings = this black & white striped dress. Pretty + Fun. Wear it w/ Doc Martens, Birkenstocks, Golden Goose, sandals & booties. 10 outfit ideas.

dress (+ similar at Nordstrom) | blazer | sneakers

Outfit Idea 8. Striped Dress + Cashmere Pullover + Birkenstocks

Oh, wow. OKAY. I could have noticed how very pilled this sweater is and taken the time to shave it, goodness. I guess I was in a different place in my brain — the place that says, “everything is fine, this is fine, we’re all going to be fine”. Sorry, ya’ll. This is not a great representation of what this outfit could be at it’s full potential!

I think you might be able to squint your eyes and see what it could look like — soft, cozy pullover cashmere with a comfy striped dress underneath. Don’t forget the Birks, because they are the cherry on top (or bottom, I guess). I’d wear this all around the house, while homeschooling (Lord, have mercy), cleaning up (haha I don’t do that anymore), sipping coffee (lots of coffee) or, attempting to escape into a book while my family runs rampant around me.

Yeh, it’s a good outfit.

Comfy like leggings = this black & white striped dress. Pretty + Fun. Wear it w/ Doc Martens, Birkenstocks, Golden Goose, sandals & booties. 10 outfit ideas.

Uhhh. That Sweater Needs To Be Shaved.

That’s better. lol. If all else fails and you do not have the brain power to clean up your cashmere, just tie it around your waist and pretend that it has a purpose.

Comfy like leggings = this black & white striped dress. Pretty + Fun. Wear it w/ Doc Martens, Birkenstocks, Golden Goose, sandals & booties. 10 outfit ideas.

dress (+ similar at Nordstrom) | sweater (similar) | birkenstocks

Outfit Idea 9. Striped Dress + Belt + White Bootie

This might be my favorite. The belt cinches in the waist a bit and brings some interest. Also! These adorable booties have the perfect cut to elongate my legs, which again…is something I so desperately need (stop rolling those eyes, S!).

Comfy like leggings = this black & white striped dress. Pretty + Fun. Wear it w/ Doc Martens, Birkenstocks, Golden Goose, sandals & booties. 10 outfit ideas.

dress (+ similar at Nordstrom) | belt (similar skinny here + really similar chunky here) | booties (went down .5 size)

Outfit Idea 10. Striped Dress + Sleeveless Cotton Dress + Cap-Toe

Stick with me for a second! I know this is a bit…much, considering the fact that layering a dress over a dress is maybe not very realistic. HOWEVER, why the F not at this point? I really love the long-sleeve stripe against the bright pop of color. It’s FUN…and we all need some fun sometimes. So, who cares if you’re wearing two dresses at once?! The time to live is now! The time to explore and do things you haven’t done before is now!

K. I’m tired now from that soapbox pep talk. I think I’ll go take a nap in my two dresses (and by nap I mean, close my eyes while the kids ask me 10 million questions until I give up and open my eyes).

Comfy like leggings = this black & white striped dress. Pretty + Fun. Wear it w/ Doc Martens, Birkenstocks, Golden Goose, sandals & booties. 10 outfit ideas.

dress (+ similar at Nordstrom) | cotton dress (similarlove) | cap-toe slingback

Shop Comfy, Everyday Striped Dresses

The dress I styled above is from Sonnet James and you can find it here. Everything is 30% off right now, by the way — use code SPRING30 at checkout. Below are some other striped dresses that can be worn every day — ones I think you will appreciate and style-up in a multitude of fun ways…And as always, if you do — share it with us! (IG: @themomedit).

Cheers,

Cams

Find me over on the gram (@camilledipaola) for more #TotallyCasualMotherhood moments.

6 COMMENTS

    • Ya know, I didn’t even know they had tall sizes – awesome. Thank you! I am actually wearing the normal Small (I’m 5’10). I think it depends on how long you want it, so if you like more of a midi dress…go with that one. I am now intrigued about how that length would look. I think it could really, really rock on someone with a long leg. Cheers.

  1. Super cute. What is the sizing like for the adidas joggers from Amazon that were in TME stories the other day? Not worried about the length, more so the waist, if it squeezes or tends to be tight. 5’9” 160lbs
    I’m a snug but doable size 10 or M/L depending on fit.
    Also, any more TCMotherhood pods? I really enjoyed them!

Leave a Reply