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Should You Wear a Dress With Leggings?

Dress with leggings

My absolute two favorite articles of clothing. The dress. The leggings. They are both effortless and classic and can be interpreted in a million different ways.

Everyone has an origin story, but I love the twist in this one. Originally, they were worn by Scottish men according to Who What Wear. Just like the boyfriend jean we stole it and made it our own. But we can argue that the leggings of oh yester year (I know not Scottish but…) are quite different than what we consider a legging today.

Eat your heart out.

What we are really talking about is that garment that has stretch that forgives you for drowning your sorrows in a tub of rocky road ice-cream yet picks your ego back up and hugs you tightly and makes you feel secure. She doesn’t ever make you feel fat and will never body shame you, she is your most trusted friend. She’s always there for you. She is lightweight weight, and she is a force all on her own. She’s been through hell and back and she hasn’t always had the best reputation. Yes, I’m still talking about leggings.

We really got to know the legging as it is today starting in the 50’s with the invention of Spandex. A brilliant creation of stretchy goodness that has revolutionized the apparel industry. Spandex is in whatever your heart desires. You got that right.

Sakkas 1824 - Alvita Women's V Neck Beach Dress Top Caftan Cover up with Rhinestones - TRM94-Multi - OS

I said it once and I’ll say it again. I love the 60’s and when mirrored for my love of the legging it’s no big surprise that this decade was the first to adopt leggings into fashion. Remember those cute little shift dresses? They wore them over leggings. Leggings and dresses, the first love story. Once the 70’s came along, and women started burning bras they were taking off anything that was confining them. The only ones left to wear them? The bad girls. Didn’t you see Grease? Yea the part when good girl Sandy goes bad? Smoking cigarettes and red lipstick boy did that cram a stereotype down our throats. Olivia Newton John wore them well and that was the days before photoshop, I think. Bless her. I guess even looking as good as her in them doesn’t spare one of a broken heart. What was good for Jane Fonda made everyone just say enough is enough with the leggings for a while. I don’t see how it could go any other way Jane Fonda is a God and she wasn’t sweating to no oldies but she was a shiny vison of perfection.


Rebel yell.

I had a short rendezvous with them in the early nineties, but then on to something else also known as business casual, that was fun. About 15 years later I can remember sitting at a bar in Mandalay Bay with some of my colleagues having a cocktail after a long week of trade show shenanigans and up comes leggings. We all groaned and swore we would never ever wear them ever again nor any of these skinny jeans that were emerging again only this time with spandex. If there is one thing about me, ain’t nobody the boss of me, not even me (it’s true) so as soon as I got back, I bought a pair of Hudson skinny jeans at Nordstrom and it just so happened that on my next trip to Target I noticed they had a black shiny faux leather pair of leggings. Yes, I snagged them, they were 10 bucks and if nobody else was going to wear them I surely was. I’ve been wearing them ever since. While they aren’t as shiny as they originally were they are still hanging on and nobody would ever know I’ve had them over 15 years. I just wore them the other day and the finish looks better than my two-year-old Spanx. I’m not making it up.

SPANX Women's Faux Leather Leggings 2437, Black, Medium

Please wear leggings with dresses. Just don’t wear Nike or any other athletic leggings with that dress. I know we have all blurred the lines here, but I firmly believe that athletic wear should never be paired with something special. It’s one of my pet peeves to see that extra think reinformed seam that is required for sport leggings it’s not just the best for cutesy dresses and tops.

Long dress and leggings

Do’s and Do absolutely not

Generally, really form fitting stretchy dresses is a big old no no to wear with leggings but a silk shift, sure.

Definitely wear leggings with short dresses.

Don’t wear leggings that are too thick, just a single small knit is perfecto.

Don’t wear them with long dresses unless I guess it’s cold.

Oh, wait wear them with long dresses if the said long dress is sheer or lacey.

I wouldn’t wear leggings with a dress the goes past mid-thigh unless of course if wearing as above.

Don’t wear formal dresses and leggings.

I don’t want to see leggings that have zippers on the bottoms with dresses either. They should be just a nice compliment and finish your outfit.

I say the thicker the leggings the higher the hem. Sorta like the bigger the hoops the bigger the never mind. It’s just a saying and I’m not afraid to admit I like big hoops and I cannot lie.

Put on some leggings and try all your dresses on. You’ll see what I’m saying about having the right hem for the right thickness of legging. You can’t go wrong with anything short and flowy with some leggins. Urg that word leggins and why can I picture Paul Rudd standing in from of the mirror just repeating that word? Leggins. Leggins. Leggins. I digress, sorry.

Roll it, roll it, roll it.

Get the lint roller and spruce those babies up. I know the little pills can be so annoying. I’m over sweater shavers I use a regular disposable razor to refresh my leggings or whatever and then just de-lint it. It works wonders. I’ve been sitting on a bottle of black Rit Dye in hopes that one day I’ll revive some of my washed-out favorites but not today and not this article.

Ha ha man I need help because this has me thinking about dresses and jeans. I know that’s not for everyone but once in a while, when all the stars have aligned there is a little bit of icon status that can happen. We aren’t going down that rabbit hole today, you’re welcome.

Just like I always say I don’t like everyone (I mean if your energy is bad, thanks but no) so everyone doesn’t have to like me (rude) LOL. Not all dresses like leggings and not all leggins like dresses. It’s kinda like the mullet of fashion fancy on top but ready for activities on the bottom. Noooooo, I still don’t think you should be wearing your workout leggings with dresses, remember! Just saying.

It’s winter and nothing is better than making sure you’re covered, and the D&L is a winner. The best part? When you come home you get to one pull off of the dress and one pull on of the sweatshirt. Easy breezy.