4 Outfit Templates To Dress Like A “Cool Mom”
We swear, the clothes are cooler than the title.
Image from Gilmore Girls | WB
by The Candidly Team
There’s something intrinsically uncool about calling yourself a “cool mom.” That’s sort of the fun of it though. Like we’ve been liberated from any existing pressure to be cool, and now we make the rules.
Which, come to think of it, maybe we do.
Sweat sets are chic now. Chunky shoes are sexy. Wildly oversized sweaters are all over TikTok.
Coastal grandmother be damned - are we in the era of the “cool mom?”
Image from Mean Girls | Paramount Pictures
And obviously, none of this is really about being cool at all. It’s about not assuming that because you’re a mom and because you have 437 things to think about besides getting dressed in the morning that you don’t care if you look like a heaping pile of textile waste when you walk out the door.
It’s about still feeling like ourselves and still connecting with a way we like to look and dress and not suddenly styling ourselves like we’re 1000 years old just because we want to be uncompromisingly comfortable.
Well, there is a way to have it all, where clothes are concerned, a way to look cool and chic and completely cozy all at once, and it’s by choosing pieces that:
1. You know look good on you even on days you're bloated and your hair is greasy and you're totally uninspired.
2. Are tailored and chic, but basically feel like athleisure
3. Make you look styled all by themselves. One. And. Done.
There are a few basic principles that make this possible:
Cozy materials
Fits that create your most flattering shape
Smart layering
But to really illustrate what we mean by all of this, we created 4 templates that we, (as moms/ non-models/ women who have sailed north of 35), turn to constantly to look like the “coolest” version of ourselves. They’re foolproof in terms of making us feel our best even when we have zero energy to put toward looking our best.
And here they are:
LOOK #1
The Lazy Dress
Are we coming in hot by starting with a dress? We like to think so.
Dresses are famously hard, but when you find one that works beautifully on you, they’re nothing short of a savior, stylistically speaking. We all want something we can throw on and go - an alternative to shorts on warm days, a way to look more zhuzhed and chic when we’re tired of just jeans all the time.
And we’ve figured out that our dream of wearing a dress as comfortably as we do jeans boils down to dumb words like “balance” and “proportion,” which sound vague and meaningless but matter a lot in the physical world of getting dressed. Basically all they really mean is this: wear a bunch of baggy, chunky shit, and you’ll look frumpy and blah. Wear only fitted, slight pieces, and you’ll look like something’s missing, not to mention you’ll be self-consciously readjusting all day.
So, here is the formula for creating the perfect dress look:
The Dress: Think of your dress as a base layer. A column style like THIS is great if you like to show a little shape and a fit-and-flare like THIS, which happens to be the most universally flattering dress in the world, is ideal if you like some tum coverage. THIS particular column dress shown above is a dream, because it’s made from the same smoothing material as yoga pants, so it completely holds us in while feeling like buttery leggings.
The Jean Jacket: An excellent-fitting jean jacket is a gal’s best friend. Throw it on over anything, and poof, you’re cool. It’s light enough to toss on over something sleeveless and roomy enough to layer over sweaters. And when it’s just a bit boxy and sliiiiightly cropped like THIS one (our favorite!), it makes our entire body underneath look narrower. And we feel comfortably covered, even in our tightest things.
The Slides: We all just want to be wearing a shoe we can slide on and off at any moment, correct? But it’s always a bummer to feel like we lowered our overall chicness level by choosing a boring, albeit comfy shoe that’s basically just a slipper. THIS pair from M. Gemi feels so much more gorgeous and luxe than any other slide, but it’s still casj enough to wear daily. The bit of blockiness adds that balance we were talking about, so you don’t look top-heavy, like an upside-down triangle in a dress.
The Bag: Hang out with us long enough, and you will hear us bring up THIS bag - probably more than you’d care to. The reason is it is decidedly the best bag we’ve ever owned. It’s crossbody which makes it a part of your outfit, creating yet another line across your lovely curves and a little more coverage for those who care for that sort of thing.
The Scrunchie: There’s some magic in throwing your unruly hair into a ponytail with a GIANT scrunchie. First off, it adds lots of bulk, so even if you have like 17 hairs, they’ll look fuller. Second, a pony itself is like instant-youth. So win-win.
Of course, there are many ways to layer this dress look with any spacious piece of outerwear or a more dressed-up shoe. For example…
The Cardigan: THIS beautiful cashmere cardigan is divinely oversized and costs 1/3 of the price of that other famous cardi that you can barely tell it apart from.
The Flats: If you’d call yourself a flats person, THESE are without a doubt the most comfortable, breathable ballet flats you’ll ever slip on. They come in like 36 patterns and colors, though we do like a leopard print as a classic and immediate trick to make us look fully “styled.”
The Cashmere Cap: We’re not washing our hair all the time. We’re not even supposed to. THIS is our laziest/ chicest way of hiding it.
The Glow: No matter what we wear, our face is there to give away that we got 4 crumby hours of sleep and forgot to drink water til’ noon. We have a secret trick to counter this, and it’s THIS SPF, which is radiance in a bottle. It’s all our very own Editor-in-Chief is wearing in the above photos. Not a smidge of makeup.
SHOP THE LOOK
LOOK #2
The not-boring “jeans and a sweater”
If you’re saying to yourself this is just a sweater and jeans, you are quite correct. Realistically, most days, we just want to be wearing our coziest sweater and most flattering jeans. But there’s a wee bit of a hack to this look that elevates it slightly and makes it more flattering, all while feeling remarkably good on our bodies.
The Sweater: The shorter length of the sweater with the high-waist jeans makes you look elongated. Already, $60 for a sweater that’s as feathery soft as its cashmere counterparts is a yes for us. But the fit is what sets THIS one apart. It hits below the top of your pants, so no belly to be seen, but the shape is very skimming, and there’s tons of space in the arms, which means zero restriction. Because of all this thoughtful tailoring, the shape itself doesn’t age us the way some sad, sacklike cardigans can.
The Knit Coat: The LENGTH of THIS coat makes you look “smart” as the Brits say, but it’s also a total hack cuz it’s made of sweatshirt material so you essentially feel like you’re walking around in your coziest blanket. It’s soft as all heavens and has a weighted feel while being very sleek and slim, so it makes everything we wear under it look more polished. And we can wear it year-round. The plaid is great for making everything come to life, but it comes in the most perfect neutral solids as well.
The Jeans: THESE are our absolute go-to everyday jeans. We own them in every wash they come in. No pair is as comfortable round the waist. And the sailor shape is supremely flattering on hips and thighs. They also come in two lengths, so you can choose your own personal crop level.
The Boots: Find one pair of timeless booties with arch support and a block heel, and they will trick anyone who sees you into thinking your whole outfit is super chic. The key is that you need them to feel like you’re in tennis shoes or flats, and you do with THIS pair.
The Necklace: We like our more pronounced jewelry to 1. Mean something and 2. Be artful and alluring. THESE coin necklaces from Jane Win spoke to us, which sounds very corny, but it’s true. Each one has a special meaning. Plus, we can wear it all on its own and look completely accessorized.
The Sneakers: This whole outfit also goes with white sneaks, so no prob if you can’t bear your feet being at even a billionth of an inch incline.
SHOP THE LOOK
LOOK #3
The Elevated Pig
Leggings can 1000% be worn as a real “outfit” like this and not look like you’ve given up. It’s all about mixing casj with chic and high with low.
The Coat: THIS is unequivocally THE best coat, not in small part because the arms are huge, so you can literally wear 3 sweatshirts under it and you won’t feel like the Michelin man.
The Leggings: We talk often about THESE being the most buttery soft and smoothing leggings in the world. Our desire to live in them 24/7 was maybe our biggest motivator for finding a way to style them into something we could wear daily and feel as put together as we would in a perfectly tailored trouser.
The Sweatshirt: This is what we meant when we said “high/low.” THIS cozy, striped Amazon sweatshirt is a lovely dupe for many we’ve seen being sold by high-end French labels, and it’s just as chic. But $24.
The Bag: Adding a pop of color when the rest of your outfit is neutral is a glorious trick for looking like you’re stylish even if you’re not a style “person.” THIS petite crossbody also happens to be a more compact version of the miracle bag we talked about earlier.
The Cozy Boots: Yes, THESE are UGGs, and yes, they’re a bit of a trend at this moment, but coziness paired with actual height and support makes it a trend we fully support.
The Cap: Few things solve our inner crisis of being exhaused/ wanting to look chic as well as THIS cashmere cap.
The Pigtails: They really put the “pig” in elevated pig but are absolutely ideal for 3-min-in-the-morn days when you still want to look cute.
The Skin: Is skin part of an outfit? It definitely is. Especially if you’re an elevated pig. Our EIC, Audie, is wearing only 2 things—because when you have 14 seconds to get ready, the focus should be on skin. THIS dewy SPF that triples as a moisturizer, spf, and tint. And THIS blush which gives the most blindly but natural glow in the history of time.
And if you’re wanting a more spring/ summer version of this fall/winter ensemble, here are the perfect swaps:
The Jean Jacket: The SAME jean jacket mentioned above, but we didn’t mention that it has big enough arm holes, so you’re not squeezed, and the size range is amazing.
The White Sneaks: A HUGE platform helps to balance looser upper layers (as well as a bigger butt).
The Hat: Here’s that pop of color again, but this time it’s in the hat. The green weirdly goes with everything. The exact one pictured is hard to track down, but THIS one is also a favorite and very similar.
The Bag: Ok, yes THIS bag is a little high in the high/low category, but it’s a great quick-errand bag if you don’t want to lug around your enormous suitcase bag full of crap, and it just houses your wallet, phone, and keys to have on you at all times like a baby Sherpa. We believe in splurges on bags cuz they’re so wearable with a million outfits unlike splurging on a skirt let’s say which is likely going to be worn three times per year. The cost per wear ends up being incredibly low, which isn’t just a rationalization but an actual solid reason for investing in anything.
SHOP THE LOOK
LOOK #4
The mindless set
Everything on this list up to now has something in common in that it all looks like nice, tailored clothes you can happily wear out, but every single piece feels like you’re in loungewear. So it’s fitting that we’d end with the thing many of us wear most, which is actual loungewear. Well, sort of. It’s a set. A set can technically be loungewear but it’s miraculously considered chic. Especially THIS set. We wear it everywhere, and it might be our favorite thing. Here’s why.
The Set: We kept THIS knit set in our cart for months, because it was wildly pretty and looked soooo good on, but we thought, surely it couldn’t be as comfortable as our silky sweats. When we finally took the plunge, our delight was two-fold. First, it hangs gorgeously - better than we even imagined. But second, the quality was waaaay beyond what we expected. It’s leisurewear at its finest. Soft as all heavens, thick, weighted but cut to be flattering instead of bulky. We fear we must order it in more colors. But be warned: 8 bjillion people will ask where you got it when you’re out and about, which you will be because it’s NOT just sweats.
The Sneakers: We love the fact that sneakers are as elegant as ballet flats these days. But THESE are honestly the gold standard in sneaks that we can dress up or down.
The Bag: It’s been established that we’re not gonna shut up about THIS bag. Here it is in a woven leather, which is a clever way to make our casual outfits look just a wee bit more luxury … but not in a loud way. Like we said, it’s all about that balance.
SHOP THE LOOK
At The Candidly, we try a lot of stuff so you don’t have to. We only recommend things we truly love, and that we think you’ll love, too. All products are chosen independently by our creative team, and all details reflect the price and availability of products at the time of publication. If you buy something we link to, The Candidly may earn a commission.
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