10 Outfit Templates To Master If You’re Over 40 And Sick Of Clothes

by The Candidly Team


As much as we’d like to look “put together,” the act of putting together looks we admire can get just a little… boring, tiring, tedious, overwhelming… feel free to stop us anytime and insert your own adjective. 

Even when we buy things we actually like, the problem becomes how to mix, match, and marry our clothes to create outfits we genuinely want to wear. It all feels mildly…exhausting.

 
 

What we’d really love to solve our closet fatigue (besides a live-in butler/stylist who lays out these ideal outfits each morning alongside a silver tea tray full of scones), is basically a template. 

Or maybe like 15. 

Yup, just 15 iconic, easy-to-wear and absolutely foolproof outfit templates that ensure we look equally chic to every woman who has mastered them before us. Or maybe just don’t make us look like we’re wearing yet another pair of daytime pajamas.

Quite frankly, we’ve obsessed over what looks should make up such a list, but we’re confident that our efforts can now save you some of your own precious hours of staring into the void that is your existing wardrobe.

So, without further ado, here are the 15 outfits guaranteed to look exceptional.


 
 

Image from Pinterest

 

1. This Killer Street-Style LOOK From Jennifer Aniston

 

The Skinny Jeans

Abercrombie Curve Love High Rise Skinny Jean

In a sort of surreal plot twist, Abercrombie is making some of the best jeans for curves that we’ve found. Truly. We love THIS pair because they’re super high-rise, balance hold with stretch, size up to 37, and come in five different lengths. In short, they’re better than the designer jeans that cost twice as much.

Price: $90

 

 
 

The Sleek Jacket

Open Edit Boxy Crop Blazer

We’ve searched for a version of this prototypically perfect jacket pretty much every year of our adult lives. There are a few ways to go with it, one being leather. And THIS is a gorgeous suede option at a price we’re fairly floored by. But for a non-leather option that mimics the clean lines and slim-fit of Jennifer’s, we love this one.

Price: $79.50

 

 
 

The Black Ankle Boots

Nisolo Dari Boot

This is maybe the most gorgeous bootie around, and the comfort is a million percent there. They happen to be wildly on sale at the moment, AND we loved them so much Nisolo gave us a code. Use CANDIDLY20 to get 20%. Not sponsored. Just nice.

Price: $175 - $250

 

 
 

Images from Pinterest and Pinterest

 

2. This JEAN JACKET & MIDI SKIRT PAIRING From JESSICA ALBA

 

The Classic Jean Jacket

Quince 100% Organic Cotton Denim Jacket

A jean jacket is the easiest layering piece to throw on any season and instantly look classic and cool. It’s one of very few things that have a way of making us look younger but not in a trying-to-look-younger kind of way. The way it balances with a skirt makes it a go-to uniform in spring/ summer.

Price: $50

 

 
 

The Prettiest Pleated Skirt

Aritzia Wilfred New Twirl Pleated Skirt

In addition to this being the lightest, most flattering pleated skirt that comes in no less than 7 colors we want, the waist is elastic so the comfort is endless.

Price: $150

 

 
 

The Perfect Fit Tank

Pepochic Women's Scoop Neck Ribbed Tank

A perfect fitting tank is the ideal base layer to pair with a loose midi and jean jacket. This is our favorite-fitting tank...from Amazon. Ignore Amazon’s inability to master a decent product image. This tank frames our upper body like no other, and it’s $17.

Price: $17

 

 
 

The Floaty, Waist-Nipping Midi Skirt

Free People Lowen Midi Skirt

Again, an elastic waist that makes us feel like we can actually breathe. The skirt is full enough to flatter curves but not so full it makes us look wider. It really is sort of the dream staple skirt.

Price: $60

 

 
 

Image from Pinterest

 

3. This CLASSICALLY CASJ LOOK FROM PRINCESS DIANA

 

The Effortless Button-Down

The Bennet Buttondown Shirt by Maeve

The beauty of a button-down is, of course, that with almost zero effort, we get to look completely put-together. And after years of searching, we’ve finally located the very best button-down being made. There are very specific reasons we crowned this shirt our favorite, which you can hear us go on and on about HERE, but to summarize, it tucks, ties, folds, and fits in the most flattering way. All with ease.

Price: $98

 

 
 

The Jeans That Look (And Feel) Glorious On Our Thighs and Waist

Madewell The Curvy Perfect Vintage Jean

We all need that one perfect-fitting pair of jeans that defies trends and will never go out of style. The stretch on this pair is pretty remarkable.They glide over thick thighs and big butts without gapping at the waist or sagging at the seat. We’ve never felt so well shaped but also like we can still breathe.

Price: $128

 

 
 

The Essential Loafer

Beek Moorhen Leather Loafer

Once again, this choice is all about balancing comfort with chicness. These are the loafers we slip on day after day, because they are quite simply the most beautiful and comfortable loafers we’ve ever owned. The shape and soft, buttery leather are even prettier in person. They have an almost hidden, molded arch support that feels like heaven and makes you never want to take them off. They’re one shoe we’ve been willing to invest in because we know they’ll be our lifetime loafer.

Price: $280

 

 
 

The Everyday Belt

J. Crew Classic Belt In Italian Leather

We sometimes forget how a belt instantly makes anything we throw on into a look. This one is flawless, and every time we fasten it on, oops, we’re “styled!”

Price: $29.50 - $49.50

 

 
 
 

Image from Pinterest

 

4.This Casually Chic Look from Kate Middleton

 

The Tee Every French Woman Loves

J. Crew Classic Mariner Cloth Boatneck T-shirt

We’re not sure what it is about a striped tee, but it’s one of those pieces that’s both effortless and Audrey Hepburn all at once. It’s one of 8 style pieces every French woman has in her closet. And this perfect version from J. Crew is 100% cotton and sizes up to 3X.

Price: $29.50 - $49.50

 

 
 

The Impeccably Tailored Ponte Pant

Boden Highgate Ponte Trousers

Speaking of Audrey Hepburn, we happened to finally find the perfect, stretchy, flattering ponte pant we search for every time we watch one of her movies.

Price: $98


 

The Fitted Blazer

Boden Semi Fitted Jersey Blazer

A gloriously stretchy, jersey blazer from a classic British brand. It fits superbly well and mimics the natural curve of our waistline.

Price: $180

 

 
 

The Comfy Espadrille Wedge

Eric Michael Teva

Call them the little black dress of sandals, these espadrilles win lots of points for being wildly comfy with plenty of arch support, and of course, looking easily elegant with pretty much everything we wear.

Price: $145

 

 
 

Image from Pinterest

 

5. ThIS Pretty, Black Maxi Dress LOOk From Jennifer Aniston

 

The Endlessly Flattering Maxi Dress

Marcella Clara Dress

This dress is not only blissfuly comfortable but wildly flattering. In fact, the thrill we felt when we discovered it/ tried it on ourselves is fully documented HERE. It may be the easiest piece to pull from our closet any weekend day or summery, going-out-to-dinner evening to look instantly chic and lovely. We wear it with our nicest sandals and softest cardi, so we feel like we’re home lounging whilst looking entirely put-together.

Price: $118

 

 
 

The Chic, Non-Black Handbag

Marcella Kelly Tote

Sometimes the best way to elevate your entire look is to simply select an accessory in a non-neutral color. This handbag in “bone” makes anything we where instantly more alluring and chic. In fact, you can one of us model this exact bag with the above dress. The combo is effortlessly chic, and no one has to know how cozy we feel wearing it.

Price: $198

 

 
 

Image from FootwearNews

 

6. ThIS Flawless White TEE Look From Jennifer Lopez

 

The Best White Tee You’ll Ever Own

Everlane The Air Scoop-Neck Tee

It’s a lot harder than it sounds to track down a simple, flattering white tee that fits the exact way we want it to, but alas we found THE ONE.

Price: $30

 

 
 

a Long Wide-Leg Jean

Madewell Kick Out Full-Length Jeans

A gloriously long, sliiightly kick flare jean can be as chic and flattering as your most tailored pants. This pair sort of dresses up our simplest looks, making our laziest jeans and tee combos into actual outfits.

Price: $138

 

 
 

The Comfiest Of Wedge Sandals

Franco Sarto Clemens Espadrille Wedge Sandal

We love a wedge for comfort and support, but this one also happens to elevate our whole outfit, so our casual jeans-and-tee combo suddenly become an actual “look.”

Price: $48

 

 
 

Image from Pinterest

 

7. This CHIC BLACK AND WHITE Look From NAOMI WATTS

 

The Winning White Blazer

Favorite Daughter The Suits You Linen Blazer

This blazer is one of our favorites, because it’s perfectly oversized but has the cleanest, crispest lines. Plus, it dresses up for more formal occasions.

Price: $378

 

 
 

The Wide-Leg Jeans Of Our Dreams

Paige Anessa Crop Wide-Leg Jeans

The struggle to find a pair of soft, stretchy wide-leg jeans that don’t gap at the waist or sag at the seat has felt somewhat endless. That is until we discovered these jeans. They’re perfect on curves; you can see them on a non-6ft-tall model HERE. They’re more than we’d normally spend on a single pair of jeans, but we’re wearing them 3X as often as any other pair in our closet.

Price: $229

 

 
 

The Softest Black Tee

Z Supply Modern Slub Tee

A good ol’-fashioned perfect quality tee. Whisper soft and the fit is excellent.

Price: $39

 

 

The Graceful White Sneak

Dr. Scholl’s Women’s Time Off Sneaker

Despite being Dr. Scholl’s and therefore orthopedically comfy, these sneaks are truly chic. Like a ballet flat. And they match everything we wear.

Price: $70

 
 

 
 

Image from Pinterest

 

8. This PERFECT FALL LOOK FROM CAREY MULLIGAN

 

The Sleek Coat

Yousify Womens Notched Lapel Collar Double Breasted Pea Coat

We all want the sleek lines and pretty proportions of a perfect, chic fall coat. But get it in an interesting color and suddenly you’re not dressed like everyone else. Of course, this one also comes in every neutral shade we typically lust after - at a price where we can afford to get it in more than one color no less.

Price: $60

 

 
 

The Striped Sweater

J.Crew Heritage Cotton Rollneck™ Sweater

Wearing a stripe on your gorj pullover is yet another way to elevate your look and make it look more “styled.”

Price: $52.50 - $89.50

 

 
 

The Impeccable Trousers

The Avery Elastic-Back Trousers By Maeve

These happen to be the pants we talk about any time we mention the most flawless , tailored, flattering trousers in the world. We go on and on about them HERE. We even show you what they look like on a real person who isn’t a 6ft tall model. But the point is, if you’re going to buy anything on this list, do yourself a favor and but these pants.

Price: $148

 

 
 

Image from EOnline

 

9. This Elegant, Yet Easy-To-Wear Look From Jennifer Aniston

 

The Exceptional-Fit Tee That Can Dress Up

Skims Cotton Fits Everybody T-Shirt

This tee from Skims is entirely about the fit. It just looks great on everyone.

Price: $48

 

 
 

The Cropped Wide-Leg Pant

Maeve The Colette Cropped Wide-Leg Pants

Anything wide leg with stretch that still shows off shape is a winner in our book. THIS cropped pair stands alone when it comes to fitting smoothly and looking sophisticated.Whatever it is, the way you tell your story online can make all the difference.

Price: $120

 

 
 

Image from Something’s Gotta Give | Columbia Pictures

 

10. This “Coastal GrandmoTher”Look From Diane Keaton

 

The Easy, Drapey Pant 

J. Crew Sydney Wide-Leg Pant In Bi-Stretch Cotton Blend

One of our favorite pairs of easy, wide-leg pants with just a wee bit of stretch, so we get to feel like we’re still in pajamas.

However, if you’re searching for a pair in black, THESE pants from Aritzia are the stuff of dreams, nipping at the waist and nailing the shape, drape, and subtle movement we strive for in a tailored trouser.

Price: $44.50 - $56.50

 

 
 

The Only Turtleneck We Actively Love

Everlane The Pima Micro-Rib Turtleneck

Of all the components that go into the “Coastal Grandmother” look (and we sourced all of them HERE), the turtleneck might just be the most iconic. And yet, if you’re anything like us, you still need to be sold on this particular style. THIS is the turtleneck that finally convinced us, with its light and dreamy-feeling ribbed texture and the beautiful fit that gives us glorious lines no matter what we wear it with.

But if a turtleneck will just never be your thing, the crewneck version of this shirt happens to be our favorite long-sleeve tee in on this planet.

Price: $50

 

 
 
 
 

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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