Is This The Secret To Making Really Casual Outfits…Cool?


Anyone else been watching “wearing vs. styling” videos on TikTok or IG? These are videos that compare a base outfit (top, pants, shoes) to that same outfit styled up with accessories and cool outfit hacks like cuffing pants, rolling sleeves, etc. This article is kinda like that, but think of it as Wearing Vs. Styling Step 1.

Before we go any further, I feel like I need to properly set expectations: ‘good enough’ outfits are, for this article, good enough. I’m not going to talk about anything groundbreaking, and – admittedly – even my use of the word, “cool” will be debatable. But for those deeply casual outfits: think leggings, think joggers, think…just rolled out of bed in husband’s tee and need to walk the dog/get kids to school/whatever…I have a small trick I’ve been using for years. This trick is part of the whole “wearing vs. styling” thing, but done in a prescriptive kind of way (something I find easier to execute once I’m busy, rather than starting from scratch).

Case in point: Earlier this week, I had one of those really busy mornings where I couldn’t quite get on top of anything and suddenly I was about to let a whining, barking dog out of her crate and knew she needed a walk, like, NOW. And while I don’t *always* care about my outfit for early morning dog walks, this one…wasn’t great. And don’t worry – I have a visual:

how to make outfits better

similar tee | shorts (s)

And since our dog is still a puppy (albeit a giant one), I need sneakers to walk her. Which, normally, would be fine, but these were the sneakers I had closest to the door:

styling vs wearing

similar tee | shorts (s) | Sneakers

I normally love these sneakers, but they aren’t going to save this outfit on their own. So now, I had a choice: change my outfit or – aha! – try my casual outfit styling trick, the Step 1 of “wearing vs styling”.

The Trick To Making Casual Outfits Better: Find A Bag, Shoe & One Cool Accessory…That Matches

I’m not normally one for matching shoes/bag/whatever, but I’ve found that with deeply casual outfits, accessories that go together, accessories that look like they were intentionally chosen, go a long way to ‘saving’ an outfit. Even one as bananas as the one I was wearing that morning.

how to make casual outfits cool

The Accessory Set: Sunglasses | Belt Bag | Sneakers

The clothes: similar tee | shorts (s)

So the first step in the whole “wearing vs styling thing” is to figure out a shoe and bag pairing that matches. Then, to really take the look up a notch – and listen up, this is the important part – find ONE additional accessory that goes with the shoes & bag you’ve chosen. Sometimes it’s sunglasses, sometimes it’s a baseball hat, sometimes it’s a winter beanie – it could even be cool earrings. The key is that all three pieces are intentionally chosen, go together, and fit the vibe you’re going for. In my case, the vibe was casual.

I call this trio of three matching pieces an Accessory Set. Here’s an example of a few accessory sets that work particularly well with casual outfits:

how to do wearing vs styling

This is the easiest way to get out the door looking – relatively – cool. While matching shoes & bag always helps, it’s the addition of one other accessory that really makes the look pop. This technique works so well that I sometimes even print out photos of these Accessory Sets, just to reference while getting ready.

In fact, even fancy outfits benefit from a well-chosen Accessory Set. Finding a killer evening clutch + shoe + earring pairing is often all I’ll need to make a denim outfit night-out ready. 

But for now, I’m talking about casual outfits. And once you have a casual Accessory Set pulled together, it literally works with alllll the easy outfits.

Example 1: A Cool, Casual Outfit With Leggings

cool outfit with black leggings

GAP hoodie (s) – on sale!! | leggings (s) | Sunglasses | Belt Bag | Sneakers

Here I’m taking that same accessory set and adding it to one of my most-worn outfits for school drop-off. A deeply casual outfit like this one benefits from matching accessories simply because it’s the most obvious way to make the outfit look intentional.

Example 2: A Sweatpants Outfit I’d Wear Out Of The House

wearing vs styling joggers

similar tank (m) | joggers (m) | Sunglasses | Belt Bag | Sneakers

Let’s go even more casual, shall we? While one could argue monochromatic outfits will always look a bit chic, this outfit is as easy as it gets. It’s the three accessories that pull this look together.

Example 3: Running Shoes & Jeans? Still Yes.

how to wear sneakers with jeans

Madewell cashmere sweater (s) | similar jeans | Sunglasses | Belt Bag | Sneakers

The good news, too, is that if you figure out a casual accessory set that involves sneakers…it’s a really good way to wear your sneakers with everything. Our article, How To Wear Colorful Hokas With Jeans, illustrates the power of small but matching (or at least coordinated) Accessory Sets.

Last Tip: Incorporate A Jacket

Now that the weather is getting cooler, incorporating a jacket into these Accessory Sets is both useful and adds another style element. While trench coats and beautiful wool wrap coats might be my first choice from a style perspective (they can take any outfit next level, including and especially sweatpants, leggings, etc)…I don’t always want to wear such nice pieces walking the dog.

wearing vs styling black leggings

similar fleece jacket | GAP hoodie (s) – on sale!! | leggings (s) | Sunglasses | Belt Bag | Sneakers

Bottom line? Don’t overlook how well casual pieces like fleece jackets, puffers, or windbreakers can add style to your most casual outfits, as long as they’re added to an intentionally curated Accessory Set.

similar fleece jacket | similar tank (m) | joggers (m) | Sunglasses | Belt Bag | Sneakers

Madewell cashmere sweater (s) | similar jeans | Sunglasses | Belt Bag | Sneakers

Long Live Fleece Jackets – Here Are My Favs