The $50 Shoes That Transformed My Wardrobe for the Better

I basically only wear two shoe silhouettes in my day to day—basic black ankle boots (especially this time of year) and sneakers. While I’ve recently gone over my adoration of the former, I thought I’d take the next few minutes to chat about the latter. But I’m not here to bring you the range of trainers that stock my closet this time. I wanted to focus on one key style, as it’s quite literally the only one I’ve been wearing for the last few months.

Yep, I’m talking about my checkered Vans slip-ons, which have been a staple in my wardrobe arsenal for a few seasons now. Although I’ll be the first to admit that I’m a little late to the game here. This specific Vans style emerged in the ’70s as a staple in Southern California skateboarding culture thanks to the innovative waffle sole (ideal for board grip) and durable, no-fuss sensibilities. Since then, the style has cemented itself as a tried-and-true classic.

First and foremost, I love that they instantly bring a cool, not-trying-too-hard feel to legit any ensemble I’m wearing, whether that’s a jeans-and-sweatshirt situation or a more dressed-up vibe with trousers and a jacket. I’m also into the fact that they’re one of the most comfortable pairs sneakers I've ever worn. I legit just slip them on and go. And, fun fact, it appears other fashion people are on the same page, as I often spot a range of fresh outfits with Vans sneakers whenever I’m scrolling through Instagram.

To give you a little taste of what I mean (and really break down my fondness for the kicks), I rounded up a few inspiring ensembles featuring the timeless slip-ons that upgraded my wardrobe. And naturally, I also shopped out a range of iterations, including other Vans sneakers I’m looking forward to testing out as well.

Voila—here I am in my coveted checkered kicks. I’m wearing the pink iterations here (but I have the classic black-and-white and all-black versions as well).

One of my fellow WWW editors also swears by the must-have sneakers. Here, she complemented a trouser-and-jacket ensemble with the slip-ons.

While this fashion girl could have gone for standard booties with this elevated ’fit, the Vans choice feels even cooler.

If you work in a more casual office settings, try the sneakers with modern jeans and a statement jacket.

Here’s proof that the sneakers really can go with anything—even a sophisticated suit.

You just can’t go wrong with a tee, jeans, and Vans ’fit. It always works.

Make the sneakers the hero of your winter ensembles like this fashion girl, who’s showcasing hers with her slouchy overcoat and skinnies.

Now, shop more Vans slip-ons:

And now shop more Vans:

Next, check out the basic shoes women over 40 will never stop wearing.