What I’m Wearing: Road Tripping

We’re in Boston this weekend because our oldest is racing in the Head of the Charles Regatta. Yesterday, we made the drive up from Philly.

I wanted to look presentable on the drive, especially since we planned to stop in Connecticut for dinner. Bri was determined for Maddie to try a classic Connecticut lobster roll, and he found a charming spot in Hartford. But I also needed to stay comfortable and pack versatile pieces I could mix and match throughout the weekend.

So, here’s my outfit!

You’ll recognize most of these pieces, but I have to highlight a fabulous new cardigan I found on Amazon. I ordered it in both black with white stripes and white with black stripes.

Let’s break down this comfy yet polished look!

The cardigan is priced at $45 on Amazon, available in sizes XS to XL. I’m wearing a small here, and it’s incredibly soft, feels great on, and fits perfectly. The gold buttons are a standout feature, adding a touch of sophistication—sometimes buttons can make a garment feel cheap, but these are high-quality and really elevate the look.

I’ve layered it over the J.Crew Vintage Jersey Classic-Fit Crewneck T-Shirt. I ordered both a small and a medium and ended up keeping both. The small (pictured) works nicely under sweaters, while the medium gives me a bit more room when I want a looser fit. There’s not a huge difference in the sizes, so if you’re between sizes, I’d recommend going up.

Right now it’s $29.50 plus 30% off at checkout, available in a range of colors in XXS – 3X.

Now, you might be tired of seeing these Old Navy jeans, but I promise I have other pairs! For this weekend though, their fit, wash, and stretch were just right. They were super comfortable for a long car ride, and with sock boots (I packed these from Amazon’s The Drop) and a black sweater, they easily transition into a simple, chic dinner outfit.

I am 5’10 and wearing the jeans in a size 6 regular.

Let’s quickly talk about jean length and sneakers because I get a lot of questions about why straight-leg jeans sometimes feel frumpy with sneakers.

The key is proportion. Notice how these jeans hit right at my ankle? That’s exactly where you want them to fall when you’re wearing a low-profile sneaker like the Veja Campo Bicolor Leather Low-Top Sneakers (which are back in stock in all sizes at Neiman Marcus).

If the jeans were any longer, they’d start to bunch, and that’s not the look you want here. The small flash of ankle creates a light, flattering silhouette.

And yes, I’m wearing no-show socks!

If you’re wondering what to do when it’s colder, just switch things up. A longer jean with boots works perfectly for chilly weather. But for early fall on the East Coast, this outfit is ideal.

I did throw on a coat for dinner, though it’s not pictured. It’s a gray coat I snagged during Amazon Prime Days—super affordable, easy to wear, and highly recommended! It runs a little bit small so I went with a Medium to layer over chunky sweaters.

Finally, I like to keep accessories simple when I travel. I recently picked up these SOJO sunglasses for $15, and they’ve quickly become a go-to, along with these reader-favorite hoops—both from Amazon.