Five Elevated Outfits With High Top Converse

I just recently purchased a pair of black high top Converse after seeing them all over Instagram. They definitely make me feel like a cool mom. I like how they add a little street style to my more classic wardrobe. In this post, I’m showing you five elevated outfits high top Converse.

I do think Converse look super cool dressed down with oversized sweatshirts and graphic tees, but I wanted to show you ways to dress them up just a little. Whether that be a contrasting look with a tailored shirt like a button down or with spring outerwear like a blazer or trench coat. I’m really into these looks!

For sizing reference, Converse run large. I sized down a half size and found that to be perfect, but some people size down a full size. I’m wearing these sunglasses in all these outfits.

Five Outfits With High Top Converse

LOOK ONE: With a blazer and denim

ashley wearing a white tank, black blazer, mid-wash denim, and black high top converse

Tank // Blazer (old from Old Navy; similar) // Denim (take your smaller size) // Converse // Bag (old from Everlane; similar)

I love pairing a black blazer with more casual pieces like these Converse for a trendy but classic look. This blazer was such a good find from Old Navy, but it’s unfortunately sold out. However, I linked a different option at the same price point. Look for one with an oversized, relaxed fit.

LOOK TWO: With a t-shirt dress and denim jacket

ashley wearing a black t-shirt dress, denim jacket, olive green belt bag, and black high top Converse

T-Shirt Dress (old from Madewell; similar) // Denim Jacket (runs a little small) // Converse // Belt Bag (exact color sold out)

Pairing your Converse with a dress is a little more unexpected. You could even pair them with a more feminine dress for even more contrast.

LOOK THREE: With a tee, trench coat, and full length denim

ashley wearing a black graphic tee, tan trench coat, full length mid-wash denim, and black high top Converse

Tee (use code ASHLEYR15 for 15% off) // Trench Coat // Denim // Converse // Bag (old from Everlane; similar)

I’ve been loving the look of Converse with full length denim. Note that I’m 5’3″ and, although these are full length on me, they will be more cropped for someone who is taller. And I’m basically throwing my trench coat over every outfit this spring so no surprise there.

LOOK FOUR: With a white button down and distressed denim

ashley wearing a white button down, distressed denim, ivory baseball cap, and black high top Converse

White Button Down (use code ASHLEY15) // Denim (take your smaller size; they will loosen) // Converse // Baseball Hat // Bag (old from Everlane; similar)

Here is another way to elevate your Converse – with a white button down. I just really like the contrast of a tailored piece with a more casual piece. I added a baseball cap and tote bag for a cool weekend look.

LOOK FIVE: With a black tank, black denim, and a moto jacket

ashley wearing a black tank, black moto jacket, washed black denim, and black high top Converse

Tank // Moto Jacket (old from Levis, similar) // Denim (old from Madewell; similar in the same style) // Converse // Bag (old from Everlane; similar)

And lastly, an all black look always looks elevated and chic, but the Converse and moto jacket give it an edgy vibe. This exact denim is an older pair from Madewell. They are the Perfect Vintage Jean, my favorite style at Madewell. I linked a current version above!

For more spring style, check out this recent posts:

Seven Ways To Style White Denim For Spring
Spring Accessories Capsule
Striped Tops For Spring