Favorite Way to Style Hi Tops: Think Jackets

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Ok friends. You know I love hi tops about as much as I love overalls. I also know they’re not for everyone, but I think that reason is just because they are a little tricky to style, right? Maybe I love a good fashion challenge so I gravitate towards things I have to really work at to figure out. I don’t know!

What I do know is that I like that hi tops are a bit more unique and a bit tougher than regular sneakers. But I do, however, love them for their comfort. I can keep them on all day long (walking around AND running after Sienna). A few readers have asked about styling hi tops lately. Here’s what I’ve found…

Jacket 1: Comfy Moto Jacket




As with any sneaker, I think the way to make hi tops most interesting and not overly casual is to pair them with a more structured, more interesting element…like a great jacket. Of course, this is a great idea for any casual outfit, but I think it especially helps boost one where hi tops are involved.

For example, something like this moto sweatshirt jacket reads a little more put-together, if you will, than a standard hoodie. As usual, it’s all in the details and the fit.

I also think showing a little ankle is important when sporting hi tops. This time I tried turning the tongue of the shoe down a bit. You can get away with rolling your jeans up or cropping them slightly above the top of the hi top, too.



Tee: Old Billabong – but I love this one even better! Love the color.

Jacket: Old RVCA – I really like this similar knit jacket in a washed blue and black here.

Pants: (similar) Free People High Rise Roller Skinny Or loving these (with moto details and a bit different color on sale!)

Hi Tops: Chuck Taylor All Star Hi Tops (size down 1 size in Chucks -I’m usually an 8 but wear a 7.5)

Bag: Rebecca Minkoff Julian Mini Backpack (sold out) but the Medium Julian Backpack would hold more and be a bit better for everyday.

Jacket 2: Blazer





I love how a blazer finishes a tee and jeans in general, but paired with a hi top this outfit becomes just a bit more unexpected, which is always good in my book. There’s a bit more of an urban vibe and the blazer makes this outfit easily doable for lunch or shopping dates, casual dinners, teacher meetings, etc…when jeans, sneakers and a tee just won’t quite cut it. A cropped trench coat would work well with this look. Or this cropped jacket that I’m totally loving.


Tee: (similar) JCrew Vintage cotton V-neck Tee

Blazer: (similar) Style & Co Knit Blazer or this one is gorgeous, a bit lighter blue.

Jeans: Madewell 9″ High Rise Skinny in Black Sea

Hi Tops: Vans Sk8 Hi Sneaker in Pearl – the pale pink seems to be sold out, but I’m dying over this copper pair and this pale peach pair of Clark’s is also a great choice for spring.

Watch: The Horse

Structured Spring Jackets


Hi Tops


Are you a hi tops fan? How do you like to style them for spring? I’m totally trying them out with gray jeans next. Obvs. #ilovegrayjeans



About Author

Meet Laura! She's a reader turned contributor and we couldn't be happier to have her as part of the team. Her fun, creative style is, as she says, "somewhere between Madewell and Joan Jett" (YES.) and she delivers some mean dressing room selfies so keep an eye out for those. Fun fact? She loves getting her haircut and we love to see what she has up her sleeve.  

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  1. Elizabeth Rafter on

    Love these options! I bought the peachy vans with perforations but haven’t worn them yet, because…Philly weather. But, I can’t wait to try them with a blazer now! Super cute!

  2. Lilith Homer on

    If you live in Cascadia, and you just got a puppy, you owe it to yourself to buy the rubberized Converse high tops – best dogwalking shoes ever. Now you don’t have to choose between waterproof and well padded.

  3. I saw a Mom at the playground here in Amsterdam who had great style with high tops. She had wide leg high rise cropped black pants, pale gold high tops, grey drapey tee, mustard woven scarf, and forest green blazer in something soft looking, not a business crisp look but more artsy velvet or something. It sounds a bit crazy now I write it out but it all worked together so well (which is why I remembered it!).

  4. Would love some suggestions on what pants (or skirts?) to wear with high tops. The skinny jeans look great but I often can’t bring myself to wear them in the hot, humid DC summers.

  5. I’ve always wanted to get Chucks but wasn’t sure how comfortable they are. Would you wear them for all day walking?

    • Laura Jansen on

      I’ve worn them for years. I love them. There’s a short break in period but then they’re super comfy. They don’t have a lot of cushion on the footbed, but I could definitely wear them all day and do. I might not wear them for heavy duty all-day walking, but for regular everyday they’re awesome.

  6. I love those pale pink Vans- can you tell me the exact name of the color? I must find! And do you feel they run true to size? Haven’t owned a pair in years 🙂

    • I’m so sad they’re out of stock! But I think the color was pearl. Yes run true to size. Maybe the tiniest bit small but not a prob unless you like thick socks w them which I don’t.

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