8 High-Top Sneakers to Style This Fall & Winter

8 High-Top Sneakers to Style This Fall & Winter

High top sneakers are such a fun way to keep your outfits casual and playful. Check out these 8 high-top sneakers to style this fall and winter!

One of the best things about today’s styles is that laid-back doesn’t have to be boring. There are so many ways to casually mix up your outfits without having to be uncomfortable, and high-top sneakers are a great way to make that happen. Plus, they’re more flattering than you think.

The tapered fit of high-top sneakers elongate the legs and create a longer, leaner silhouette.

If you’re nervous about giving this style a go like I was, take a look at these top tips for picking up a pair of high-top sneakers you love. Also included are styling ideas to give you a few options for incorporating them in your wardrobe!

Also check out: A Pleated Plaid Skirt & Comfy Sneakers + 10 Affordable Plaid Skirts for Fall | 6 Low-Key Oversized Jackets to Layer This Fall & Winter | How to Layer a Jean Jacket for a Warm Fall + 5 Tips for Layering Anywhere

**This post contains affiliate links. If you purchase some of the items listed, I get a small percentage at no extra cost to you. I only recommend products I love and use.**

Keep It Classic

Stay classic with a white or black pair of seasoned high-top sneakers. Chuck Taylors have been around since 1917, and are practically as all-American as blue jeans.

Pick a Popular Style

As much as some of us love to hate on trends, trends are a great way to try a new style. Because the item is trendy, you’re likely to feel more comfortable in it as a popular style. It will feel less like a statement piece and allow you to decide if it’s a style you want to adopt and continue to purchase.

Style with a Feminine Dress

Pairing high-top sneakers with a feminine wrap dress is an unlikely match that offsets the girliness of the dress. This combination is perfect for when you want to put effort into what your wearing but want to keep the outfit casual.

Layer & Bundle Up

Sneakers aren’t just for warm weather. High-top sneakers are ideal for the cooler months because they keep your toes and ankles warm. Plus, they’re probably way more comfortable than your ankle boots. You can easily adjust the fit with chunky socks for a warmer fit as well.

With Shorts

The tighter fit around the ankle of most high-top sneakers give the illusion of longer, leaner legs. This works especially well with denim shorts or skirts, when you want your legs to go for miles.

Below is a round-up of some fun high-top sneakers that can easily be styled!

1 Chuck Taylors | 2 Nike Blazer (more size options, more color options) | 3 High-Top Brown Vans | 4 Madewell Sneakers | 5 Gola High Top | 6 Sanctuary Major | 7 Adidas | 8 Green Converse

Top: Urban Outfitters (similar) | Shorts: Target (similar) | Sneakers: Vans | Bag: Farmer’s Market (similar) | Sunnies: Ray Ban | Hat: Urban Outfitters

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