9 Top-of-the-Line Sneaker Outfits for Fall 2021

Fall is a great time to take a dip into the high-top sneaker market, regardless of whether you are a seasoned sneaker fan or a newbie. Boots are a staple of fall and a wardrobe staple that you will always reach for, especially if they’re high-heeled or knee-high. However, they can be formal, which is why it’s important to avoid them. High-top sneakers are a great choice if you want an effortless look.

Some are sporty, including color-block Nike’s and three-stripe Adidas. Converse All-Stars is another example. High-tops don’t have to be sloppy. Sleek leather silhouettes are the key. Ultra-minimal designs in white and black are a good example. You can also achieve flawless high-top sneakers in fall with nostalgic silhouettes, such as the ’80s or ’90s. This high-top look is especially great with leisurewear, for a Princess Diana fashion moment.

High-top sneakers are a popular fall sneaker trend. Megan Stephens is the senior footwear buyer at Anthropologie. She says they’re also timeless. Stephens states that high-top sneakers are a staple in your wardrobe, and a must-have for any season. They’re the perfect transition piece to your wide-leg trousers into fall. The wide range of styles available in high-tops is what makes them so popular.

You can find nine fashionable high-top sneakers that are perfect for fall, no matter if you’re trying to recreate your childhood style or adding the over-ankle silhouette to your wardrobe. We share our insights and each outfit can be purchased online.

Denim Days

Many people think a pair of jeans with a high-top is the best look for denim. They can be worn either wide-leg, or cropped kick-flare. A white t-shirt and trench are easy to wear when it’s mildly cold. Stephens suggests that cozy high-tops can be worn with straight-leg denim and a chunky sweater to create a more textured look.

Stylists recommend this items:

• Jeffrey Campbell Endorphin High-Top Sneakers – $105
• Agolde Pinch Waist High Rise Kick Jeans – $178
• COS Short Linen Trench Jacket – $150
• Re ona Long Bamboo T-Shirt – $78
• Sezane Diego Jumper – $145
• P448 Star High-Top Sneakers – $298

Leather Weather

Fall is leather weather. What’s better way to show your leather-loving side than with slouchy trousers, high-tops and a unique sweater?

Stylists recommend this items:

• Wilfred Pants that are effortless – $148
• Tibi Aran Cable Knit Cut-Off Sweater – $385
• Nike Sneakers Dunk High – $261
• Vavvoune The Mishe Bag – $495

Do The Diana

Stylist suggests Stephens’ vintage-inspired Athleisure look: “Go all Princess Diana with rock biker shorts and APL Defenders.”

Stylists recommend this items:

• APL TechLoom Defender Sneakers – $325
• Human Nation Gender Inclusion Heathered Organic Cotton Blend Joggers – $68
• Kotn Fitted Turtleneck – $39
• Frankie Shop Isla Single-Button Blazer – $300
• Frame Ritz Hat – $128

Cozy, Elevated

The sweater dress is undoubtedly one of the easiest pieces for fall. Layer leggings under the sweater dress with high-tops and a tailored jacket to make it more interesting.

Stylists recommend this items:

• Anine Bing Shawn Dress – $399
• Adidas Originals Forum 84 Patent-Leather and Smooth High-Top Sneakers – $120
• Skims Cotton Rib Legging – $52
• Massimo Dutti Long Grey Herringbone Wool Coat – $349

Menswear inspired

For fall menswear styling, a boxy jacket, slimming trousers and high-top sneakers are essential. Stylist recommends cropped, wide-leg corduroy trousers and a large button-down.

Stylists recommend this items:

• Superga 2433 W Moleskin Black Multi Sneakers – $90
• Cuyana Linen Double-Breasted Blazer – $275
• Co Pants in Pleated Crop – $795
• JW Pei Gabbi Bag – $95
• Isabel Marant Etoile Charly Herringbone Wool Blazer – $550
• Everlane The Corduroy Wide Legged Pant – $88
• AYR The Deep End – $125
• Veja Nova High-Top Sneakers – $114

Matchy-Matchy

A look that is high-top sneakers and paired with matching separates is visually more striking than one that is low-key. You can go all-out with a matching top, skirt and coat or just a matching sweater set.

Stylists recommend this items:

• Zadig & Voltaire ZV1747 High Flash Sneakers – $328
• YanYan Rosie Rosebud Extra Long Sleeve Cardigan – $425
• YanYan Rosie Rosebud Skirt – $425
• Zara Long Coat Special Edition – $119

Simple Tailoring

Tailoring doesn’t always mean stiff. For a casual, work-to-anywhere outfit, pair wide-leg trousers or flared pants with a stylish hip-length coat and leather high tops.

Stylists recommend this items:

• Jonathan Simkhai Rowen Melton Wool Fringe Lapel Jacket – $595
• Tove Felice Trouser – $250
• Koio Court Coal Distressed Sneaker – $298
• Ree Projects Helene Mini Bag – $595

White Jeans for the Win

White jeans instantly revive any denim fatigue that you might feel throughout the season. For a fall-appropriate look, pair your white jeans with a tonal high top, a button-down shirt and a dark jacket.

Stylists recommend this items:

• CU4TRO Norris Sneakers – $114
• Mother The Looker High Rise Ankle Skinny Fray Hem Jeans – $198

Casual Dress

Stylists recommend pairing high-top sneakers and “mini dresses”, a cropped cardigan and ruffle socks at the top of the season. Or, you can try a seasonally-fitted sweater dress for days when you don’t feel like layering.

Stylists recommend this items:

• Ba&sh Grazie Dress – $310
• Converse Run Star Hike Hi – $110
• Americana Fuzzy Crop Cardigan – $95
• Lele Sadoughi Black Tie Ruffled Sock Set – $45
• Victor Glemaud x Target Long sleeves animal print dress – $55