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10 Stylish Ways To Wear Converse High Top Sneakers

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Have a pair of high top sneakers that you’re not sure how to style? Check out our guide to 10 easy ways to wear your pair of Converse high tops this season.

A perfect way to dress a casual look is to pair it with high-top sneakers. High-top Converse sneakers are one of the oldest and most classic shoe styles [and Chuck Taylor All Star has been creating the style since 1908].

Converse’s Chuck Taylors’ are sneaker styles that come up above the ankle. They’re usually made of canvas or leather and have thick flat rubber soles, making them dressier than athletic sneakers, so they are a perfect choice to elevate a casual ensemble. These are a closet staple if you need comfortable sneakers for work or days out but still want to look put-together.

If you need inspiration on what to wear with your Converse high tops, well, you’ve come to the right place! We’ve put together 10 outfit ideas for great looks to style with your Converse sneakers.

What To Wear With Converse High-Tops

1. Maxi Dress


Maxi dresses are a good example of an outfit to wear with Converse high tops for a daytime look between formal and casual. The slouchy style of a loose maxi dress complements the sneakers whilst still being put-together enough not to look sloppy [a super important distinction to make when trying to elevate your personal style].

Speaking of personal style, depending on this [and the occasion] the maxi dress style can be switched out. If you’re going out in the evening going for a maxi with a low neck or low back can add a sexy touch. However, if you’re looking to wear this in a corporate environment, you can do no wrong with a broderie anglais maxi.

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Reformation Frankie Silk Dress
Reformation

Frankie Silk Dress

At Reformation

Chanel Resin Chain CC Cuff Black Gold
Chanel

Resin Chain CC Cuff Black Gold

At Fashionphile

Saint Laurent Medium College Shoulder Bag
Saint Laurent

Medium College Shoulder Bag

At Nordstrom

2. Blazer Dress


A huge trend is wearing formal pieces like slacks and blazers for events and occasions outside the work environment, and a great way to dress down a blazer is by pairing a blazer dress [or oversized blazer] with Converse sneakers.

If you’d like to style this for work, pay attention to the neckline and layer with a turtle neck and stockings to keep this chic and appropriate.

An on-trend way to wear this is with a nylon shoulder bag and platform sneakers to add a bit of height, which creates the illusion of longer legs, perfect to show off in a minimal blazer dress.

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Jacquemus Bari Slash Cutout Blazer Mini Dress
Jacquemus

Bari Slash Cutout Blazer Mini Dress

At Neiman Marcus

Prada Re-Edition 2005 Re-Nylon mini bag
Prada

Re-Edition 2005 Re-Nylon Mini Bag

At Prada

Converse Chuck Taylor All Star Run Star Hike High Top Platform Sneaker
Converse

Chuck Taylor All Star Sneakers

At Nordstrom

3. Jeans


It goes without saying a perfect match to sneakers is a bit of casual denim, like a jacket or the perfect pair of jeans. Jeans are an underrated piece of clothing, but often it’s because you haven’t found the best jeans for your body type.Forget sticking to solely black skinny jeans.

If you’re looking for a way to play into trends, the ‘Vanilla Girl’ microtrend consists of outfits in white, cream, and beige tones. So going for white jeans with a pair of classic white Converse could be a great chic outfit. Otherwise, a pair of grey wash jeans with a t-shirt and shoulder bag is the perfect everyday outfit.

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& Other Stories Open-Collar Short Sleeve Sweater
& Other Stories

Open-Collar Short Sleeve Sweater

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Reformation Banyan High Rise Straight Jeans
Reformation

Banyan High Rise Straight Jeans

At Reformation

Prada Re-Nylon mini-bag
Prada

Re-Nylon Mini-bag

At Prada

4. Sweater


If you’re planning a winter look, what better than a sweater to pair with a classic pair of Converse? Sweaters come in all forms, from cashmere collared sweaters to vests to sweater dresses [which are also perfect for layering over dresses for a fun look].

This is a great transitional look for those who live in warmer climates. However, there are insulated Converse available lined with Shearling for the cold months.

If you do live in a warmer climate, a sweater can be perfect for draping over your shoulders or layering with a sundress where the weather gets chilly throughout the evening.

As this is a casual outfit choice, keep the rest of your outfit minimal and understated.

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& Other Stories Knitted Wide Cuff Sweater
& Other Stories

Knitted Wide Cuff Sweater

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Free People Hannah Poplin Dress
Free People

Hannah Poplin Dress

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Comme Des Garçons x Converse Chuck Taylor Hidden Heart High Top Sneaker
Converse

x Comme Des Garçons Sneakers

At Nordstrom

5. Formal Coat


In keeping with the winter theme, a coat and Converse is a match made in styling heaven. For those looking to elevate their style, the best staple is a well-fitting, good-quality coat, either wool or even a trench coat, for those who are lucky enough not to have seriously cold winters.

Because coats can drown out your shape, keep the rest of your outfit fitted and tailored. A super chic way to bear the cold is with layers under [rather than on top]. Invest in some thermals this winter to wear under your pants and sweater, and you’ll likely not need to pile on scarves and hats, which can throw off a put-together look.

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Max Mara Manuela Belted Camel Hair Coat
Max Mara

Manuela Belted Camel Hair Coat

At Neiman Marcus

Reformation Cynthia High Rise Straight Jeans
Reformation

Cynthia High Rise Straight Jeans

At Reformation

Loro Piana Courchevel Cable Baby Cashmere Beanie
Loro Piana

Courchevel Baby Cashmere Beanie

At Nordstrom

6. Blazer


For those who need to dress for the office but don’t have a super strict dress code [sneakers in some environments are a complete no-no], this is the one for you. 

A tailored blazer and well-fitting pants paired with a simple bodysuit and Converse sneakers are a great no-fuss work outfit and can be spruced up with jewelry for after-work drinks.

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L’Academie Camilo Blazer
L’Academie

Camilo Blazer

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& Other Stories Tailored Straight Wide-Leg Trousers
& Other Stories

Tailored Straight Wide-Leg Trousers

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Converse Chuck Taylor Lug Sole Sneaker
Converse

Chuck Taylor Lug Sole Sneaker

At Nordstrom

7. Little White Dress


You know the little black dress, the LWD [little white dress] is its fun summer sister. Like a few of the pieces we’ve mentioned, a classic white cotton dress [whether ‘little’ or not] is an absolute wardrobe must-have and looks beautiful when worn with Converse high tops.

As for the rest of your outfit, keep things simple with minimal jewelry and round-lens sunglasses for a perfect ‘city girl’ summer look.

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For Love & Lemons Jessie Mini Dress
For Love & Lemons

Jessie Mini Dress

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Bottega Veneta Mirrored Metal & Acetate Aviator Sunglasses
Bottega Veneta

Mirrored Metal & Acetate Sunglasses

At Neiman Marcus

Converse Chuck Taylor All Star Sneaker
Converse

Chuck Taylor All Star Sneaker

At Revolve

8. Midi Skirt

Casual leopard print midi skirt outfit with site Converse high top sneakers
via @peexo


If you want to get into midi skirts but can’t find a shoe option that isn’t a sandal or a heel, Converse shoes are the perfect thing to wear. Again, this is a great outfit for work if you have plans with friends or colleagues afterward.

Because midi skirts can drown out your body shape, go for a fitted top such as a form-fitting blouse or body suit.

If you often have plans directly after work, keeping some statement jewelry such as chunky hoops or a cuff in your bag means you’ll always look like you’ve made an effort.

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& Other Stories Flared Crewneck T-Shirt
& Other Stories

Flared Crewneck T-Shirt

At & Other Stories

Reformation Layla Silk Skirt
Reformation

Layla Silk Skirt

At Reformation

Converse Chuck Taylor All Star Sneaker
Converse

Chuck Taylor All Star Sneaker

At Revolve

9. Maxi Skirt


Much like midi’s, maxi skirts are great for the space between formal and casual outfits, though depending on how you go about styling, they can be great for both occasions. It can be dressed down for vacation or summer with a cropped tank or cute camisole, completed by wearing chic Converse high tops.

For an outfit suitable for work, cropped tops often aren’t an option, so a blouse or tee can pair perfectly here. If it’s still not formal enough, or the weather has started getting cold, a fitted blazer works really well.

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Amanda Uprichard X REVOLVE Kenny Blazer
Amanda Uprichard

X REVOLVE Kenny Blazer

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Camila Coelho Lilly Maxi Skirt
Camila Coelho

Lilly Maxi Skirt

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Converse Chuck Taylor All Star Hi Sneaker
Converse

Chuck Taylor All Star Hi Sneakers

At Revolve

10. Two-Piece Set


For the hottest look on our list and the best option, if you’re trying to be a fashion girlie, nothing beats a co-ord set. These are also perfect if you aren’t naturally gifted with the ability to style outfits because the hard work has been done for you!

Two-piece sets come in all forms, from beachwear to going-out outfits, to two-piece suits for office looks. To style the latter, which is always the most difficult outfit to put together, keep your accessories minimal and simple, and let your Converse be the statement piece here.

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Camila Coelho Vanessa Top
Camila Coelho

Vanessa Top

At Revolve

Camila Coelho Vanessa Pant
Camila Coelho

Vanessa Pant

At Revolve

Coach Tabby 18 Pillow Leather Shoulder Bag
COACH

Tabby 18 Pillow Leather Shoulder Bag

At Neiman Marcus

And there you have it! We hope you found our guide on what to wear with Converse high tops helpful. What are your favorite ways to style Converse high tops? Let us know in the comments section!

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