The Ultimate Guide to Styling Oversized Shirts

Today I’m going to talk about how to style the oversized shirt, a very, very interesting and common topic. Sometimes I had a hard time imagining how a simple oversized button down shirt could create all sorts of different and good looking outfits. However, the formula is pretty simple. Simply pairing it with leggings or skinny jeans usually gives you a slim and breezy look, and it’s that unique breezy feel that can naturally make you stand out from the crowd. To show you how to style it, I’ve rounded up some of the best oversized shirt outfit ideas for you. Let’s get in right away.

Gray and white striped oversized button down shirt worn over mini denim shorts

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To start this list of casual but awesome outfit ideas, I’m going to give you a little surprise first. To form this outfit, you can wear a really oversized gray and white striped button down shirt as a mini shirt dress. Pair it with black mini denim shorts and white sneakers to look sleek and youthful.

White oversized shirt with black cuffed skinny jeans and converse

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You can look really casual and relaxed with a really oversized white button down shirt. To complete this outfit, you can wear the oversized shirt with cuffed black ripped skinny jeans. Pair these pieces with a pair of classic black and white low top Converse to complete the outfit.

White oversized button down shirt, black skinny jeans and leather ankle boots

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To achieve this boyish and approachable look, you can simply wear a white oversized buttoned boyfriend shirt as a top. Pair it with black skinny jeans and a pair of black leather ankle boots to create this sleek and stylish look. If you want to carry a bag, a leather backpack would be perfect to make you look more youthful.

White super oversize shirt with gray cropped chinos

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Here is a very attractive looking business casual outfit that will make you look confident and relaxed. For a top, you can simply wear a high quality white fitted t-shirt with a white buttoned oversized shirt. Pair them with gray cropped straight leg chinos. Wear a pair of leopard print heels to look grown up and feminine.

Buttoned shirt with heavily ripped blue ripped jeans

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To achieve this casual and boyish look, you can simply wear a white oversized button down shirt as a top. Wear a pair of blue heavily ripped skinny jeans as bottoms to look elegant, stylish and slim. Wear a pair of black leather loafers with studs to add an edgy touch to the outfit.

White big button shirt and gray flowy mini shorts

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This is a very unique outfit that uses flowy shorts instead of skinny jeans. The result is simply amazing. In detail, to achieve this look, you can wear a white oversized button down shirt and a pair of gray flowy mini shorts. Pair them with black stockings and a pair of black leather ankle boots to look super chic.

White baggy long sleeve button down shirt and blue cuffed straight leg jeans

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Here is a very unique and attractive outfit that you can easily grab people’s attention with. Wear a white baggy long sleeve button down oversized shirt and blue cuffed straight leg jeans. A pair of black leather ankle boots and a black choker make this an extremely stylish outfit.

White and gray vertical striped oversized tucked in shirt with blue denim mini skirt

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To achieve this youthful and girly look, you can wear a white and gray button down oversized shirt. The special thing about this outfit is that the shirt is tucked into the pants. Combine the shirt with a blue denim mini shirt with rips. For shoes, wear a pair of crew socks and black pointed toe flats to complete the outfit.

White oversized button down shirt and thigh high boots

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Here is a very interesting oversized white button down shirt. You can pair it with a pair of gray open toe over the knee boots to look cool and relaxed. It is very unique that this shirt is so big and basically worn as a mini shirt dress. You can really stand out from the crowd with this outfit.

Navy blue blazer with slim fit cuffed jeans and white low top sneakers

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To achieve that chic casual outfit that you might want to wear on casual Fridays, you can simply wear a navy blue blazer over a white oversized button down shirt. For the rest of the look, you can wear a pair of blue cuffed slim-fit jeans and a pair of all-white low-top sneakers to complete the outfit in a youthful way.

Oversized light blue button down chambray shirt and black leggings

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To achieve this breezy and approachable look, you can simply wear a light blue buttoned oversized shirt over black leggings. For shoes, a pair of plain, all-white sneakers would look perfect. To look more chic, you can wear a black leather clutch to match the rest of the outfit.

White oversized shirt dress with matching open heels

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To create this demure, sexy cocktail party look, you can wear a white oversized shirt as a mini shirt dress. However, you should wear a pair of very short black or white mini shorts underneath the shirt. For the rest of the look, you can wear a pair of white ankle strap heels and a white clutch bag to look refreshing and elegant.

Light blue oversized shirt dress with buttons and over the knee boots

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To achieve this youthful and chic look, you can wear a light blue chambray button down shirt dress over black mini jean shorts. Pair them with a pair of black over the knee leather heeled boots to look tall, slim and attractive.

Here are the oversized shirt outfit ideas that I want to share with you. They can make you look really airy and natural. Give it a try and be ready to see the more accessible version of you.