Guide To Rocking Men’s Oversized Shirts And T-Shirts In Singapore

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how to style oversized shirts for guys
(Credits: bn_sj2013 / instagram, jichangwook / instagram)

Believe it or not, oversized shirts are back in trend and are a versatile choice for every occasion. They are stylish on just about everyone including famous Korean actors Park Seo Joon and Ji Chang Wook (pictured above). Want to know how to style oversized shirts? Read on as we share some tips and tricks for choosing the perfect oversized shirt! 

3 tips to make oversized shirts work for you

Before you hop onto this fashion trend, here are some fashion pro-tips to help you choose the perfect oversized fit. 

Add Balance

  • Pair your oversized shirts and T-shirts with slim-fit bottoms to balance the look

Buy oversized, not big

  • Stick to the shirt size you normally wear instead of sizing up. Otherwise, you’ll end up with a shirt that looks baggy or a slim-fit T-shirt that’s way too long and narrow –– neither of which is the vibe we’re going for

Take note of these keywords 

  • Keep an eye out for words like “boxy cut”, “relaxed fit” or “oversized” in the description when shopping for oversized shirts or T-shirts

Now that you’re aware of what to look out for when styling oversized shirts, here are five oversized shirt outfit ideas to help you get started! 

1. The classic casual

classic casual outfit how to style oversize shirt for guys
(Credits: Levi’s Official Store, Converse Official Store)

Want to know how to style an oversized shirt or T-shirt that’s suitable for everyday wear? Simply put together an oversized Levi’s graphic T-shirt, a pair of Levi’s slim tapered fit denim jeans (both available on Levi’s Official Store) and a pair of white Converse sneakers (available on Converse Official Store) that can never go wrong! For days you’re in the office or school lecture theatres, simply throw on this Levi’s oversized denim jacket (available on Levi’s Official Store) for an elevated look! If you’re wondering how to wear oversized T-shirts for guys, try out this versatile outfit that’s suitable for every occasion! 

2. The hipster hypebeast 

hipster hypebeast outfit how to style oversize shirt guys
(Credit: Fila Official Store)

Achieve the latest streetwear look with this oversized outfit featuring a white drop shoulder Fila T-shirt, a pair of Fila cargo shorts and a pair of Fila chunky sneakers (all available on Fila Official Store). If you’re wary of the oversized T-shirt looking baggy, fret not, the pair of cargo shorts will complement the top by giving it a more structured look. To further enhance this outfit, simply top it off with a Fila label bucket hat and a Fila multi pocket crossbody bag (both available on Fila Official Store) that’ll sit comfortably across your chest! Still have no clue how to wear oversized T-shirts for guys? This hipster outfit will definitely give you a cool and refreshing new look!

3. The Korean Oppa

korean oppa outfit how to style oversized shirts for guys
(Credits: Levi’s Official Store, Dockers Singapore Official Store, Converse Official Store, Focus Bag.sg, samjune.sg)

Wondering how to style oversized shirts to achieve your Korean Oppa look? This trendy  Korean Oppa outfit features a Levi’s oversized striped button down shirt (available on Levi’s Official Store) and a pair of white skinny pants (available on Dockers Singapore Official Store). To add contrast to the white pants and give it a more Korean vibe, we recommend styling this outfit with a pair of classic black Converse One Star sneakers (available on Converse Official Store) and a black shoulder tote bag (available on Focus Bag.sg). Don’t forget about the signature gold frame glasses (available on samjune.sg) and if you prefer, an Oppa Korean hairstyle for a complete transformation! 

4. The bold and adventurous

bold and adventurous how to style oversize shirt guys
(Credits: Levi’s Official Store, The North Face Official Store, NoTag Official Store, Timberland Official Store)

It can be challenging when figuring out how to style oversized shirts for men. Nail it with this bold and adventurous outfit that features a Levi’s oversized safari shirt and a pair of Levi’s Super Mario denim bermudas (both available on Levi’s Official Store) for a cool, trendy vibe. Pair it together with a pair of backstrap sandals (available on Timberland Official Store) and a mustard brimmer hat (available on The North Face Official Store), and keep cool from the sweltering heat in Singapore. Complete this outfit with a mustard Rawrow square 2way original bag  (available on NoTag Official Store) that’s spacious enough to slide in your personal laptop and other belongings! Still unsure how to style oversized shirts for casual weekends? Try out this breezy outfit that is perfect for all your weekend adventures!

5. The stylish smart casual 

stylish smart casual how to style oversize shirt guy
(Credits: Calvin Klein Official Store, Dockers Singapore Official Store, Aldo Singapore Official Store, Fossil Singapore Official Store)

Want to wear oversized shirts for work without looking too casual? Here’s how to style oversized shirts to achieve your desired stylish smart casual look. Style this Calvin Klein graphic print oversized shirt (available on Calvin Klein Official Store) and a pair of  Dockers straight fit black pants (available on Dockers Singapore Official Store) together with a pair of Aldo slip on tassel brown loafers (available on Aldo Singapore Official Store). Tuck your in shirt for a more formal look and tuck it back out when hanging out with your friends after office hours! Accessorise your outfit with a classy Fossil Luther Watch (available on Fossil Singapore Official Store) and simple black Calvin Klein Triple Compartment Backpack (available on Calvin Klein Official Store)

Have you figured out how to style oversized shirts? 

There are so many variations of oversized shirts and ways you can style them to achieve your desired look! We hope this article has given you a headstart on how to wear oversized T-shirts for guys. If you’re looking for shoes to match your oversized shirts with, why not check out these casual shoes for men! Don’t forget to bookmark this roundup of the latest fashion trends for men in Singapore to always stay stylish! 

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