NY Live - How to Style an Oversized Man-Tailored Shirt

The key to how to style oversized button down is all about playing with shape and proportion. So much more than a humble base layer, it can be easily dressed up or down for numerous occasions. Today on New York Live, we show you five different ways on how to wear it:

Oversized Shirt with Blazer

Fitted Cotton Poplin Button Up, $49, Nordstrom.com 

Printed Cuff Linen Blend Blazer, $69.90, zara.com/us 

Linen Wide Leg Pants, $49.90, zara.com/us 

Mix No. 6 Sandals, $49.99, dsw.com

-Wearing an oversized man-tailored shirt with a blazer gives out quite a classy yet laid back appeal.  

-Tuck shirt into pants and layer collar over suit jacket  

-To keep your look aesthetic, wear a similar shade of the color palette, pink is amazing for fall.  

-You can tuck the shirt in and wear a tight belt around your waist to give it a more stylish look.  

-You can wear this outfit for semi-formal occasions or events- smart and casual, yet the blazer lends a more formal vibe.

Oversized Shirt with Bike Shorts

Fitted Cotton Poplin Button Up, $49, Nordstrom.com 

Crinkle Racer Tank, $45.50, wearebloch.com 

Crinkle Shorts, $45.50, wearebloch.com

-When you’re running to the gym/doing errands, the man-tailored shirt is ideal to pair over bike shorts 

-Keeps your gym look elevated and something I wear even when not workout out 

-Keep the workout gear monochromatic and pair with sneakers 

Oversized Shirt with Tennis Skirt – NO COLLAR/KNOT STYLE

Fitted Cotton Poplin Button Up, $49, Nordstrom.com 

Tennis Skirt, $34.95, thehalara.com 

Beverly Hills Pullover, $24.95, forever21.com 

Chuck Taylor Sneakers, $69.99, dsw.com

-For an easy fall outfit / weekend look, tuck in the collar of your shirt and take the tail ends to the bottom 

-Knot them below and roll them up!  

-Tennis skirts are the must-have skirt of the season and love this plaid one 

-Stick to minimalist accessories and pair with sneakers and playful socks

Oversized Shirt- Cropped at Waist with

Fitted Cotton Poplin Button Up, $49, Nordstrom.com 

a.n.a Highest Rise Straight Leg Jean, $14.99, Jcpenney.com 

Slides, $24.99, target.com 

-While wearing an oversized man-tailored shirt out or tucked in works, change up your style by utilizing two fun techniques  Option 1: The Flat Knot – instead of knotting your button down, slide the one end through the first button hole and the other end  through the opposite side  

-Wearing an oversized T-shirt with a blazer gives out quite a classy yet laid back appeal.  

Option 2: Play with proportions by cropping your oversized shirt at the waist  

-Unbutton your shirt from halfway down. Take one side and wrap it around your waist, feeding it through your belt loop and tucking  into your jeans.  

-Repeat on the other side  

Look 5: Oversized Shirt with Sweater Vest

Fitted Cotton Poplin Button Up, $49, Nordstrom.com 

Missguided Sweater Vest, $17.50, asos.com  

Chuck Taylor Sneakers, $69.99, dsw.com

-A fun addition to your man-tailored shirt- one of the hottest trending pieces- the sweater vest!  

-Pop out your collar on the shirt and roll up the sleeves  

-Pair with leather leggings and Chuck Taylor’s!

Brittney Levine