Layering pullovers over shirts is so much more comfortable and easy to pull together in our current fashion era of fluid and oversized fits. The concept of creating a look that is just flattering enough, instead of one that is strictly conventionally flattering, further solidifies the combination as a stylish option. You actually want the layers to be somewhat boxy as opposed to formfitting. 


Layering button-down shirts under roomy pullovers is especially popular this season, and the photos here represent the look well. You do not need a tailored fit for the shirt. Wear it boxy all over for a more current vibe. Layer over a roomy pullover, and allow the tails of the untucked shirt and the cuffs of the sleeves to peek out. Leave the sleeves down or scrunched. Pullovers with neck and side seam zipper detailing look extra fun unzipped because more of the shirt peeks through. It’s also less constricting and therefore more comfortable. 

Roomy cowl neck pullovers and cropped sweaters also look great layered over shirts. Feel free to wear a patterned or denim shirt instead of a solid one. Create a low or high contrast between the layers. Dark solid shirts in black, grey and ink work well too. Wear jeans, trousers, pencil skirts, tweed shorts or even flared skirts on the bottom.

J.Crew Boiled Wool Zip SweaterJ.Crew Merino Wool Asymmetrical Zip Sweater in ColorblockJ.Crew Demylee Giselle Sweater

Banana Republic Chunky Cowl PulloverBanana Republic Textured Zip Neck Pullover

City Chic Sweater


If pullovers aren’t your thing, layer roomy current cardigans over roomy button-down shirts. The photos show both long and short lengths thrown over solid and patterned shirts. Leave the cardigan open to create a vertical line down the front of the body. Pop the collar, leave it lying flat, or tuck it under the neckline of the cardigan. Or button the shirt right up to the top.

Halogen CardiganVelvet Moto Sweater Jacket

Zara Long Cardigan with PocketsC by Bloomingdales Basic Cashmere Cardigan

Soft blouses can be used instead of boxy button-down shirts for a more feminine vibe, and a softer feeling against the skin. Feel free to use collarless blouses and shirts as layers under knitwear if you’re uncomfortable wearing collars. But if you’re after a more boyish integrity, a stiff and crisp cotton shirt in a solid, stripe or plaid is the way to go. 

Here are some street style shots of the layered combination: 

Some of my clients will not wear a boxy button-down shirt on its own, but they will wear one layered under a roomy piece of knitwear because it creates a little more outfit interest. The combination also stretches the outfit possibilities in their wardrobe, and in some instances — if the shirt is very crisp — can add a more polished vibe to the outfit. 

Over to you. Do you layer crisp shirts or soft blouses under knitwear? If this is a combination that you would like to wear, but are struggling to pull together, let’s get you sorted in the comments section.