This is a modern update on the classic Preppy combination of layering a fitted pullover over an untucked fitted shirt. Remember how fussy and uncomfortable that combination could be? The straightening and pulling. The lumps and bumps. The perpetual creeping up of both tops. Well, this version is a LOT easier to assemble and much more comfortable. Plus it stays put during the day. The beauty lies in combining a boxy button-down shirt with a boxy sweater, which is fashionable thanks to the fluid and oversized trends. 

It is also an ideal way to sport a button-down shirt that doesn’t fit perfectly (too big in the torso, but right on the bust and shoulders). I like the effect best with a white shirt, but choose any colour combination that tickles your fancy.

Here are the components:

Boxy Button-Down Shirt: Ideally you want a shirt that is at least fluid, and not tailored. The roomy fit of the shirt makes the layered combination a lot more comfortable. Leave the shirt untucked. I like the look with the buttons done right up to the top because it’s strict, neat, and trendy. But by all means unbutton the collar if that feels more like your style 

Boxy Sweater: You’re after a pullover that does NOT define the waist. Think slouchy and baggy, like an upscale sweatshirt. I like styles with welts and lengths that aren’t too long, because these details add structure to the slop. Sweaters with high-low hemlines are another option. Scrunch the sleeves for structure, or leave them down if it’s too cold. Button the cuffs of the sleeves and leave them down if the sleeves of the sweater are shorter than the sleeves of the shirt. 

The sweater needn’t showcase the tails of the shirt if the shirt is the same length or shorter than the sweater. But visual shirt tails add a playful element to the look.  

Fluid Bottoms: I vote relaxed skinnies or straight legs, boyfriend jeans, or slouchy trousers, to create a consistently roomy fit throughout the outfit. These boxy tops also work pretty well with tailored bootcuts or trouser jeans and heels. Or feel free to wear a pencil skirt if a sleek bottom is a must. 

Footwear: Wearing tailored and refined footwear is important because it adds structure to the outfit, especially when your jeans and trousers are baggy. Throw in slouchy and chunky footwear and that element of structure disappears. 

Topper: Coats, motos, trench coats, or blazers — wear any topper that works with the outfit. Or leave off the topper if the weather is mild. 

Accessories: Leave off the scarf and the belt because this is a minimalist look. Add a bag, and jewellery, eyewear and watch as desired. 

I was completely off wearing blouses and shirts under knitwear for about a year. But the trendy boxy fit pullover has made me love the combination again, especially with relaxed skinnies or boyfriend jeans, and white Beatle booties. I have worn this formula six times in the last three weeks. I especially like wearing a white shirt under my pale pink, neon pink, Winter white and citron boxy cashmere pullovers. Feels fresh, updated and polished.

Boxy Shirt with Sweater