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Shirt Under A Sweater: 21 Ways To Wear This Classic Combination

The ultimate preppy signature move is wearing a shirt under a sweater. Here's how to pull off the combination with style and confidence.

Words by: Ryan Thompson

The corridors of the Ivy League institutions have been a conduit for much of the menswear we continue to see today. Preppy style is having something of a resurgence at the moment thanks to brands such as Aimé Leon Dore redefining how it fits into an urban, streetwear-centric wardrobe.

One of the tenets of traditional preppy styling is the layering of a sweater over a shirt. Soft-collared Oxford cloth button-downs (OCBDs) have always been worn by collegiate types, and on cooler days the simple, functional move to offset lower temperatures was to slip on a sweater over the top.

From classic crew necks to half- and quarter-zips, as well as the once-maligned but now officially cool-again V-neck jumper, luxury fashion brands have re-embraced this studiously stylish duo of garments.

Here’s everything you need to know about how to pair them up and style them out.

Why wear a shirt under a sweater?

This is a look that’s all about the preppy cachet. Yes, on the surface, it’s a nerdy set-up, but if you style it correctly with contemporary accessories, you can create a cohesive and individual look.

Moreover, it’s a great functional layering set-up for fall, when the temperature can fluctuate quite a lot. The sweater is also a sporty foil for the structured formality of the shirt, giving your fit a more dynamic and versatile attitude.

Getting it right depends on your selection of shirt and sweater, but also how you style the rest of your look because it can easily slip into nostalgia territory and you don’t want that.

Follow the rules below to ensure you make the look appear current and original.

How to wear a shirt under a sweater

Don’t overthink the shirt

Man wearing blue denim shirt underneath a white ribbed sweater with white pants

Brunello Cucinelli

Ultimately, the shirt you choose is only going to peep out from the neckline of the sweater and below the hem (if you choose not to tuck it in) so people will only see a sliver of fabric.

That the shirt plays second fiddle to the sweater does not mean it’s immaterial. That sliver still plays a key role in creating a contrast with the sweater.

The shirt collar must create a break in the color of the sweater, hence why a white shirt is always an excellent choice since it will allow the tone of the sweater to pop, as well as draw people’s attention to your face.

A light-tone shirt such as pale blue or pink will do just as good a job at creating contrast in your layers, which is its primary function here.

The collar is key

Man wearing pink soft collar shirt underneath a grey quarter-zip sweater with grey chinos

Hawes & Curtis

With the color of the shirt sorted, the more critical factor to consider is the collar type. This is a preppy look, so large, stiff collars that you would typically wear with a tie are not ideal. Instead, much more preferable would be softly-constructed collar styles that you might typically see on an OCBD.

Stiff collars also tend to stick out above the neckline of the sweater, which is not what you want to see. The collar should be contained within the sweater neckline, creating a neat, smart appeal.

Small tab collars and Grandad collars can be great options, too.

Focus on fine-gauge knits

Man wearing blue jeans with a pink stripe shirt and green textured sweater

Brooks Brothers

Give chunky knitwear a swerve and instead focus on wearing fine-gauge, lightweight knits that you could potentially wear a blazer or suit jacket over.

Texture is great, just not huge chunky cable knits that are going to add excessive bulk. Those kinds of knits work better as outerwear pieces, whereas this look is much more about effective preppy layering.

Fitted styles are ideal for creating office-appropriate looks, whereas more relaxed knits and sweaters are better suited to off-duty ensembles.

Merino wool and cashmere designs are suited to fall and winter, whereas cotton and linen will be more appropriate for the warmer spring and summer months.

Shirt under a crew-neck sweater outfits

Men's light wash blue jeans, white shirt, navy sweater, tan check coat, navy beanie and off-white gum sole high-top sneakers outfit

Alex Mill

Navy and white are a time-honoured pairing that complements each other perfectly.

This casual outfit uses the concept of contrast well, letting the midweight crew neck play the role of the dark canvas, while the peep of white shirt, the flash of the high-tops and the tan check coat are given the limelight.

The jeans match the crew neck with easy tonality, too.

Stone crew-neck sweater with a white shirt and suit trousers

Men's tailored brown pants, white shirt, stone grey ribbed sweater, grey socks and brown leather tassel loafers outfit

Pini Parma

Even though the contrast between the sweater and the shirt is minimal, it still provides a nice tonal accent to play off against the brown tone of the tailored trousers.

The knit is super fine and lightweight, with a nice ribbed texture, making it a great option to wear with tailoring for a sharp contemporary office look.

Cream cable-knit sweater with a pinstripe blue shirt

Men's white jeans, blue pinstripe shirt, camel cable knit sweater and brown leather penny loafers outfit


This looks just screams class. Imagine the cable-knit and white trousers on their own – complementary for sure, but they miss something.

The addition of the blue pinstripe shirt is the magic here, turning a collection of really nice items into a cohesive and sophisticated outfit.

Grey cable-knit sweater with a sky-blue shirt

Men's navy pants, light blue shirt, grey cable knit sweater and brown leather penny loafers with no socks outfit


As with the previous look, it’s the sliver of blue shirt that brings the knit and tailored trousers together.

It’s important to note that even though the crew neck features a cable knit, it is still lightweight and not all chunky, so you could throw over a suit jacket with this look and still feel comfortable.

Grey crew-neck collegiate sweater with a white shirt

Men's navy chino shorts, sky blue shirt, grey collegiate sweater and white sneakers outfit


Preppy as you like, this outfit combines the sporty heritage of a collegiate sweatshirt with a laid-back combination of shirt and shorts.

It’s an easy off-duty look that you can wear in the summer months, while you could swap out the shorts for navy pleated chinos if you wanted a slightly dressier aesthetic.

Toffee crew-neck sweater with a white shirt

Men's light wash jeans, white shirt, tan sweater, tweed check blazer and suede loafers outfit

Todd Snyder

This look is all about the tonality of the toffee tones in the knit, suede loafers and check sports coat, which are crisply offset by the peep of white shirt and the blue of the denim jeans.

Comfortable, casual and superbly put together, it’s elevated without appearing try hard.

Blue midweight crew-neck sweater with a white shirt

Men's wide leg khaki pants, white shirt, black crew neck sweater, green overcoat and sneakers outfit

Todd Snyder

We love the combination of textures and tones going on in this look. Navy and white up top – a failsafe colour duo – combined with the green boucle jacket and the khaki pants all make for a modern and sophisticated casual aesthetic.

Note how the big silhouette of the jacket is complemented by the loose cut of the trousers. Top marks.

Shirt under a V-neck sweater outfits

Grey V-neck sweater with a plaid shirt

Men's white pants, grey checked shirt, grey merino wool V-neck sweater and brown suede boots outfit


Usually, when pairing sweaters and shirts, it’s the former that brings the tone and texture, but in this case the roles are reversed.

A plain grey V-neck is brought to life by the colorful plaid shirt. Given both are quite muted, choosing white jeans is a smart option, giving the shirt and sweater combo a crisp bright background to riff off.

Beige V-neck sweater with a white shirt

Men's grey chinos, white shirt, beige merino V-neck sweater and white sneakers outfit with no socks


This look takes a minimalist approach, using subtle changes in texture to enhance the different understated colors on show. It would work well in a casual office environment.

The muted nature of the look would also serve as a good canvas to accommodate a strong outerwear silhouette such as a belted trench coat.

Oxblood V-neck sweater with a tonal pink shirt

Men's navy tailored pants, pink shirt, burgundy V-neck sweater, navy trench coat and black leather sneakers outfit

Hugo Boss

The ever-so-slightly pinkish hint in the shirt is a good foil for this bold oxblood red V-neck sweater.

It works as a business-casual ensemble thanks to the navy tailored trousers but you could make it more off-duty by choosing to wear white denim jeans.

Charcoal grey V-neck sweater with a white shirt

Men's navy chinos, white shirt, charcoal V-neck merino sweater and brown suede shoes outfit


All of the modern business-casual foundations are in effect here, with a muted palette of grey and navy given a lift by the slice of white shirt collar, and a touch of textural help in the suede boots.

Simple, yet effective.

Grey V-neck sweater with a white shirt

Men's navy chinos, white shirt, grey V-neck merino sweater and white sneakers outfit


The key to this simple, elegant set-up is the fact that it is bookended by the white in the shirt and the shoes.

This topping and tailing of the sweater and trousers creates an easy-to-wear cohesive look. All it’s missing is a tonal blue top coat in textured wool.

Men's beige tailored pants, white shirt, navy V-neck sweater and brown leather penny loafers outfit


Elegance needn’t be complicated. This ensemble shouts money, but you could pull this together on a budget.

The slightly oversized collar gives the outfit a more formal appeal, accentuated by the trousers and loafers.

Teal V-neck sweater with a white shirt

Men's grey pants, white shirt, teal V-neck sweater, brown suede penny loafers and leather brown weekender bag

Luca Faloni

Teal is a fantastic fall color but needs a white dance partner to set it off, hence why the white shirt here is really important.

It can be a difficult tone to pair with other colors, so stick with neutral tones to get the most out of it.

Shirt under a half/quarter-zip sweater outfits

Men's light wash blue jeans, white shirt, navy half-zip sweater and white gum sole sneakers outfit


Worn with slightly cropped jeans, this navy half-zip with a white shirt is the perfect balance of modernity and preppiness.

Relaxed and effortless, as all good casualwear fits should be.

Green quarter-zip sweater with a white shirt

Men's khaki pants, white shirt, green quarter-zip sweater, navy vest and white sneakers outfit

Hawes & Curtis

The fitted silhouette of this green quarter-zip gives this ensemble a slightly more refined look, while still being preppy thanks to the khaki beige chinos.

The addition of the quilted vest lends it a modern touch.

Men's khaki pants, light blue shirt, navy half-zip sweater and brown suede shoes outfit


This aesthetic is the very definition of smart-casual and could be worn in many different scenarios. As it is, it’s an elevated take on casualwear, but add a sports coat or blazer and the look becomes instantly more refined.

Sky blue quarter-zip sweater with a pale blue shirt

Men's navy pants, light blue shirt, pale blue quarter-zip sweater and black shoes outfit


We’re big fans of tonal looks, so there’s plenty to love about this trio of blues.

The interplay between the sky blue of the sweater, the pale blue of the shirt and the navy blue of the trousers is easy and unforced, and is afforded a smart finish with the black leather shoes.

Royal blue quarter-zip fleece with a white polo shirt

Men's black pants, white shirt, royal blue quarter-zip sweater and white sneakers outfit

Crew Clothing

This look riffs on collegiate nostalgia, thanks to that bold blue quarter-zip fleece paired with a white polo shirt.

You could equally opt for khaki chinos or cargo pants if you wanted a more weekend aesthetic.

Burgundy quarter-zip sweater with a white shirt

Men's khaki chinos, white shirt, burgundy half zip sweater and brown suede shoes outfit

Charles Tyrwhitt

The burgundy tone creates a really strong contrast with the accent of white shirt coming through the quarter zip.

Down below, the neutral-tone trousers are understated and tapered to create a sleek silhouette, but it’s the tan suede Derbies that bring the texture to the party.

Men's grey chinos, green shirt, blue zip neck sweater and brown suede Derby shoes outfit

Luca Faloni

A great look if your office is OK with dress-down Fridays, this combination of navy quarter-zip sweater and blue shirt ensures your colour palette remains professional without being boring.

Again, the details matter, in this case the shot of texture that the chocolate brown suede shoes introduce.

When to wear a shirt under a sweater

The versatility of this look, combined with the diversity of options at your disposal, makes it adaptable for all scenarios. Fine-gauge lightweight knits are perfectly stylish over a shirt in the office, and/or worn with a suit, while more textural knits can be nicely integrated into your off-duty fits, with a contemporary shirt.

Half-zip and quarter-zip sweaters are naturally more sporty and lend some authenticity to the preppy aesthetic, while V-neck sweaters can be really diverse depending on the style – for smart business looks keep the v-neck shallow and the knit lightweight, but for a more fashion-forward approach opt for an oversized silhouette with a plunging neck.