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The Compass  /  Style  /  How To Wear a Sweater And Dress Shirt/Tie

How To Wear a Sweater And Dress Shirt/Tie

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brown sweater with a blue dress shirt and tie

Master the Sweater and Dress Shirt

Mulder and Scully, Holmes and Watson, Han and Chewy. As independent parts, they could famously exist, but together, their reputation is amplified by the psychological principle of ‘gestalt’, which states that an organized whole is greater than the sum of its parts.

This rings true with the classic fall duo of sweaters and dress shirts. Alone, a dress shirt or sweater certainly can work independently. However, when you pair them together, you form a style powerhouse that takes the best qualities from both.

Psych lesson aside, creating a layered sweater with dress shirt combo will not will not only look good, but keep you warm in those chilly fall and winter months. Here’s how to pull off the shirt sweater combo, from the basics to expert examples.


The Fundamentals:
Sweaters With Dress Shirts

Wearing a dress shirt and sweater may seem easy, but there are some basics that you need to have nailed down before you can even think about donning the combo.


Match the Levels of Formality

dress shirt sticking out of sweater and dress shirt tucked into sweater

Keep Your Shirt Tucked

At your workplace, an interview or on a dinner date, you should always tuck in your dress shirt when wearing one under your sweater. That’s the rule, plain and simple. There are occasions where it may be okay to wear your shirt untucked on its own but once you add a sweater, tuck in the shirt. Trust us on this one. Having shirt tails flapping around below your sweater hem line is simply not a good look for anyone.

Oh — and in case you were wondering…never tuck a sweater into your pants, seriously.


Sweater with Dress Shirts and Ties

sweater with dress shirt collars

When wearing a sweater with a dress shirt, ties are strictly optional. Let the formality of your environment be your guide on whether or not you break out your favorite tie. The easy way to think about this is to ask yourself if you’d be wearing a tie for this occasion if you didn’t opt to add a sweater. If the answer is no, you’re probably okay without one. If, on the other hand, you’re suiting up and a tie is part of the get-up, go ahead and knot away. Just make sure that between your sweater, shirt and tie, you stick to no more than two colors (excluding neutral tones like gray or charcoal).


Make Sure Your Sweater and Dress Shirt Fit

sweater with dress shirt fitting correctly and incorrectly

Even though your shirt will be largely hidden beneath a sweater, it still needs to fit properly. If it’s baggy, you’ll have all sorts of unwanted bunching that will be very visible, especially beneath a thin, snug sweater. Conversely, a baggy, loose-fitting sweater will look equally unflattering. Remember, you’re not gearing up for an Arctic expedition, so keep most of your layers on the thinner side. And bear in mind, you may want to remove a layer once inside, so be sure every layer looks sharp, clean and can stand on its own.


Mix Patterns and Solids Properly

Neutrals

sweater with white dress shirt and a black tie

Pairing two neutral shades is the easiest way to create a conservative look for the workplace. At its simplest, this might be a dark blue V-neck, with a crisp white shirt and a straight black tie. If you want to mix in some more formality, you can throw on a nice carbon gray saxony blazer, and you’ll look confidently cool.


Colors

gray sweater with striped dress shirt and blue tie

Mixing solid colors with patterns is a great way to add a little energy and personality. The shirt may be a variation on the color of the sweater, or the two may be complementary colors. A good example of color matching would be wearing a solid gray sweater with a purple broad striped dress shirt.


Patterns

gray sweater with blue dress shirt pattern and blue tie

When it comes to matching a patterned sweater with a patterned dress shirt, our advice is to refrain from it altogether. The more patterns you add to your look, the more likely you are to create unappealing contrasts that will be hard for eyes to follow. So, ideally, when layering a dress shirt with a sweater, stick with one pattern for the best aesthetic outcome. It can be a striped sweater with a solid shirt or a gingham dress shirt with a solid sweater, either way, you have a clean-and-simple winner.


Match Your Sweater to Your Dress Shirt Collars


The Crew Neck Sweater

sweater with dress shirt thats a crew neck

 Pink Oxford Cloth Dress Shirt by Black Lapel

Your shirt collar points should always be tucked in below the sweater when wearing a crew neck sweater with a tight round neckline. Most popular collar types (including spread, semi-spread and point collars) are all easily kept tucked in unless your sweater neck opening is abnormally large. Of course, a button-down dress shirt collar like that of a classic Oxford will ensure maximum security against slip-ups.


The V-Neck Sweater

sweater with dress shirt thats a vneck

 Blue Custom Dress Shirt by Black Lapel

When pairing a dress shirt with a V-neck sweater, keep triangles in mind. Traditional collars like a point collar or semi-spread will be able to rest nicely against a V-neck sweater, requiring little effort to keep them tucked in. A V-neck sweater also provides the perfect space for a tie, in keeping with the triangular motif so if the formality of where you’ll be wearing said outfit calls for one, a V-neck sweater is a good bet. But keep the tie on the slimmer side to avoid unsightly bulkiness beneath the sweater.


The Cardigan Sweater

cardigan sweater with dress shirt

 Navy Gingham Broadcloth Custom Dress Shirt by Black Lapel

Whether zipped or buttoned down, the deeper neck opening of a cardigan sweater offers the most flexibility. Because you’re able to see more of the shirt, this is where a patterned shirt would work best when pairing up with a sweater. Further, because many cardigans are solid colors, you’ll want to create contrast. A nice navy gingham broadcloth, with or without a tie, works with almost any color sweater — more on colors and patterns later.


The Shawl Cardigan Sweater

shawl sweater with dress shirt

 Purple Broad Striped Custom Dress Shirt by Black Lapel

With its big, full collar, a button-down shawl cardigan sweater is actually a great alternative for a blazer in a casual workplace (sorry, business-formal men, this isn’t for you). Shawl sweaters allow you a lot of room to maneuver when choosing your dress shirt collar, however, we would advise you to stay away from cutaways as it will stand out too much against the broad, shawl neckline. Adding a tie is even easier, just follow our color rules and keep it tucked underneath your sweater. Boom.


The Turtleneck Sweater

turtleneck sweater with blue blazer

 Gray Windowpane Custom Blazer by Black Lapel

This is sort of a “non-applicable” category, but we dig turtlenecks so we had to give it some love, even if you can’t actually wear them with dress shirts. With a suit, or just jeans and a nice blazer, a turtleneck sweater is a great way to create a whole new look. Remember to create contrast; a navy blue suit looks great with a light grey turtleneck, whereas a gray fresco windowpane suit will work beautifully with a deep burgundy sweater. If you want to learn more about this masterful look, we wrote a whole story about wearing a turtleneck properly.


Layered Up

gray sweater with dress shirt and coffee

Fall might be knocking at the door, but now that you know how to layer up with a sweater and dress shirt properly, you should have no fears. All that’s left to do is pick your favorite sweater and dress shirt, and rock your new warmed-up style.

Do you have any layering questions that we can help unravel? Drop a comment below and we’ll get back to you!


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