Sweater Weather Looks for Him | Lands' End

Sweater weather looks for him

Sweater weather. Just the sound of these two rhyming words coupled together is enough to inspire visions of rust-colored fall foliage and post-Thanksgiving pick-up football games.

But as much as we enjoy the sounds of freshly fallen leaves being crushed underfoot and the second helping of pumpkin pie, there’s more to the sweater weather season than nature and family festivities. For starters, there are the looks you’ll be wearing as the sweater weather portion of the calendar plays out in glorious fashion. Follow the guide below to get a full accounting of some of our favorite men’s sweater weather looks.

His jeans-and-a-flannel-shirt look

Yes, there is such a thing as pre-sweater weather season. It’s that bridge between summer and fall when the days are still too balmy for a sweater, but the nights grow cold enough to warrant wearing an extra layer. It’s one of our favorite times of the year, but properly dressing for this shoulder season can be a bit mystifying.

For best results, pick up a men’s flannel shirt and wear it as you would a sweater. When it’s warmer during the daytime, wear it unbuttoned and open over a t-shirt as if it were a men’s cardigan sweater. And when it grows colder in the evening time, button it up for some light insulation.

Naturally, you’ll want to match this flannel shirt to a good pair of men’s jeans. Few things go together in the male closet as well as a cozy flannel shirt and a pair of broken-in denim.

His chinos-and-sweater look

We’ve deliberately kept the description of this look general, as it refers to a whole category of looks rather than a single outfit. As dress codes have become more relaxed in recent decades, suits and even sport coats are becoming a rare sight among offices. To some extent, they’ve been replaced in the business casual dress code by men’s chinos and sweaters.

For a look that’s both cozy yet polished enough for office wear, match a pair of crisp chinos to a button-down shirt and a sweater. If your office tends to lean on the more casual side of things, feel free to select a crewneck sweater. The crewneck sweater stands on the casual end of the sweater spectrum due to its athletic origins and inspiration.

To bring the chinos and sweater look into a slightly more formal territory, choose a V-neck sweater instead. The cut of a men’s V-neck sweater frames the face and highlights the collared portion of the shirt in much the same way that a tie would. You could even wear your finest cashmere sweater to bring an extra, upscale touch to the outfit.

His turtleneck-with-anything look

It’s no secret we’re big fans of the turtleneck. Few other articles of clothing are at once so iconic in appearance and successful at their basic function. And thanks to the turtleneck’s unique heritage–it was first worn by hard-working Irish fishermen and then by sailors in WWII before being adopted by Hollywood celebrities and beatnik intelligentsia–it’s suited to casual and formal looks.

To make the most of its casual appeal, match your turtleneck to a favorite pair of jeans and boots. This look is particularly successful if you choose a turtleneck in a chunkier, heavier knit.

For a look that falls squarely in the middle, pair a finer-gauge turtleneck with a pair of chinos and dress shoes for an instant office look.

But to bring the turtleneck to its dressiest heights, select a fine-gauge turtleneck made of cashmere and wear it under a blue blazer with either chinos or a pair of wool pants.

His dress-shirt-with-a-layered-sweater-and-slacks look

Nothing is more classic than a dress shirt and slacks. In the fall, a dress shirt alone can be a little chilly. So, paid it with a simple sweater for a comfortable yet polished look.

In fact, this is a great look for more formal events or the office. Start with a simple dress shirt in any color, and match it with a v-neck, crewneck, or half zip sweater. You’ll want to go with a dress shirt and sweater that aren’t thick or heavily textured for the layered look to work. Pair them with a pair of brown, black, or navy men's dress pants

To give yourself a polished look, consider wearing a pair of dress shoes. If you’re not a dress shoe sort of person, you might be able to get away with some boots that are mostly hidden under your slacks. This look will not work well with sneakers, though.

Add a neutral belt and a nice watch, and you’ll look amazing!

His classic tee-jeans-and-a-layered-sweater look

Who says you need to stray from a classic go-to? Sometimes it’s a jeans and t-shirt kind of day. If it’s a bit chilly, you can always layer a sweater over the top.

Simply grab a basic shirt (long or short sleeve) and pair it with your favorite pair of jeans. A half-zip sweater will look best with this outfit type since it has a casual feel to it, as well. You can layer other sweaters over the top, but make sure if you do, it’s a crew neck since a v-neck might not look as good with just a plain t-shirt poking out underneath. Complete the outfit with a pair of dress shoes for a more dressed-up look or sneakers for a casual look.

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