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11 Winter Date Night Outfits Ideas for Men to Try

winter date night outfits cover image

11 Winter Date Night Outfits Ideas for Men to Try

 

Guys, winter is a great time to go out on a date. You’re set as long as you’re covered in all aspects, including clothing. Feel free to look your best as you try to impress people.

I’ve compiled some outfit ideas to help you pick your winter date outfits. So let’s get going right away!

Dressing in Winter Date Night Outfits

As I said, you should go out on dates during winter too. Don’t worry about the cold if you’re dressed appropriately.

But you should look well-dressed for the date. The way you dress speaks volumes about your personality.

It’s a way of expressing yourself in front of your date. Your style, personality, beliefs, and values matter.

If you want to make yourself presentable, your first date night outfits should look impressive too. Your clothing allows you to be confident and look your best self.

Dating and being comfortable in your clothes go hand in hand. You will only be able to enjoy the first date if you’re dressed comfortably. Dress to show your partner you’ve made an effort to look good for them.

Things to Consider for a First Date in Winter

Your winter clothing should match the first date’s venue, time, and activity. Mix and match your winter date night outfits. It’ll help if you’re in no mood for shopping.

Don’t hesitate to go shopping. Try out as many options as possible.

Select an outfit that makes you feel comfortable and warm in winter. Staying warm during winter dates should be your main concern. Also, check out whether you’re entering an open or closed venue.

If you’re shopping online, browse through some of the trendy winter date night outfits. You might get some great ideas on how to dress. You’ll get some fantastic options that look chic and feel warm.

The colour of the dress should suit you and your wardrobe. Also, think about the hairstyle and accessories you’ll wear. Plan everything for your winter date night outfits in advance.

If you lack confidence, pre-date grooming is an option.

Also, keep your date’s preferences in mind while prepping. It might stand you a better chance to impress someone.

Pick a variety of stylish colours and prints. You’ll also find winter boots in many colours, types, and sizes. Most of them will be insulated and waterproof. It will keep your feet safe and protected against the elements.

You want to represent yourself as something other than a desperate person. So make sure you don’t over dress and be as sophistically dressed as possible.

On the other hand, don’t be too underdressed even because that can also give wrong signals to your date that you are disinterested. Groom yourself before going on your first date to capture the heart of your partner.

Outfit Ideas for Winter Date Night Outfits

Guys, your winter date night outfits have lots of variety. Here are some winter date outfits worth trying for guys:

An Oxford shirt for Dinner and Drinks

Oxford shirts are a classic for winter outings. It looks great with a crew neck sweater for a dinner date.

You can accessorize it with a pair of chunky leather boots. You could also wear a tailored overcoat to bring the look together.

Knitwear for Weekend Walks

Outdoor excursions can be fun in winter. You don’t always need to wear your wet-weather gear and wellies.

Look out for knitwear that gives your outfit the extra edge. It’ll look great should you end up in the pub. Layer with bold-coloured basics and strong outerwear for a lasting impression.

Classy Outerwear for a Meeting with the Parents

woollen coat for winter date night outfits

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When you meet your date’s parents, you’ll want to look your best. You can’t go wrong with a classic coat for this occasion. A coat on your winter date night outfits can increase the outfit’s charm.

If you’re going in for a statement coat, keep the rest of your outfit simple. It would blend well with neutral shades.

Play to your strengths with your clothes and personality. It means that you should wear colours and styles that look best on you. If it’s the first date, avoid experimentation and stick with what’s most comfortable.

If jeans are too casual and pants are over the top, find something else. In such scenarios, it’s best to add textures or prints to your outfits.

Plaid shirts, textured sweaters, or corduroys can add a fun element to otherwise monochromatic outfits.

Winter is all about layering, so choose appropriate but warm pieces. You should also think of comfort while layering. If you want to make a lasting impression, then wear dress boots.

In short, be a gentleman and give all your attention to your date.

Wear Scarves with an open coat

scarf and coat

 

Coats and scarves are winter essentials for ages. And yes, you can wear them together as well. Scarves can be both practical and stylish. The same goes with coats as well. You could consider this combo for your winter date night outfits.

Thick oversized scarves will keep your neck and chest warm. It allows you to keep your overcoat open. It also allows you to flaunt the layers you’ve worn.

Opt for a lighter scarf, too if you want. And remember to pick a scarf that contrasts and complements the rest of your outfit.

If you’re wearing dull colors, opt for a colourful scarf. If you have solid colours, then pick a patterned scarf. Either way, you’ll get many chances to assemble lovely outfits.

Use layering effectively with contrasting colours and textures

Effective layering requires some fashion sense along with simple basics. Try to make each layer different in colour and texture.

A sweater over a shirt is an obvious choice. But try something different, like vests or turtlenecks. You could even pick lighter materials and have as many as 4 or 5 layers.

Leather boots are often perfect for a winter outfit

Leather is another fashionable choice for winter date night outfits. Guys, boots are a must-have throughout the winter season. But if you want to make your boots look great, pick leather.

Leather boots are perfect as accessories for winter date night outfits. A good quality boot can add class and style to an otherwise generic outfit.

If the weather’s supposed to be wet, remember to wear waterproof boots. You can also waterproof it with good-quality boot oil or a fresh coat of wax.

Bomber Jackets

Bomber jackets are another stylish outerwear option for men. You can layer them over your winter date night outfits.

It can offer a versatile look with added comfort.

Bomber jackets are a casual staple for any winter wardrobe. This larger style of jacket will keep you warm during the cooler season. Layer it up, or keep it simple for the date.

Cardigans

man in a cardigan for winter date night outfits

Cardigans can be your casual and formal layers for winter date night outfits. With so many different cardigan options, it can be tricky to match them with outfits. But here are some worthy options that you must try.

The long-line cardigan is ideal along with a plain tee and skinny jeans.

The button-up cardigan with smaller-sized buttons is great for a dressier ensemble. You can pair it with trousers and formal shoes.

The shawl neck cardigan is suited for more casual attire. So you can match plain tees, denim jeans, and sneakers. It adds texture and flair to casual winter date night outfits.

Jeans and Flannel Shirts

Jeans are among the most versatile pieces of clothing a guy can have. Whether you prefer slim-fit or relaxed-fit, there’s something for every body type. Denim jeans for men come in many attractive shades and hues.

The washes range from light to dark and complement any shirt.

As for shirts, you must consider flannel shirts to go with denims. Flannel shirts are an excellent choice to pair with jeans.

You can layer them over turtlenecks for plenty of warmth. You could also wear them over a T-shirt for warmth. The latter combo would be ideal for a more casual look.

Guys can also wear flannels without anything but an undershirt underneath. Look for undershirts made from light, breathable cotton for comfort.

Cargo Pants and Long-Sleeve Tees

Here’s another interesting for a guy’s winter date night outfits. Cargo pants are an excellent pick for your winter date outfits.

It’s something different from jeans or trousers.

These pants have a semi-dressy look and vibe to them. They’re available in versatile colours like khaki and charcoal.

They come with many pockets to carry small items. Also, they’re always in style. You’ll find cargo pants with different fits as well. But, a classic or relaxed fit tends to fit well with almost any shirt style.

The long-sleeved tee is a wardrobe staple for men in winter. There are solid-colour long-sleeved T-shirts and graphic tees with eye-catching prints too.

If you want to keep the casual vibe alive. Try them out. Wear them on their own or under an unbuttoned flannel or button-down shirt.

There are many other exciting ways to wear T-shirts and cargo pants. It depends on whether you’re looking for an understated look or bright colours.

Dress Pants and Sweaters

sweater and dress pants as winter date outfits

 

This outfit would suit an office environment. For office or formal events, consider dress pants. It adds all the elegance and class you need for your winter date outfits.

Look out for washable wool to allow convenient cleaning. As the name suggests, these pants have the dressy look of wool on them. But they’re a machine-washable fabric blend.

Chino pants are another versatile variety of dress pants to wear to work or a date night.

Sweaters can also add some interest as winter date night outfits. One of the options would be cashmere sweaters.

These sweaters go well with dress pants in winter. They also come in terrific styles and colours.

There are also fabric blends which are easy to clean and lightweight enough to layer. You can wear dress pants with a collared shirt and a turtleneck or v-neck sweater. If that’s not you, layer a sweater vest and top it up with a blazer.

It has the potential to look like a classy winter date outfit. You can also pair a chunky knit cotton or woollen sweater with corduroy pants. These two options are worth trying as winter date night outfits.

Two Essentials to Include in Winter Date Outfits

Classy Outerwear

Outerwear is very crucial for warmth and good looks. Wear them in a way that keeps you warm throughout the day. But don’t look to compromise on the style front.

Coats and jackets are fantastic additions to a winter wardrobe. You also get all kinds of coats and jackets in the winter market.

Puffer jackets, trench coats, leather jackets, and there’s much more. As always, look at your wardrobe and see what suits your outfits.

You can use them for practical and statement winter date night outfits. Whatever you pick, ensure that it’s winter-appropriate/

Essential and Stylish Winter Accessories

man in a beanie and sweater

 

Accessories are also essential in this process. Some winter essentials can accompany your winter date night outfits. Ensure to look out for the right colours and sizes.

You could go in for beanies, gloves, scarves, or even sunglasses. Don’t forget about winter accessories when shopping for your winter date night outfits, though.

It allows you to add that extra layer of warmth to your extremities. Along with this, it can enhance the look of your winter date outfits.

Conclusion

Winter date outfits can add fun to your special day in the cold. All you need to do is ensure you’re well-dressed for the occasion and the date. You have many options to choose from. So feel free to play around with your winter date night outfits.

If you’re a beginner, you should stick to what works best. I hope you have a great time on a winter date this season. Make the most of your time with that someone special.

 

This post was written by Kosha team member – Shawn Mathias

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