24 Best Winter Date Outfit Ideas for Guys Your Girl Will Love

Guys Winter Date Outfits. So you are going on a date in the height of winter and you want to look amazing and yet keep warm, a dilemma for both guys and girls. But what outfits should you wear on a date? How do guys dress on a winter date? What shoes are both stylish and appropriate? And what accessories should a man use?

This post brings the guys some great ideas on how to look fashionable and be practical at the same time during this bleak season. For a first date avoid the uptight looking suit. These are reserved for operas, theatre or the most prestigious restaurant in town (Unless of course these are the location of the date). Keep things smart but casual, a simple light shirt under a sweater is acceptable. Don’t be too casual however; T-Shirts with ‘Angry bird’ logos or offensive phrases are a huge no no! You want to impress, not insult or come across like you couldn’t be bothered. Decent trousers are a must during winter and especially on a date. Jeans are a great choice for both of these. They are sturdy, hard wearing, will look great with a shirt and will give the impression that you made an effort. Make sure you choose a suitable coat for your big night. Smart jackets are always a winner or knee length wool coats. Not only will these keep you warm but with give you a sense of sophistication without looking pretentious.

What to Wear on a Winter Date for Men

winter date outfits for guys

The right date outfit is extremely important for giving you the confidence you need. So when getting ready for a winter date, here are some things to keep in mind:

  • Always play your strengths, which means that you need to wear colors and styles that look best on you. Especially if its a first date, you should avoid experimentation and stick with what you feel most comfortable with.
  • It can often seem like jeans are a bit too casual and pants are too over the top. In such scenarios, it is best to add some textures or prints like plaid shirts, textured sweaters or corduroys as they can add some fun element to otherwise monochromatic outfits.
  • Winter is all about layering so make sure to choose appropriate but warm pieces so you can stay comfortable.
  • If you want to make a lasting impression on a date then go for dress boots.
  • Most importantly, be a gentleman and put your phone down to give all your attention to your lady.

↓ 24 – Elegant and Cozy Turtleneck Outfit

If you live in a country where Winters get extremely crisp and chilly, you obviously need something cozy for your date. We suggest that you go for a turtleneck as it is not only date appropriate but also one of the warmest garments. The look comprises of a woolen overcoat that’s worn over a tuxedo blazer, layered over a woolen turtleneck sweater. For the bottoms, black tuxedo pants really helped elevate the style. The accessories were chosen in a black color and it surely is one of the best colors for winter accessories, they include leather gloves and chelsea boots. Also have a look at 20 Best Outfits for Men to Wear on a Date.

how to dress for winter date men


↓ 23 – Dapper Outfit with White Pants

This dapper look consists of a blue blazer, a light blue casual shirt, white pants, and sneakers. It’s a pretty simple look and yet looks amazingly stylish. In fact, it is the perfect balance of casual and dressed up which is what we need for dates.

what to wear on winter date men


↓ 22 – Trending Style Winter Date Outfit

If you want to try the latest trend for your winter date, go sockless. This can work with both jeans and pants but for more tips, you should check out this highly recommended guide on 27 Ways for Men to Wear Shoes without Socks.

men winter date outfits


↓ 21 – First Date Winter Outfit for Guys

first date outfit in winter men


first date outfit in winter men

↓ 20 – Casual Weekend Brunch Date Outfit

Weekends are all about being casual so for the weekend brunch, go for this effortlessly laid back and yet stylish look. This winter will be all about suede items so here’s a classic suede jacket as they can work in all types of weather, no matter if it’s raining or snowing. And add some suede shoes to top it all off. Don’t miss out these 20 Best First Date Outfit Ideas for Boys to Impress Her.

winter date outfits for men


↓ 19 – How to Dress for a Winter Date after Work

Here’s an outfit that you can wear to work and then go straight to a date after that and still look great. This outfit consists of charcoal grey pants, a classic blue blazer, a denim shirt and a tie.

men winter date outfits


↓ 18 – Winter Dinner Date Attire for Guys

men winter date outfits


men winter date outfits


↓ 17 – Outdoors Winter Date and Photoshoot Outfit

what to wear on a winter date for men


↓ 16 – Lunch Date

winter date outfit for guys


↓ 15 – What to Wear for Coffee Date

how to dress for a winter date men


what to wear for winter date men

↓ 14 – Formal Date Night Outfit

what to wear for a winter date men


↓ 13 – Casual Winter Date Style

For a funky style look try to style it with Funky Jeans for Boys.

↓ 12 – Step by Step Video Tutorial – How to Get Ready for First Date

↓ 11 – Useful Accessories to Have on a Date

During winter, scarves and gloves are not only practical but considered suitable accessories on a date. Choose colors which flatter your look and don’t come over as too overbearing. Darker shades for guys can include navy, burgundy, grey or even black. Scarves are also great for adding extra layers and so will give more shape to an otherwise straight silhouette.
Although hats are an ideal accessory for winter, try to avoid them on a first date. If going to a restaurant you will definitely have to remove your hat and the last thing you want is to uncover messy hair. If you choose to wear a hat it is recommended you take along a small comb.This Dressing style is definitely going to impress your girlfriend and make her fall for you more.


↓ 10 – Perfect Shoes to Wear In Winter For Date

Obviously out in snow, wind and rain the choice of shoe is paramount. It is best to stick to waterproof shoes such as leather ankle boots. These look smart as well as being practical. Avoid fabric footwear such as sneakers and boat shoes these may look great with your outfit but the last thing you want is wet feet on a first date.

On a final note, make sure you are appropriately groomed. Clean fingernails, groomed hair, and brushed teeth are all aspects girls look for. Grubby and shabby is not a good look and although a girl may seem like she hasn’t noticed, she will have and the chances of a second date will dwindle fast! Here are 30 Best Men’s Outfit Ideas to Wear with Monk Strap Shoes.


↓ 9 – Outfit with Jacket

Mens winter date outfits (14)via

↓ 8 – Military Style Long Coat

Mens winter date outfits (13)via

↓ 7 – Street Style Date Outfits

Also see here 18 stylish black men Fashion ideas these days.

Mens winter date outfits (12)via

Matching Beanie hat with Sweater and Bowtie

Mens winter date outfits (11)

↓ 6 – Outfits with Scarves for Winter Dates 

Mens winter date outfits (10)

Mens winter date outfits (9)via

↓ 5 – Short Hairstyle for Date

Mens winter date outfits (8)via

↓ 4 – Guys 1st Date outfit

Mens winter date outfits (7)

Mens winter date outfits (6)via

↓ 3 – Ideal outfit for the Second Date

Mens winter date outfits (5)via

Mens winter date outfits (4)via

↓ 2 – Teen Guy Date Style

Mens winter date outfits (3)via

Mens winter date outfits (2)

Mens winter date outfits (1)via

↓ 1 – Celebrity Winter Date Dress


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