What to Wear on a First Date in Winter

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Tips and hints from the Hound!

First dates are always a nerve-wracking experience!

No matter how many times you’ve been there and how experienced you are, a first date, just like a job interview is bound to be a tense experience.

But you’re still expected to stay completely calm and relaxed and put forth your best, most confident and unflappable self. And if you want to create a good impression, it starts the moment you first see each other.

First impressions are often the last impressions, and so the way you dress is of absolute importance.

If it’s obvious your date does not like your dress sense or the way you look, it’s almost impossible to turn things around from that point on, nervous that you are.

But worry not; we’re here with some good advice to help you on the road to true love, or at least a second date!

And guys, we haven’t forgotten you, check out our suggestions on what you might want to wear on for a first date in winter, at the bottom of the page.

What to wear on a winter date

It’s that time of the year again. That time of the year when you can’t depend on your swinging body to do half the work for you. Because it’s cold outside, you have to find clothes that are both warm and look good.

So, we’ve prepared this guide for you to figure out exactly what to wear if you’re going out with someone the first time this winter.

Let’s start off with a few general tips before we go on to more specific clothing and dressing advice.

Less is more

On a first date, you don’t want to give everything away all at once. When it comes to showing skin, you want to leave something to the imagination. It being winter, you can’t be too revealing in your clothing anyway.  The reason we made this point, is that you shouldn’t look too desperate.

The same principle applies to makeup as well – less is more. You want your makeup to enhance your features, not overwhelm them.

Achieve a casual yet dressy look

Like we said before, you don’t want to look like you’re trying too hard. The vibe that you are going for is the “oh, I just threw this on” or “this old thing? I just had it lying around”.

But on the other hand, you don’t want to look like a bum. You would want your date to think you put in some effort to make yourself look nice.

However, if you know you are going to a fancy restaurant or a Broadway show then you need to dress accordingly for the venue and the event. If you don’t know where you’re going then play it safe and stick with what you are comfortable in.

Wear what makes you feel good

At the end of the day, you want to project confidence. If you wear something new which you’re uncomfortable in, you’ll keep fidgeting at it all day, which definitely does not exude confidence.

So, make sure you wear what makes you feel comfortable with yourself. If you feel pleasant and comfortable in what you’re wearing it will show and that will always make for a better date and a more fun time.

Now that you have a general guideline on what to do and what to avoid let’s get into a few winter outfits which have stood the test of time and are guaranteed to create a lasting impression on your date.

Tights, a minidress, and a nice jacket

This timeless combination will never go wrong unless you mess up your color scheme. The tights will show off your legs without really revealing anything or exposing them to the cold. The dress serves to show off your curves, and the jacket will protect you from the cold while being a statement in itself.

If the temperature is likely to be freezing then choose thicker wool knit tights or you can wear thicker leggings beneath your outfit too.

If you’re unsure about the color scheme, you can never go wrong with an all-black ensemble. To make it look even more regal and classy, consider adding a long scarf.

Suede jackets with a mini skirt and leggings

Just because it’s winter doesn’t mean you have to put your favorite miniskirt away. A suede jacket with its rugged feel goes perfectly with a denim mini skirt and leggings. Finish off the look with some heels, and you’ve hit the perfect note.

It makes you look casual yet sophisticated – the perfect look for a first date.

If it’s freezing outside, wear parkas or a coat

If it’s really freezing outside or if you’re meeting at an outdoor coffee shop, a parka is a great idea. It shows you are fashion conscious and also a practical person — that’s a good impression to make, isn’t it? Besides nothing stamps out a burning fire of passion like a runny nose and blue lips because you’re freezing cold! And the chances are if you both live in a cold climate you’ll both be used to wrapping up in the cold.

Pair up the parka with a black sweater dress or a button-down mini dress with tights. You must absolutely wear an attractive, dark-colored dress underneath a parka or a coat. You would want to keep the coat or the parka until you absolutely have to button it down because of the cold.

This look is incomplete unless you pair it off with some boots. Both ankle boots and over-the-knee boots work wonders and they’ll keep your feet warm too. Again wear thick knit tights or leggings so your legs are kept as warm as possible.

Faux fur jacket

Now, there are plenty of people who suggest that you stay away from fur as it just looks too expensive. However, we say, if a fur coat reflects your personality go for it and it’s definitely going to pay off dividends if it’s really cold outside. Keep it faux though.

A faux fur jacket and a scarf is the pinnacle of elegance. Just make sure the color of the dress you’re wearing underneath is in tandem with the jacket you’re wearing. You are bound to attract some attention with a faux fur coat, so we would suggest wearing sunglasses as well.

This will give you some amount of privacy if you’re walking down the road.  But we reiterate here, don’t wear a faux fur coat unless you have the personality to back it up.

Guys (we didn’t forget you!)

If you’re a guy, you want to look good without looking like you’re trying too hard. As such, it’s best not to experiment too much and go with a tried-and-tested look that you feel comfortable in.

Our suggestions would be bomber jackets, Levi’s truckers and of course, leather jackets or motorcycle jackets. These jackets have a rugged masculine look and are perfect for a casual first date.

If you want to tone down on the ruggedness, you could always wear a woolen topcoat, or a baseball jacket or a vest, if you’re looking to make things a bit more formal.

Or try pairing a good pair of dark jeans with a pressed shirt and a jacket, this simple look isn’t too rugged and will fit in anywhere without causing any eyebrows to stand if you want to go to a nice restaurant.

If it’s cold out wear a decent parka and gloves to keep your hands warm, if you’re into winter sports it’s fine to wear the jacket and gloves you wear out on the slopes (or wherever). If that’s your personality – let it shine.

Final thoughts

Wear something that isn’t too flashy, risque or bright. Keep it modest, keep it classy and keep it confident. Wear something that is attractive and speaks to who you are as a person. A dress is more than something you’re wearing, it’s a reflection of who you are. So make sure you wear something that makes you feel like the best version of yourself.

A first date isn’t the time for experimenting with a totally new look. Your date wants to get to know the real you, not a version of yourself you think he or she wants to meet. For a relationship to prosper you both have to be honest so don’t hide, be proud of who you are and let that person shine.

If it’s meant to be, it’s meant to be.

Have fun – let’s hope the sparks fly x

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