Getting Back into Dating?

It’s been a while since you’ve been out on a date – or perhaps you’re newly single and just thinking about dipping your toes back in the dating waters – either way, you’ll want to make a good impression on your new prospective partner.

When it comes to dressing for dating, there are so many options that you can adapt to your personal sense of style, whether you’re a jeans and t-shirt kind of guy, or a button-down shirt and chinos fella, you don’t have to change your style, you may just need to refine it. 

So, relax, it’ll be fine, as long as you are yourself and don’t look like you’re trying too hard. 

But if you need a little help and a few ideas to try out, here’s our guide to what to wear as you get back to dating.

There’s no point in dressing in a way that doesn’t feel right for your personality. If you’re a Hawaiian shirt kind of guy, please don’t wear stripes or polka dots. Wear something that gives your date a hint about the kind of person you are. If you’re into colour, go wild! Colour blocking looks great, if done stylishly. Maybe you’re into funky hats or shoes, then wear them – but remember to balance your overall look. If you’re going bold with accessories, maybe tone down the shirt and pants. Likewise, if you’re into more tonal dressing, go for it and add some excitement with your accessories. There are so many ways to look stylish, but most importantly, wear what makes you feel like the best version of yourself!

This doesn’t mean you have to look formal, on the contrary, it means wearing what is appropriate and stylish and showing you’ve made an effort to look good. There’s no point wearing a shirt and blazer if you’re planning to go for pizza, but by the same token, if you’re taking your date somewhere a bit special, that worn and daggy t-shirt you love so much, just won’t do. Wear clothes that fit well (no slouchy jeans or sweatpants), look sleek and neat. Maybe you’d look good in a linen shirt and jeans or a comfy sweater and khakis. Try tucking in your shirt and wearing a nice leather belt and leather loafers for an approachable look that’ll still turn heads. What matters most isn’t how much you spent on your clothes, but how well they fit your body.

The activities you’re planning to do on your date are a great starting point for putting together an outfit, so plan ahead and know what you’ll be doing. If you’re going for a romantic walk on the beach, you’ll want to wear pants you can roll up, shoes you can slip off and a jacket you can throw on if it’s cool outside. If you’re grabbing drinks on a hot summer’s night, wear a shirt with sleeves rolled up and lightweight pants that won’t be too constrictive. Sweating profusely over a cocktail is never a good look. 

When it comes to getting back into the dating scene, feeling comfortable is paramount. It’s not worth trying to be trendy for the sake of it, if the clothes you’re wearing are spoiling your date. Given that you’ll likely be feeling pretty nervous as it is, choose clothes that fit well and are right for your body. The last thing you want is to be distracted by uncomfortable clothes that scratch, itch or constrict your movements. 

Chances are your date is going to put a lot of thought into what they wear, so you should too! Most guys who are new to paying attention to style have a pretty limited selection of shirts and pants to choose from in their wardrobe. There is much to be said for having a good basic wardrobe with options to mix and match. But if you’re just getting started on your style journey and need a solid date outfit, you can’t go wrong with a pair of crisp jeans (no holes or distressing and hopefully in neat indigo or black) for a first date. Chinos are also a safe bet as they can be dressed up or down depending on where you’re going. Pair them with a button-down shirt (darker colours are the most flattering) or for a more casual look, an unbuttoned shirt with a tonal t-shirt underneath. If the weather is cool, throw on something like a simple bomber or denim jacket.

DO

1. Take a shower right before getting dressed

2. Make sure your clothes are ironed and stain free.

3. Wear quality underwear (you never know…)

4. Wear a little spritz of cologne (don’t bathe in it)

5. Polish / clean your shoes

DON'T

1. Wear wrinkled or grubby clothes

2. Wear hoodies (shows no effort)

3. Wear hats or sunglasses indoors

4. Forget to brush your teeth

Lastly, (and thank you for reading this far) remember that confidence is key. While an awesome outfit can boost your confidence, your clothes should really be a platform to allow your awesome personality to shine through.