MUST READ: Great Tips On How To Dress For A Romantic Date

Most men are at sea on what to wear on dates; whether on a first date or otherwise. You do not have to be a style buff to look amazing when going on a romantic date.

Below, are some well thought out tips, to help you look your best on whatever dates you maybe going on in the future.

causal Dates:

Casual dates allow for a relaxed outfit, but that should not be abused. Stay away from clothes that make it seem like you did not put in any effort into dressing – no plain blue jeans, sweat pants, running shoes ( except it is a jogging date). Dark wash jeans, paired with collared shirts, or a dress shirt and sports jacket, are really good combinations for a casual date. Make sure to wear a leather belt, with a pair of similarly coloured leather shoes.

Dinner Dates:

This means you should wear a jacket. For events that do not require a suit, look to a blazer jacket. Refer to my older posts on this Style column, which states how to wear your suits. No matter how informal the date is, pay attention to your shoes. Shoes say a lot about you, so ensure they clean, functional and stylish.

Grooming Tips

1. Make sure to get your hair trimmed, but never try something new with your hair before a date. It is definitely not the right time to experiment.

2. Make sure to wear a nice cologne. Certain colognes can make you more attractive, but make sure it is not overpowering.

3. Make sure to clean fingernails, and trim nose hair, so you come across as tidy.

4. Make sure to shower an hour before you leave.

General Tips

1. Ensure your clothing is interchangeable, so it is easy for you to switch if necessary.

2. Wear a stylish accessory. A stylish detail like a pocket square in your jacket breast pocket, a boutonnière on your lapel, or a quality watch on your wrist, can elevate your style.

3. Focus on looking stylish, not dressing up. The goal is to look snazzy, not to dress up.

4. If you do not feel confident in what you are wearing, do not wear it.

5. Make sure to wear clothes that fit you.


Some people like dating. More power to them. For many of us, it’s a stressful necessary evil made even more disspiriting by a wealth of “meet-your-soul-mate!” screeds that pepper the airwaves. But whether you’re trusting a friend, compatability points, a promising chance meeting or just fate, we all need to go on first dates sometimes, and it’s generally advisable to wear clothes. I polled a lot of friends on this issue and came up with a staggering array of approaches, from “I’ll wear my vintage majorette costume and if he doesn’t like me for me then he’s not worth it anyway!” to “I always buy a new outfit.” Most of us fall somewhere between the two, wanting to look attractive but not trying too hard, hoping to balance expectation with excitement. Here’s what I can tell you for sure:

Wear your magical clothing.

If you have something magical, wear it. You know what I mean: it might be a pair of jeans that’s good luck, or a shirt that makes you look awesome, or just a pair of shoes you associate with something good. Nothing – not the most expensive denim or most artful undies — is a match for something magical when it comes to confidence-boosting.

 Don’t assume you need new clothes.

If you really like wearing something new for a date, I guess go for it. Personally, I’m wary — it puts a lot of pressure on both the date and on you (to find something magic.) That said, if something novel makes you feel good, who am I to object? I am a great believer in new underwear — no, not because “someone might see it”, although, sure – but because you’ll have that sense of specialness conferred by newness, without the pressure. Plus, it’s kind of nice to have Underwear Without History (which has, oddly enough, never been used as an album title.)

I am also in favor of being both a borrower and a lender. Borrowing from a sympathetic friend whose look you like is like having an ally with you — plus, you get the sense of something different without the outlay or the pressure. NB: I am talking about consensual borrowing, not “stealing.”

If you feel like you need something new to give the event sufficient occasion, sometimes splashing out on a little grooming — say, a manicure or (a few days prior) a facial — scratches the itch. It’s a nice confidence boost (or maybe that’s a curly-haired thing, because you never feel like your grooming is completely within your control.)

Be Comfortable.

This should, I hope, go without saying. Painful shoes and jeans that dig into your stomach are not sexy. You want to be able to walk, sit, and eat without thinking about it.

Look Like Yourself.

Another “duh,” maybe, but a first date is not the time to try out a new persona, no matter how cool Brigitte Bardot looked in Contempt.

Bring A Sweater.

You might get cold.Oh, and Practice Sitting Down.
Some things get really low-cut when you’re sitting. This can be awkward. You’ll end up tugging at your neckline. Trust me on this one.

 Have a “Confidence Soundtrack.”

No joke, I have a playlist on my computer entitled “Confidence Dressing.” It’s what I play when I’m feeling shy and apprehensive and need to amp myself up. I always play “I Touch Roses” by Book of Love last, so I feel extra-sassy when I walk out the door.

Now, let’s get down to brass tacks!

I am sure with all the tips I have given, you would definitely become a Style Star at this holiday season!

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