How to Dress on a Date Without Looking Like You’re Trying Too Hard

Okay, so you finally asked out the girl of your dreams and it was an astounding success.

She said “yes” and now you’re about to embark on your first date together. When preparing for the date, there are a few things you’ll need to carefully consider. It goes without saying that you should pay adequate attention to what you wear on the date, but it’s also crucial that you don’t come across as though you’re trying too hard. It may sound easy, but it’s important that you get it right. After all, it will help to determine whether she accepts your asking for a second date (assuming you do ask, of course).

It may also sound shallow, but making an effort in what you wear shows her that you respect her, which can lay a strong foundation for what could potentially turn into something more. Men like to put effort into preparing for a date and to make the right first impression, but that doesn’t mean you want to stress over it. Here are a few tips, in various date scenarios, on how to impress your date with your dress sense, without wishing you’d never have bothered in the first place.

The coffee shop date

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This is a great low-key way to get to know someone quickly, without much commitment. If you find that she’s not the hot prospect you thought she was, or if she turns down your offer of a second date, at least you didn’t invest too much by way of funds. That doesn’t mean you can get away without paying careful attention to what you wear, however. There’s nothing wrong with a causal look, but you still need to show her that you care how the date goes by putting in some effort.

You can wear a button-up top, either short or long sleeved. It’s a great way to draw the right kind of attention, especially if it’s in a colour that pops. Dark wash jeans go with plenty of tops and give you that casual look, yet still manage to show off some sense of fashion. Opt for a pair of canvas shoes and you’re all set.

The pub date

If you’ve chosen a venue with a creative and lively atmosphere, you’ll need to have an idea of the kind of people who frequent it. Even a pub with a fun air or classy vibe can have a dressed-down feel, so you don’t want to overdress and feel awkward. Many people who go to pubs do so after a long hard day’s work to unwind, as well as those who just want to go for a quick drink without putting much (or any) thought into what they’re wearing.

A pub can still be a great venue for a date, if it’s the right venue or atmosphere, however. So, while you don’t want to overdress, you very definitely don’t want to look like a slob, either. The right pair of canvas shoes or a pair of top-siders are the obvious options for this look. If you’re feeling confident enough to dress a bit more on the formal side, then by all means, do so. Put on a pair of coloured dress pants or even wear that bow tie.

Whether you met at your favourite nightclub or online, you’ve obviously created an impression that attracted her to you. You don’t want to blow it by turning up as a second-rate version of yourself. If you met online, what impression she already has of you depends on which photographs you chose to upload to your profile, of course. A site like Badoo provides dating insights regarding, not just your profile, but online dating as a whole. While fashion is important, it obviously isn’t everything.

The fine dining date

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If you’re contemplating fine dining your date, the likelihood is that you’re feeling somewhat optimistic. This is the kind of situation where you really need a look to complement the venue. Once you’ve picked the ideal restaurant, now it’s time to show her that your great taste extends to your wardrobe. You can again go for a button-up top, but, this time, you’ll need to wear it with a tie or bowtie.

Pay attention to your choice of tie though. You won’t want to look like you’ve just arrived at your date straight from work. Choose a pattern that’s fun without being garish, and, at the same time, shows off your personality. Complete the top-half look with a sports jacket or blazer. You can then go for a pair of khakis, a pair of smart trousers that match or complement your top, or even black jeans. Go for either dress shoes or top-siders, and socks that draw the right kind of attention. Your date will see that you can look smart and have fun at the same time. If you want to go for a suit, then fine. The only two things to change in this case would be your jacket and pants, so make sure that you choose something that goes with your chosen colour.

The ethnic sit-down date

Showing your date the Thai restaurant that’s always managed to impress you, or that amazing Mexican place everyone raves about, can show her that you’re open to new things. You’ll want to be confident that both the food and service is of a high quality, however, so, if you haven’t visited the venue yourself, be sure to find at least one friend who can recommend it. Dress-wise, here’s where you can have some fun. Choose a cool colour or pattern for your v-neck or button up. You can get away without wearing dress pants unless the rest of your outfit would be incomplete without them. You can finish off the look with canvas shoes, and socks with a fun pattern or colour.

In terms of accessories, socks can be enough to complete your look. If you feel like you want to add a bit more detail, a pocket square or a nice watch would be the way to go. Just keep in mind that the girl you’re taking out may be “the one”. So you’ll want to do your best to create great memories to look back upon and share stories with friends and family in years to come. Dress as if it will work out, and, if it doesn’t, at least you will have adopted some improved dating habits.

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