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A Gentleman’s Guide to First Date Outfits

By ubermen

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First dates are crucial for the development of a relationship. If they’re good, there is a chance for a second, and third date and so on. If they’re bad, well, let’s just say, we’re never going to find out what might have been. We don’t want to imply that the success of a date will depend solely on your clothes, but that is an important factor, too. It takes a person only 7 seconds to make an impression about you, so you should make every second counts and blow that girl away. If you’re stuck for ideas, we’ve prepared a fail-proof guide for the best first date outfits.


Different Types of Dates

Not all dates are the same, and therefore not all dates require the same type of clothing. What you’ll be wearing will depend on the date spot. Some of the most common choices for the first date are coffee shops, bars and restaurants, where the first and the second options call for casual or smart casual outfits and the third calls a more formal wear. The time of the day can also set the tone for your outfit. Dates in restaurants and bars often take place in the evenings, while dates in coffee shops, parks, etc. happen during the day.


Formal Dates

If you are taking your date on a dinner in a restaurant, a night at the opera or some other formal event, you will have to dress appropriately. In most of the cases, first dates will not require a black-tie dress code (but if yours does, kudos to you, you’re a true gentleman), but when they do, a navy or a pinstripe black suit is always a good choice. If the event/place is semi-formal, you can get away with a light coloured or checked shirt, chino pants and a light blue blazer. You can’t go wrong with oxford shoes or derby shoes. Keep your accessories game on top with a leather belt and wrist watch.

Dressy Casual Dates

Some dates are located on the thin line between formal and casual, and those usually include a lunch in a fancy restaurant, cocktail night at a bar, jazz bars, seating concerts, etc. A dressy casual date means that you should search for smart casual outfits such as a tailored blazer and fitted jeans, a slim-fit roll neck jumper and trousers, a Cuban collar shirt and chino pants, etc. As for the shoes, casual leather (brown or black) ones are always a safe bet, but you can also try with dress boots or dapper lace-up boots.


Casual Dates

Most first dates take place at casual locations during daytime or early in the evening, because that way people feel more relaxed and willing to share. Still, sometimes a rock concert or a night out in the club is also a possible scenario. For a more laid-back daytime date, you should wear slim fit jeans, a t-shirt and a blazer or cardigan. You can achieve a similar effect with a simple checked shirt and jeans. Complement the outfit with casual shoes, like white trainers, leather tan slip-on loafers, desert boots, chukkas, or boat shoes. If you are taking your date to a rock concert or a club, opt for similar outfits, yet solid colours. Don’t forget a jacket and a statement leather bracelet to show off your edginess.

General Guidelines

You can dress up in your finest tailored suit and wear the most expensive pair of shoes you have, but if you’re not clean, ironed and well-groomed, all your efforts will be worthless. Get your haircut a week prior to the date (don’t experiment with something new). You should also clip and clean your nails, wear just enough (never too much) cologne, and spray mist. Make sure you put on extra layers of clothes, so if it gets cold as the evening wears on, you can make the classy move of offering her your sweater or jacket.


Remember that your outfit is just one of the factors that will determine the success of your first date. You should do your best to treat a lady as a true gentleman would regardless of where you are taking her, and everything will be fine.





Guest Blogger: Peter Minkoff is a men’s fashion writer at High Street Gent & The Urban Manual magazines from UK and AU. Beside writing he worked as a menswear fashion stylist for many fashion events around UK & AU. Follow Peter on Twitter for more men’s fashion tips.

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