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What To Wear On A Date

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What to wear on a date? As a lady, this is the pivotal question. I don’t want to look too smart, but equally being underdressed would be an embarrassing first impression. I want to look classy and sophisticated, without representing something my grandmother would wear. What we tend to forget is that men have the same problem. Granted I’m sure you don’t spend days and days planning exactly what to wear, but it must cross your mind? If the answer to that question was no, then maybe you need a little guidance. How you dress on the first date really does matter. Your appearance is the first thing she sees when you pick her up (or meet her at the restaurant, if you are not so much of a romantic!). How you dress isn’t the be all and end all, but showing her that you have good taste certainly ticks a few of the right boxes.

A casual date such as the cinema or bowling is a more fun and flirty date and therefore the look you are going for is casual. Wearing a suit with the intention to impress, will only look overdressed and will make your date (who will most likely be wearing jeans) feel very underdressed. I, like many other women like a man in a suit, however equally I love a man to feel just as confident in jeans and converse. Make sure you feel relaxed in your outfit choice; it’s all about comfort. Adding touches like a scarf or rolling up your trousers shows you have style and individuality.


For a dinner date, t-shirt and jeans simply will not suffice. However, throw on a blazer and we’re moving in the right direction. For a dinner date, your date will probably wear a dress, as she wants to impress, and therefore if you turn up in jeans and a tee, she is going to feel very embarrassed. A casual suit works; toned down with a simple grey t-shirt is timeless and uber-stylish. English Heritage is such a huge theme running through many collections this season. The look is so easy to create- it is classic, smart and quintessentially British; perfect for a date. Think knitted polos, chino’s, tweed jackets and striped shirts. Topman and Reiss are perfecting the trend this season.


Meeting for drinks is a little more upscale than a dinner date, and special attention should be paid to your outfit choice. If you’re meeting in a bar, your lady-friend will wear either a dress or a skirt, with the certainty of heels (note: heels give us an added ounce of confidence when we walk). With the bar raised slightly, your trusty jeans should be left at home. To smarten your look, navy or sand chinos work well, a classic striped shirt, brogues and a casual blazer. A casual suit also works well, depending on the kind of bar you are meeting at. A piece of advise gentlemen; it is a common rule amongst ladies, that the shoes men wear are the most important part of the outfit. Women tend to judge a man’s style based on his shoes. Sad I know, but true. Take your time finding the perfect shoe, invest in a couple of good quality stylish pairs, and whatever you wear them with, the outfit will look ten times better.


By Laura Wood

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Paul McGregor
Paul McGregor

Founder of MFM, and short course lecturer at The London College of Fashion teaching all things marketing. Read my personal blog here.



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