How to Dress for a First Date: Your Ultimate Guide

It’s surprising how many men fail to dress appropriately for a first date. Clothing covers 90% of your body so it’s essential that you dress to impress when dating women. This ultimate guide will provide you with some top tips on what to wear on a first date. Second dates will become second nature!

Why Dress to Impress on a First Date?

  • Increases physical attraction – Women care about appearances and are attracted to healthy, good looking men. Wearing the correct clothing can help you appear more attractive by highlighting your positive features and lessening your negative ones.
  • Shows respect – Whether she likes your personality or not is out of your control. However you can take the time and effort to look your best. She’ll be spending a lot of time getting ready for your date – the least you can do is return the favour. Looking like you haven’t bothered can come across as arrogant.
  • Increases confidence – When you look your best, you will feel more confident. Make sure your clothing is clean and ironed. Give yourself enough time to prepare and wear clothes that you’re confident in.
  • First impressions count – Your appearance plays an important role in creating a positive first impression. Dress sharp and smile.

Dressing for the Occasion

You asked her out, so it’s your role to come up with something she’ll enjoy. With that in mind, you need to dress appropriately for the occasion. What you’ve got planned will influence the clothing you wear. Here are some specific guidelines:

Casual dates require a relaxed outfit but not an untidy one. Avoid clothes that make it seem like you didn’t put any effort into dressing. Wear something dressy-casual. Plain blue jeans, work clothes and sweatpants look bad. Go for something like dark wash indigo jeans paired with a short sleeved collared shirt or dress shirt and a casual jacket. Wear a casual leather belt with a pair of similarly coloured shoes or boots, and make sure you tuck in your shirt. Below are some ideas:

Reiss Anchor RIGID STRAIGHT FIT JEAN
1971 Reiss straight leg jean in a hard-wearing rigid denim. With contrast yellow stitching, metal hardwear, belt loops and five pockets; this design is finished with a unique overlay on the back pockets. Anchor has been designed and developed by our studios and atelier at the Reiss Building, London.

Reiss Charter FORMAL SHIRT
Reiss Charter is a formal shirt in crisp white cotton. It has a curved hem, notch detail at the cuff and buttons through the front.

Reiss Glider PLAIN SHORT SLEEVE SHIRT
Reiss short sleeve shirt with curved hem and buttons through the front. Glider in white will take your office ensemble to a stylish new level.

Reiss Jericho CLEAN FIELD JACKET
Casual Reiss jacket with funnel neck and utility detailing. In versatile navy, Jericho has storm flap pockets to the front, welt pockets with zip, adjustable tab and button detail cuffs and to the rear; a single vent for movement and adjustable button tabs for extra comfort.

Reiss Albany SUEDE MONK SHOE
Reiss Monk shoe in brown suede and double buckle detail. With a toe cap and subtle stitich detailing, Albany will see you through season after season

Reiss Jenson PLAIN SUITBELT
Reiss plain suit belt. Jenson in a smart and sophisticated shade of brown is a smooth leather classic design with a silver square buckle.

Evening events such as dinner dates and drinks usually require you to wear a jacket. For events that do not expect you to wear a suit, you should opt for a blazer jacket. And don’t worry that you’ll be the only man wearing one – blazer jackets help men look more authoritative and masculine – plus they’re smart. If the date turns out being more casual than expected –you can always take it off.

Reiss Barton B FASHION ONE BUTTON NOTCH BLAZER
Single button grey Reiss blazer with peak lapels and a luxurious full lining. Barton has four internal pockets and three pockets on the front, while the back of the jacket has a single vent for a sleek silhouette. Wear with the Barton trousers as part of a stylish and comtemporary suit.
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Reiss Johnny B ONE BUTTON JACKET
Crisp, navy thin-stripe suit jacket with single button fastening through the front. Johnny has three pockets to the front, small peak lapels, single button cuff and a single vent to the back of the jacket. With a full lining and three internal pockets, this design is not only practical, but stylish to boot. Can be worn with the Johnny trousers to create a sharp suit.

No matter the type of date, always pay attention to your shoes – Whatever the event, women will always notice what’s on your feet – it’s one of the main things she’ll judge you on. Always ensure that your shoes are clean and stylish.

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Reiss Alfrick TOE CAP OXFORD
Black leather Reiss Oxford shoe with toe cap. Made of 100% leather, Alfrick has a slim profile, double stitich toe cap and black laces.

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Reiss Jacobs BROGUE DETAIL SHOE
Reiss Brogue shoe. In classic tan, which will pair perfectly with navy or a neutral palette, Jacobs is a brogue enhanced with wingtip, panelled stitching and punch hole detailing. The shoe has five hole lacing and will be a sophisticated addition to your look.

Be considerate – Tell her a few days before the date what you’ll actually be doing. Your plans will influence her attire as well as yours. Letting her know in advance will help her decide how she should dress. Women hate being improperly dressed for the wrong occasion.

Grooming Tips for a First Date

Grooming basics – If you want her to get close to you then you need to be well groomed. Clipped and clean fingernails, trimmed nose hairs, and hair growing on the back of your neck – get rid of it all. Use a good antiperspirant, moisturise your skin and have a clean shave. If you like having stubble, use a stubble trimmer to tidy and complete your look. Remember to brush your teeth, your tongue and the roof of your mouth before you leave and carry mints around with you on the date – You may look sharp, but bad breath will ruin your chances of a second date.

Hair – Never try anything new with your hair before a first date. This includes the hair on your face as well as the hair on your head. Stick to the grooming routine that’s worked for you in the past. Get a haircut a week before your date and use the same hairdresser you always do.

Cologne – The best parts of your body to apply cologne are areas that give off the most body heat.  Apply cologne to your wrists, your neck and behind your ears. Your body heat activates the cologne; increasing the strength of smell and making it last longer. Wear cologne conservatively. Women like it when you smell nice, but wear too much and you’ll have her gasping for air.

Essential First Date Attire Tips

Designer clothing – If you wear designer clothing then make sure you stay away from clothes that have big brand logos printed everywhere.  You don’t want to look like a walking billboard.

Matching belt and shoes – Make sure the colour of your belt matches the colour of your shoes. Wearing a black belt with brown shoes is a serious wardrobe malfunction.

Wear clothes that fit – Clothes that are too big or too small always look bad. Always wear clothes that fit properly. If you’re not sure when buying them, ask the shop assistant for help.

Less is more – Keep jewellery and other accessories to a minimum.

Never ever wear humorous clothes and accessories – T-shirts with slogans might offend, novelty cufflinks look silly and cartoon ties are just ridiculous.

Stick to neutral colours – You want to be unique but try not to get too trendy and loud. Stick with neutral colours such as navy, black, grey, white and brown.

Dressing on a budget

It’s always worth spending money on classic clothing rather than a piece that will fall in and out of fashion. You’ll get more usage out of a white dress shirt rather than a bright red one with a graphic design printed on the front that you can only wear with one item in your wardrobe. A couple of casual jackets, a few pairs on interchangeable jeans and trousers, combined with 5-6 classic shirts, a few V-neck jumpers and a couple of cardigans can easily make up over 75 outfit combinations.

In Conclusion

Finally, remember that your attire is crucial but only the first step to a successful first date. You need to fill the date with engaging conversation, show manners and have a sense of humour. By dressing sharp, you can forget about your appearance, be more confident and concentrate on the woman you’re dating.

To Your Success in Life!

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