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Dating Help: What Should I Wear? - The FreeAndSingle Blog

Dating Help: What Should I Wear?

Dating at breakfast time - what to wear?

‘Fancy a Bagel?’ Breakfast Date

Men

If you’re off to breakfast together, make an effort. To be fair, this goes for every date, but the last thing you want is for her to start her day staring across the table at a bleary eyed, hair-mussed, scraggly shaved example of manhood. Go to bed early, get up on time, shower! Dress in lighter colours but stick to smart silhouettes – ironed trousers, soft shirt, layering jumper. Come prepared to discuss the day ahead.

Women

Obviously, you have to dress for the day in front of you but stick in something special to give a nod to the fact you’re meeting a date first. Make sure you give yourself time in the morning do do your hair and make-up to your satisfaction and wear softer colours than you would in the evening. A white shirt and colourful silk scarf is a fail safe option every women can pull out of the wardrobe to look classy and pulled together early in the morning.

 

Take a date to lunch to get to know them better

 

‘Let’s do Lunch’ Date

Men

It’s lunchtime, your morning passed in a blur, you feel run ragged already. Head to the bathroom! Splash some cold water on your face and wrists, re-apply deodorant and re-style your hair if necessary. If you were super prepared, slip on the spare shirt you brought with you and be fresh as a daisy when you walk into the lunch date. Smart shoes are a must, unless you’re doing street vendor food, in which case have a back-up plan for where to sit if it rains.

Women

Your head is still concentrating on the details for that afternoon meeting and your nervous hair twirling has caused a frizz situation. To the ladies room! A wash of the hands, a spritz of perfume and a bouff up of the hair under the blowdryer serves to have you ready to charm and chat all through lunch. Take a smaller bag with you to keep your focus on your date and not your iphone. Slip a cosy cardigan on to break down the ‘I’m at work’ barriers and help you relax over lunchtime.

 

What to wear to the date you know is breaking up with you

 

‘We Need to Talk’ Break-up Date

Men

If you are about to ditch someone, tone down your look. Dress in sombre colours and at least look like you spent the last few nights in anguish over your decision. If you think you are about to be subjected to the ‘It’s not you, it’s me’ line yourself, dress like you own your own very successful company, have legions of adoring fans awaiting you around every corner and have only to buy a new deodorant to have women swarming all over you. Think smart shoes, fresh haircut, dab of fresh cologne. You’ve already moved on, baby.

Women

If you are about to commence break-up speech number two with your unfortunate date, have the decency to look average, or better, plain. Dark colours, nothing fancy with your hair or make-up, simple clothes. No need to twist the dagger, as it were. However, if you suspect you’re about to get dumped, look fabulous.¬†Accentuate your figure, get a blow dry, wear your favorite lipstick and don some sexy (but walkable) heels. Accept the dumping with a glossy smile, then sashay out of there like you’re off to meet the President for drinks.

 

What to wear for your engagement

 

‘Will you Marry Me’ Date

Men

If you’re getting down on one knee, start off with a good quality, dark trouser – no need to have dirt decorating your knees for the rest of the day, especially as you’re likely to be either wining and dining your new fiancee or else drowning your sorrows in the pub with your mates. Depending on how you plan to pop the question, add a suitable top half of the outfit (polo shirt if active, ironed shirt if dressed up and tee shirt…no, never a tee shirt. Make some¬†effort, please). Make sure you have a jacket with a secure inner pocket, natch.

Women

If you’re the one trying to make an honest man of him, good for you. See above. If you merely suspect that you are about to be proposed to, put some extra effort in. After all, there will likely be photos and these pictures will stick around for the entire rest of your life, so no pressure. Get your hair done before your date, keep your make-up simple and classic – anything trendy will date so fast and have you hiding those pictures within the year. Dress appropriately for the venue and get a French manicure, you know. Just in case.

 

CHECK OUT MORE GREAT ARTICLES ON WHAT TO WEAR: 

More advice on what to wear for a first date

Get some date ideas that nix the classic ‘I have nothing to wear’ wail by their very nature.

Planning your outfit along with your date