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Dating Over 50? Three Foolproof Looks To Wear On a First Date

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Finding love the second time around can be daunting. Whether you’ve finally taken the plunge and agreed to that first date or you’re a seasoned pro and have been on the dating circuit for a couple of years, figuring out what to wear can send even the most put-together of women into a spin.

Here, conventional wisdom rings true: stick to pieces that make you feel fabulous and are comfortable–after all, you want to focus on your date rather than nervously tugging at a hemline or sleeve.

We’ve rounded up three ‘dating-over-50’ outfit suggestions that will help you feel confident and sophisticated.

An Evening Dinner Date Outfit 

A dinner date invite can create a tricky, sartorial situation. While you want to look like you’ve made an effort, you don’t want to look as though you’ve over-thought it.

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As a general rule, a simple fitted knee-length sheath dress is a foolproof option. Opt for a slim fit (not super-tight) style with a ruched middle that will help minimize your waist and create a smooth silhouette. Accessorize with a statement necklace or drop earrings and classic heeled pumps as an elegant way to finish off your look.

Just remember the golden style rule; if you’re showing off your legs, keep your chest covered with a high neck design.

Ruched Jersey Sheath Dress, $128,
Ruched Jersey Sheath Dress, $128,
Nine West Finest Platform Evening Pumps, $51.97, Macys
Nine West Finest Platform Evening Pumps, $51.97, Macys

A Casual Coffee Date Outfit 

Grabbing a casual coffee is a popular choice for a first date, whether you’re over 50 or under. After all, there’s no pressure to sit through an entire meal if you don’t hit it off. With that being said, finding the balance between dressy and casual date outfit can be tough.

While you don’t want to look overdressed, you don’t want to look sloppy either. A dark-wash jean is a figure-flattering option and when paired with a colourful or printed blazer, strikes the perfect smart-casual balance. Add a simple plain blouse or shirt underneath and team with ballet pumps and structured bag for a pulled-together look.

ASOS Blazer with Clean Lapel, $44, ASOS
ASOS Blazer with Clean Lapel, $44, ASOS
Lily high waisted jeans, $61.60, Oasis
Lily high waisted jeans, $61.60, Oasis
ASOS LADDER Embellished Pointed Ballets, $45, ASOS
ASOS LADDER Embellished Pointed Ballets, $45, ASOS

A Ballet or Theater Date Outfit

Been invited to the opera, ballet or art exhibition? Pair classic separates for a versatile yet chic look. A knee-skimming, a-line skirt when paired with timeless heels is a sophisticated and (subtly) sexy option. Team with a peach or dusty pink blouse to add warmth to your complexion and layer with a classic trench coat for a feminine look.

Don’t be afraid to inject some personality into your outfit with a pair of colorful heels, statement scarf, eye-catching watch. Small details can reveal a lot about your personality and sense of style.

Pink Soft T Shirt, , $25, Dorothy Perkins
Pink Soft T Shirt, $25, Dorothy Perkins
Jolie Moi Beige Butterfly Print Skirt, $39, Dorothy Perkins
Jolie Moi Beige Butterfly Print Skirt, $39, Dorothy Perkins
ASOS HEART TO HEART Heeled Sandals, $81, ASOS
ASOS HEART TO HEART Heeled Sandals, $81, ASOS


Wednesday 29th of March 2017

Amazing posts for women, It's useful and I’m really enjoyable to read. I will waiting for more articles. thank,


Friday 17th of March 2017

I purchased a dress similar length and although its fitted it has stretch and I am between sizes I kept with the slightly larger size as I am sure it will fit when I loose a bit more and will sit even better this has a little see through detail above the chest area I also went for a short tailored jacket so that will go with other things I want to wear later. Now working on the coffee date outfit. Seen this advice and has helped me a great deal.

Catherine Brock

Monday 20th of March 2017

Thanks for sharing Carol!!

Jen Hoo

Sunday 12th of March 2017

Your post is really inspiring me to take action. Keep up the good work . Thank for sharing!!


Wednesday 8th of March 2017

Well I can agree with your choices. Although, it's hard to know exactly what the older guy will be looking for, your choices are safe for any date


Tuesday 7th of March 2017

Wow, some great options here for the 50+ crowd. A lot of women I go out with in this range seem to have "given up" and aren't really keen on dressing so nicely. Not that it's a big deal but it's always nice to go out with someone that looks absolutely stunning and that also has a wonderful personality. Maybe it's just a problem in North America though because in Europe I find that women 50+ continue to dress quite nicely. Anyways, great suggestions!

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