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.

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.

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.

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.

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