Matchmaking Advice: Virtual Date Styling Tips for Women

Every week at our boutique matchmaking agency, we spend time planning and preparing our elite clients for social distance dates and virtual first dates. Dating during lockdown can be stressful, and it doesn’t have to be; especially when you’re prepared to succeed. Take styling for a virtual date seriously, as a matchmaker; we make sure our clients feel confident before turning their cameras on for the date or meeting. You only get once chance to make a first impression. Why not put your best foot forward and make an effort to leave a positive impression. 

Do you wonder what to wear on your virtual dates? Staying indoors and connecting with others over a video date doesn’t mean you can’t wear your “going out” clothes. It doesn’t mean you can’t have fun with dressing and exploring different looks. Many singles are resorting to online dating and forming relationships digitally. Continue the fun with dressing for dates by rocking your favourite looks! 

The critical points for styling your virtual outfit is to put more effort waist up, although we strongly advise you don’t date in your underwear. Bottoms count too! We say MORE effort because you should still consider what bottoms to wear. Make sure your hair, makeup, nails are all well put together. The effort and energy put into preparing for your first virtual date should be the same as in-person. 

Need a little inspiration? 

Here are five different outfit ideas and styling tips to help you plan for your first virtual dates:

Timeless Neutrals

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Neutral colours flatter every skin tone—colours like black, white, tan, grey, navy, and brown. Having neutral tone items are the foundation of having an ample working wardrobe for all aspects of your life and not just dating. These timeless colours will help build and mould a great style, no matter what your style is! Tip: Be mindful of what your virtual date environment looks like. You don’t want to blend with the background. Ensure the lighting of your setting is bright so that you and your outfit can shine through that camera. Natural lighting is best.  

Pop of Colour

Matchmaking Tips. Photo credit: @dyleshaxavier

Every woman I’ve ever photographed as a matchmaker will bring out her LBD (little back dress). We all love our black basics and neutral uniform, however, incorporating pops of colour into your virtual date looks can make you stand out. It’ll always be a trend, and you can never go wrong with rocking bright colours. Don’t know what colours to choose? Start with your favourite. What colour do you typically shop for or find yourself dressing in a lot more? If it’s black. That’s ok. You can throw in pops of colours in more settle ways like in your necklace, lipstick or hair accessory. Play around with different colours and have fun with it! 

Classics Forever

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A great way to start building your dating wardrobe is to start with the classics. Classic pieces are timeless, fashionable, and they will never be out of style. Classic pieces are pieces that you have seen over and over again for decades. For women, classics tops include a button-up, a knit sweater, a neutral blazer, leather jacket, or neutral tees. Using a collection of different classic items can create so many different looks because they have so much versatility. Unsure what to wear on your first virtual date? Throw on a white tee and jeans as it is the most classic casual look!

Prints & Patterns

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No matter where you are hosting your virtual date, whether it’ll be from your phone, laptop or computer, the background of your setting can be dull. Incorporating prints and patterns in date night look can make a plain background look extra fab! Avoid horizontal stripes as they can emphasize your top area. Everything else is game. Embrace this form of art, as prints and patterns will always be a fashionable statement.

Last Step: Accessorize

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Matchmaking Advice                Photo credit:

Typically for in-person first dates, you wouldn’t want to wear anything too distracting. Statement pieces can be distracting during the date as your date can’t stop staring at your bold earrings that keep clunking together. For video dates, this is not the case. Play around with all your accessories! Accessories can compliment an outfit and pull the entire look together. For women, these pieces can include hair accessories, pins, eyewear, hats, scarves, and more. Pull out your fall accessory collection and try them on with a different combination of looks. 

A sexy way to spice up your date is to plan your looks together! Ask your date, “where should we pretend we’re going tonight?” If your date tells you that he or she wants to take you to their favourite fine dining restaurant, dress accordingly. Have fun with it! Let your imagination run wild and don’t let this global pandemic ruin your dating fun; what you wear matters. Let your personality and personal style shine and gain confidence in the process. 

If you’d like help with your video date wardrobe or a crash course in video dating, schedule a call with one of our experts today! 

Guest post article is co-written in partnership with Linh Pham, co-founder of Designer Swap and our In House Virtual Stylist and event co-ordinator. 

Linh is Carmelia Ray’s Style Expert.  She consults and advises clients in making fashion decisions for dating and lifestyle photoshoot profiles. She provides customized recommendations on individual pieces, entire looks, color palettes, styles, and fabrics. She is the Co-Founder of an online luxury consignment boutique called Designer Swap and a women’s networking group called Canadian Lady Bosses. She loves fashion, traveling, shopping, and women empowering events.

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