Matchmaking Advice: Virtual Styling Tips For Men

Online dating can be difficult, let alone – figuring out what to wear on your virtual dates. As a professional matchmaker working with some of the world’s leading entrepreneurs, executives and business owners, I’ll have men text me photos of their date outfits asking for advice. High-status men understand they must look and act the part to attract a high-quality partner. Dressing for success, and “to impress” is no accident. Dating online and in real life is highly competitive. We coach our matchmaking clients always to show up looking and feeling their best. 

There is an overwhelming amount of tips and trends in fashion, and sometimes it can be challenging figuring out where to begin. If you don’t know what your sense of style is, that’s ok! Discovering your style and signature look to attract the right partner and professional opportunities doesn’t happen overnight. As Carmelia Ray’s stylist, I help clients find a unique style and help you work on your ideal image goals. 

Think about what your image goals and your life goals are. Is it to look well put together? Is it to incorporate more colourful clothing in your wardrobe? Is it to attract high-quality women? Is it to feel more confident during your dates?

Planning what to wear for your video dates requires two things; time and effort. If you are wearing something NOT reflective of your real personality, it’s going to affect your self-esteem and create a false impression with new people you meet. Follow your own rules when it comes to fashion because your style is what makes you unique. If you’re still figuring out what works best for your body type, lifestyle and comfort, consider working with a stylist. You should wear clothing you feel confident sporting. Confidence is an important quality single women are always attracted to. Still uncertain about what to wear on your video dates or in real life? Keep reading!

Here are virtual date styling tips for single men;

Neutral Colour Scheme


Start with neutral coloured garments. Find neutral tones like black, white, brown, dark green, beige, or grey. These colours work for all seasons and suit every male. No matter what your skin tone or body shape is, a classic white button-up shirt or a grey cotton fleece sweater will make you look date ready. When shopping or finding neutrals, pick a neutral colour palette that you like and stick to it. 

Brighten It Up

Best Toronto Matchmaker
Virtual Date Style Tips For Men @chinedustyle

Add a pop of colour to your neutral look. Realtor and philanthropist Mitch Krystantos is sporting a custom red jacket by C|E Clothiers. Colours can be a visual stimulator and can give off a message without you saying a single word. Colours can influence your mood and your date’s mood too. If the colours aren’t your thing, don’t worry. Start small. You can add subtle pops of colour in your wardrobe. Throw on your colourful tie, watch, t-shirt, or socks. For video dating, pay attention to what you’re wearing waist up. If you are not afraid of bright colours, then definitely make yourself stand out by wearing that bright yellow sweatshirt or baby blue blazer.

Timeless Classics

best toronto matchmaker
Virtual-Styling-Tips-For-Men @kamanastyles

Start with the foundations of style. Classic pieces will always be fashionable and have always helped men bring out their Alpha. As a professional matchmaker, women share with me; they appreciate masculine qualities, especially when it comes to attire. A collection of classic garments has so much versatility because you can make so many different combinations out of it to create a variety of looks. Don’t be afraid to dress up during your virtual date. Just because you’re at home, doesn’t mean you can throw on your tailored suit! 

Bold & Loud

Best Millionaire Matchmaker
Virtual Style Tips For Men @the_coopink

Prints and patterns can be bold and loud or neutral and classic. Don’t be afraid to go bold and loud. If a patterned button-up shirt or colourful socks are your thing, wear them! Pair it with a neutral jean or black pants. Balancing the boldness can help complement the look. Remember, you want your date to remember how you look first and not questioning what you’re wearing the entire night.

Accessories Matter


Accessories can pull the whole look together. Look in front of a mirror and try on one piece of accessory with your overall look. If a small accessory sticks, that’s the one you choose. When choosing which fashion accessory to wear, consider how it accents your entire ensemble. Build on top and if you think you’re wearing too much, remove each piece one at a time until you find the perfect combination. You’ll be flattering your date on how well put together you look for your virtual date!

The best virtual dating look you can wear is Confidence! To be confident is to wear the right clothing. The style, cut, fit, colour all matters, but how it makes you feel is essential. If something you throw on doesn’t give you that “I look good” vibe, put it aside. Keep filtering through different combinations of the pieces in your closet, and you’ll come across a look you genuinely feel great wearing. Take a full-body photo of yourself in front of a mirror so that you can reference it for future dates. Once you find the look, wear it on your next virtual date. Channel your Alpha male vibes through your wardrobe, and you’ll be meeting your potential new partner in no time!

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.

Share It

Related Posts

Leave a Comment

Your email address will not be published. Required fields are marked *