Casual Styling Tips for a Virtual Date for Men

I find that one of the biggest pain points for my clients after they book their photoshoot is figuring out what to wear. That’s why I brought on an expert personal stylist, Kim Steele, to my team to help my online dating clients select the exact outfits to wear at their photoshoot that will flatter them, photograph well, and accurately reflect their own style or a style they’d like to embrace.

Unfortunately, the stress of figuring out what to wear isn’t unique to photoshoots. With so many first dates taking place online these days due to COVID-19, I asked Kim to share some of her best styling tips on how to look your best on a Zoom date.

---

So, you’re a guy getting ready for a casual virtual date—now, what should you wear? It’s important to keep in mind that YOU should be the focal point, not your clothing. In this post, I am going to walk you through how to make styling choices that will make you feel and look confident but also won’t upstage you in the process. 

Let's start with casual clothing staples that every guy should have in their closet:

1. A great fitting pair of mid to dark-wash jeans. I find slim fit or straight leg to be the most flattering.

2. A selection of at least three solid-colored crew-neck t-shirts in black, grey, and white (t-shirts are amazing layering pieces and a cornerstone to many great looks).

3. A casual button-down shirt (a minimum of one, but two or three are even better). This can be a simple plaid, solid-colored, or another subtle pattern. Long sleeves in a cotton fabric work best and give you a lot of bang as you can wear them almost all year round.

4. A solid-colored, long-sleeved Henley shirt (again, at least one, if not two or three). Just like with the casual button-down, you’ll get lots of use out of these as you can wear them alone or layered with a zip-front hoodie or even a flannel shirt.

5. A great casual shoe. Okay, yes, chances are your virtual date will not see them, but with the great first impression you’re going to make, they’ll eventually want to meet and you’ll have your look nailed down from head to toe! 

6. A casual slip-on boot works with all the other clothing items mentioned above and makes for a great finishing touch.

Here is a look inspired from the list above with links to purchase: dark washed jeans with a grey t-shirt underneath a long-sleeved grey and white plaid shirt worn with black Chukka boots.

This is an easygoing look that will represent well on your virtual date as well in-person. With the basics suggested above, you can mix and match to create all kinds of combinations. With the basics suggested above, you can mix and match to create all kinds of combinations. This is only the tip of the iceberg of discovering how to best represent yourself to the world!

Hair and Grooming

So we’ve addressed the clothing basics. Let’s talk about hair and grooming. If you are sitting in front of a computer screen for this date, your face and hair are really front and center. This is the place to put in a little extra time and effort!  

Have you thought about changing up your look? Talk about a great time to road test a new haircut or facial hair! Right now, a popular style for men’s hair is a cut tight on the sides and back with some extra length on top and then styled with product to pull the look together. I know some of you might have chosen to sport longer hair along with a beard and mustache in the pandemic, but maybe for the new year, it's out with the old and in with the new! After all, it’s hair we are talking here and it will grow back if you don’t end up loving your new look. It’s a good idea to see your barber or hairdresser every four to six weeks, depending on the look you aspire to. It's also an opportunity to shape up your brows as well! Yes, really. There are many ways to go about this such as waxing, threading, or tweezing, and some hair professionals are willing to trim brows as well.

Using a bit of product at the start of your day can make all the difference in the world. Do you really need to use hair product? Yes, you do. It gives you a more polished look and also conveys to your date that you put in that extra effort to look your best for your date. Since this is a more casual date you're getting ready for, I’m going to keep it simple with a suggestion for a product that will make your hair look (and smell!) amazing.

Skincare

Now let's discuss skincare, which is not just for the ladies. I am not suggesting you need to fill your medicine cabinet with products for your face, but you do need to have a regimen that cleans your face and protects your skin so that you will continue to look fantastic for years to come. I recommend a facial wash and moisturizer with SPF as an easy fix for your daily needs.

final thoughts

Even if some of these suggestions fall outside of your comfort zone, I encourage you to go ahead and give them a try. I am here to make you look great because if you don’t look great it puts me out of business! I love what I do and take great pride in helping others discover a side of themselves they can’t see.

Here’s to an amazing casual virtual first date! Look out for my next post about how to step up your attire for a formal virtual date. Remember to trust the process and have some fun with this—you’re in for an amazing adventure!