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10 Style Mistakes To Avoid on a Date

10 Style Mistakes To Avoid on a Date


If the first date is when you show the best version of yourself, then the following dates are when you begin to peel back the layers. You find more of a routine with each other and with that, a level of comfort.  

A heightened sense of comfort shouldn’t lead to a diminished sense of effort on future dates. Making an effort in your appearance will show the guy you're dating that you care and communicate your sense of style. 

Whether it’s your 5th date or your 5th month of dating, here are 10 style mistakes to avoid on a date. 

This isn’t a piece designed to pick your outfit for you. It won’t dictate what type of shirt is popular or if you can wear white socks with black shoes. That’s fashion and entirely different. As Tan France explains,

“Fashion is the dominant style within a given culture at a certain time. It refers to popular ways of dressing during a specific era.”

Style is personal because it’s your self-expression to the world. It’s a composite of everything from the clothes you wear to the haircut you choose. Unlike fashion, which is a collective opinion of popular clothing, style is an individualistic aesthetic created by your experiences. 

As you share experiences with the guy you’re dating, consider how to showcase your evolving style.  

Mask for Masc

Wearing a mask on a date

Dating amid a pandemic is how we live now, so invest in a cloth mask. With consistently evolving regulations and varied requests from businesses, it’s smart to always have a cloth face mask handy when you’re on a date.

You don’t want to miss a dinner reservation or not be admitted somewhere because you forgot a mask. Coming to the date prepared demonstrates your responsibility to health and respect for the guy you’re meeting.   

Unpressed Doesn't Impress

Unpressed clothes isn't suitable for a date

Give yourself time to put on fresh clothes before you leave for a date. Never show up wearing wrinkled clothes that look like they were balled in a drawer or like you just woke from a 3-hour nap. 

Allow yourself the extra minutes to iron your clothes or run them in the dryer to remove pesky wrinkles. It demonstrates the effort you made regardless of how casual your hang is. 

‘Tis the Season

Dress appropriately for the season, specifically the weather. Nobody wants to date the guy wearing shorts when it’s 40 degrees outside. Worse, you don’t want to cut your date short because you’re sweating through your clothes. 

Wearing temperature appropriate clothing will keep you comfortable and cool. If you’re unsure about what to expect, bring a layering piece like a cardigan, denim jacket, or bomber that can easily be removed. 

Don’t Go Deep

Deep V T-shirt style

T-shirts are a versatile staple of men's fashion. They go with (almost) everything; there are countless colors and styles to choose from. V-necks are an excellent T-shirt style but don’t rock a deep V. 

The point of the V should be about 3” from your collarbone when you wear the T-shirt. If you have man-cleavage while wearing your V-neck, then your V is too deep. It’s a dated style that’s best left in 2009. 


Deciding to tuck in your shirt is a personal choice of style and comfort except in the case of button down shirts. They have design elements specifically for tucking, or not. Here is your definitive guide to knowing if a button down is designed to be tucked in. 


Men wearing sun glasses

Sunglasses are an infinitely cool fashion accessory. They’re the perfect combination of function and style.  If a fashion accessory is supposed to complete a look, you can never go wrong wearing sunglasses unless you're indoors. Once you’ve entered an interior space, take your sunglasses off. 

Beware the Square

If fanny packs can make a fashion comeback than any trend can. Except for square-toed shoes. 

Oxfords, loafers, and boots with a blunt square toe look disproportionate, particularly when worn with skinny denim or slim chinos. The shoe’s trademark horizontal toe line and wide proportions are visually awkward. 

Shoes shapes

Clean Sole

There are few fashion rules when it comes to shoes. Sneakers can be worn with suiting. Athletic shoes became streetwear. Shoes don’t have to match your belt and can be adorned with metal studs, chains, or grommets. 

Whatever style you wear, clean your shoes before you leave for the date. Shoes say a lot about the person wearing them. Make sure that your laces, shoes, and soles are saying the right things about you. 


Grooming before the date

Grooming is part of being a man. Ensure that your eyebrows are separated. Keep your stubble at a good length. Condition your beard and keep it free of errant hairs. Trim body hair where it’s unruly. 

While it’s important to tidy up before a date, don’t over-groom yourself. It’s a quick slide into preening territory and that’s not a good look on any guy. 

Fashion Checklist

It’s great to showcase your fashion acumen, but there’s a danger in wearing all the loudest trends at once. Show your fashion aptitude in a thoughtful and edited way to avoid looking like you shopped a trend checklist before the date. 

Men outfit

Style is incorporating fashion into your holistic sense of self. Don’t let fashion be the only thing that your date sees.

Tim Gunn has a saying that "style is about the way you hold yourself and move through the world." As you prepare for your next date, ask yourself, "How are you moving?"


Matt McFall for KeYou