It is so easy for guys to be dressed up, yet they do not do it! 

One main rule: Keep it simple. When in doubt, keep it simple. 

Men do not have to pick out a ball gown. If you are unsure, keep it simple.

Wear white, black, or navy. You are good. Avoid grey. It is boring and I hate it. It is unapproachable. If Brad Pitt was wearing grey, I still would think, “Really?” But then again, you are probably not Brad Pitt. 

Do not wear jeans. 

Wear something smarter. If you know she is coming in a beautiful dress, make her feel like you are worth how much time she she put into her look, planning nail, hair, and skin appointments for this. 

Waxing everything painfully, botox and filler injections, expensive perfume, time in the shower shaving certain spots, spending a fortune on lasering her body, the pilates class she scheduled before this, how expensive each piece of makeup is – it is $90 for my eyeshadow, and $45 for my lipstick, her expensive purse, her gorgeous shoes, etc. 

Her skincare routine probably cost more than how much you spend on groceries in two weeks. I know this, because mine does, and I do not even have that much of high end stuff. Especially if she is a high caliber woman who plans to keep it tight til she is 80. So do not wear jeans. Wear smart trousers. 

Never wear a tshirt. A tshirt is underwear. I hate when grown men wear tshirts. You look like a child. It tells me you do not know how to dress appropriately for your age. A t-shirt is underwear. 

Quick story time: 

I was out with a platonic friend. I was in a beautiful dress that was modest where my shoulders were covered, no cleavage was showing. It was not short at all. I naturally have long slim legs. I was wearing 2.5 inch wedge sandals with it, because it was hot and it was day time. The wedges were not tall at all, but I know how to dress and they make my legs look longer. No matter what I do, my legs are long for my petite height. 

This guy said, “I don’t think we can go to this place, because you are scantily clad.” I sent him to his funeral with a closed casket, because I shredded him to pieces. I told him, “You are wearing a tshirt, basketball shorts, and flip flops. You are telling me I am under dressed, when you are the one wearing a tshirt. That is underwear on the outside.” 

He shut his mouth instantly. Flip flops are for the beach. Basketball shorts are for basketball. Tshirts are underwear. 

Wear a smart jacket. 

You can also opt for beautiful wool, cotton, or cashmere sweater. I personally love cashmere and silk blends. I purchased a couple silk and cashmere blend cardigans on sale at J. Crew for $37. For smart jackets, I like personally like Ralph Lauren Purple Label, J. Crew, if you have the budget for it- Zegna or Armani, or any Savile Row suit maker. For older gentlemen, Brunello Cuccinelli. 

No lumberjack shirts aka plaid button ups. Only solids, stripes, very small polka dots, or tatterwall. If you are Scottish, your family’s tartan. Sharing your heritage is exceptionally attractive.

Dress a little bit smarter than regular.

Shoes, belts, and watch make your outfit. 

• Shoes need to be clean, no scuffs. The rule is the sleeker the more formal. More embellishments like laces and brogue layers make them more casual. If you have a sleek loafer with velvet or patent leather, it is more formal. I would stick to a casual dress shoe if it is a first date, or if it is a casual date, would even go for a chukka. 

• If you are not wearing a jacket, wear a french cut shirt or double cuff. I personally am obsessed and have started my own cufflinks collection I am obsessed with. For cufflinks, generally avoid yellow gold. Go for rose gold or silver instead. Silver is always timeless just as a heads up. If you propose to a woman, give her a silver or white gold ring. If the date is more casual, single cuff shirts are fine. I also love all the dfiferent cuff shapes. Rounded and sharp squared French cuff, either way are my two top favourites. 

• Belt just needs to be simple. Make sure the holes are not worn. Get a good leather belt for less than $50 anywhere. But make sure you take care of it. Be nice to it. 

• Watches do not have to be opulent or large like flashy jewelry. I think it is tacky if a watch is too big. If I can see the numbers across the room, your watch is too big. Wear that as your at home watch. I love a simple leather band. Do not have a casio. You are not from the 80s. The 80s were terrible. To me Casio says, “I do not have a steady job. One day when I do, I will throw this watch away.” Avoid Casio altogether. 

Elegance is in the details. When in doubt, keep it simple. 

Find more etiquette posts here. Interested in a lesson? Book a course with the links below and become the most polished version of you.