How Should You Dress On A First Date?
Answer: it depends.
It depends on the venue, the weather/season, your age, your personal aesthetic etc.
Regardless, here’s my general framework to help you make the right first impression no matter who you are…
Answer: it depends.
It depends on the venue, the weather/season, your age, your personal aesthetic etc.
Regardless, here’s my general framework to help you make the right first impression no matter who you are…
My first date style philosophy is about expressing the following three qualities with your look or aesthetic:
✔️Maturity
✔️Formality
✔️Class
Let’s discuss how you can do this...
✔️Maturity
✔️Formality
✔️Class
Let’s discuss how you can do this...
Maturity
It doesn’t matter if you’re 22 years old or 42 years old, MATURITY is a key quality you want to express with your style. You want your date to know she is out with a MAN and not a BOY.
How does this translate for your style?
It doesn’t matter if you’re 22 years old or 42 years old, MATURITY is a key quality you want to express with your style. You want your date to know she is out with a MAN and not a BOY.
How does this translate for your style?
It means skip the hoodies, the ball caps, the sneakers, and the lighter wash jeans. Especially within the context of an EVENING date at a nicer bar or restaurant.
Instead, think of nicer knitwear in merino wool or cashmere, proper dress slacks or chinos (or potentially dark denim jeans), legit footwear like loafers, nicer boots, or leather lace ups etc.
Formality
If you’re out on a date in the evening your best bet is to stick to a DARKER color palette. Darker are considered more FORMAL looking. This doesn’t mean you can’t add a bit of color…just be sure to incorporate it within an overall darker palette.
If you’re out on a date in the evening your best bet is to stick to a DARKER color palette. Darker are considered more FORMAL looking. This doesn’t mean you can’t add a bit of color…just be sure to incorporate it within an overall darker palette.
And while I don’t think you need to wear a suit, I suggest incorporating more FORMAL looking items into your date night fits be it a collared shirt, odd jacket/blazer, dress slacks, dress shoes etc.
One of the best plays you can make here is taking traditionally formal looking items and dressing them down a bit to soften the look.
E.g. taking a black or charcoal grey suit and pairing it with a plain t-shirt:
E.g. taking a black or charcoal grey suit and pairing it with a plain t-shirt:
Or wearing a collared shirt but leaving out the tie:
Class
Finally, you want to exude nothing but pure CLASS with your aesthetic. Focusing on those first two qualities (maturity and formality) will go a long way to help but small details like the right accessories and attention to detail will take you over the top.
Finally, you want to exude nothing but pure CLASS with your aesthetic. Focusing on those first two qualities (maturity and formality) will go a long way to help but small details like the right accessories and attention to detail will take you over the top.
What kinds of accessories and details?
✔️Wearing a LEGIT watch instead of a smart watch
✔️A proper leather card wallet or money clip vs some overstuffed monstrosity
✔️A signature fragrance that works with your body’s chemistry
✔️Well groomed hair/beard and good hygiene
✔️Wearing a LEGIT watch instead of a smart watch
✔️A proper leather card wallet or money clip vs some overstuffed monstrosity
✔️A signature fragrance that works with your body’s chemistry
✔️Well groomed hair/beard and good hygiene
If you don’t think women pay attention to minor details like this, you are WRONG. These are the sorts of things that put your look over the top.
Again, these are just some GENERAL principles. There is a ton of context and nuance at play here but hopefully this can help guide you in making the BEST first impression.
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