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What not to wear … on a first date

Written by Christine Morrison, Wednesday, August 31st, 2016 in Fashion, The Style Guide

image -- what not to wear ... on a first dateWomen aren’t that high maintenance – at least the keepers aren’t – but we do have higher standards when you escort us out for first dates.  Sure, you can’t judge a book by its cover, but you can judge a man by what he wears in these circumstances.  Take note, gentlemen.

Never wear scuffed shoes

How bad is a slightly beat up shoe, and what does it say about you?  It says you’re not into the details.  What’s next…not knowing our last name by the end of the night?  Put your best foot forward.  Invest in a shoeshine.  They’re cheap, so you don’t look like you are.

Conversely, a little scruff on the face…well, that’s just downright sexy.

Wear clothing that fits

Why wear a billowy shirt or baggy pants that disguise your hard work at the gym — or attempt to camouflage that you would rather watch sports over a few beers vs. participate in them.  First dates may not be the time to showcase all your flaws (ahem, a video game obsession is best brought to the table at least after the first kiss), but your appearance should be your A-game.  Regardless of your body’s imperfections, shirts and pants that are tailored or fit you properly off the rack, are way more flattering and can help you appear effortlessly cool.

Minimize the labels

You may pride yourself on being a style guy, but women don’t want to be overshadowed from the start.  It’s the same reason female wedding attendees never wear white.  Eliminate the Burberry checked shirt paired with Hermes logo belt and topped with Gucci loafers.  Instead, let your own personality and charm shine through with classic cuts and neutral pieces in “want to be touched” fabrics such as cashmere or cotton with a super high thread count.

This doesn’t mean you don’t get to impress a new girl with your sartorial prowess.  Feel free to chat about your love of sneakers – and what guy isn’t a sneaker head these days?  For instance, Raf Simons’ new take on Stan Smiths could be a great conversation starter during that first drink when nerves are high.


Like the amount of alcohol consumed on a first date, with fragrance less is more.  No one wants to smell you well before you arrive … especially a new prospect.

With that said, there is nothing wrong with scent tucked into your aftershave, moisturizer, or both, since layering the aroma will make it subtly last longer.  If you are dousing yourself with musky fluids, or God forbid deodorant body sprays, to cover up poor hygiene, well then you should not be on the date in the first place.  Running off for your first get together after a pickup game of basketball is rude.  Take a shower dude.

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