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What to wear on a first date (for guys)
You've got a date. You've also got a closet full of stuff and no idea which of it works. Let's keep this simple. Pick the outfit by the place, make sure it fits, and get a haircut. That covers most of it.
The rule
Dress one small step above the place. Fit matters more than anything you buy. And wear something you've worn before, so you know it's comfortable and you're not fussing with it all night.
Drinks at a casual bar
Dark jeans that fit, a solid tee in a good fabric or a henley, and an overshirt or light jacket. Clean white sneakers or casual boots. This is the outfit that works almost everywhere.
Coffee or a daytime date
Chinos or dark jeans, a polo or a clean crewneck sweater, simple sneakers. Relaxed but put together. Think "I have my life together on a Saturday."
A nicer dinner
Dark jeans or chinos, a button up shirt, sleeves rolled if it's casual. Add an unstructured blazer or a nice jacket if the place is upscale. Leather shoes or clean minimal sneakers. No tie needed unless the restaurant says so.
Something active
Mini golf, a walk, a market, bowling. Jeans or chinos you can move in, a tee or polo, a light layer. Comfortable shoes that still look clean. Not gym clothes. Active, not athletic.
Grooming, the cheap upgrade
Haircut a few days before. Beard trimmed or a clean shave. Nails short and clean. A little cologne, one or two sprays. Fresh breath. All of this is noticed more than the shirt brand.
What to skip
Graphic tees, anything wrinkled or faded, baggy clothes, beat up shoes, a heavy cloud of cologne, and anything brand new you haven't tested yet.
Texts you can send
is this place more jeans or more button up
ok what am i wearing to this. need to know if i should iron
thanks. my roommate approved it so you can thank him too
A woman's read
Here's what goes through her head when you walk in, honestly. Does he look clean? Does it fit? Does he look comfortable? That's mostly it. She's not grading your outfit. She's picking up whether you put in a little effort and whether you're relaxed. A guy in a fitted tee and a fresh haircut beats a guy in an expensive shirt that's two sizes too big every time.
The move
The day before, try the full outfit on and sit down in it. If anything is baggy, wrinkled or uncomfortable, swap that one piece. Book a haircut for two or three days before.
If you're not sure about the place
Look it up. Check photos of the inside, or just ask her. It's not weird. If you want the bigger picture on building a small date wardrobe, read how to dress better for dates. Still picking the spot? Val has first date ideas that aren't boring, and conversation topics for once you're there.
Questions guys ask
What should a guy wear on a first date?
Dark jeans that fit, a solid tee or casual button up, an overshirt or jacket, and clean simple shoes. Adjust one step up or down for the place.
Should I dress up for a first date?
One small step above the place is the sweet spot. You want to look like you tried, not like you are going to a wedding.
Are sneakers okay for a first date?
Yes, if they are clean and simple. Plain white or leather sneakers work for most first dates.
What colors should a guy wear on a first date?
Simple ones that suit you. Navy, white, black, gray and olive are easy and hard to get wrong.
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