5 items to wear on a date if you want to impress her

As a guy, dates are tough. On one hand, you want to look good to impress her. On the other hand, you want to seem casual, like getting dates for you is no big deal…

What you wear is a big part of how she perceives you. Although we’re told not to judge books by their covers, we often do, especially on first dates. In essence, first dates are “tryouts” for relationships – you better be giving it your all in terms of appearance.

Here are five items to wear on dates that you cannot go wrong with. Add these items to your current wardrobe and watch as the smiles you get on your romantic dates get bigger and bigger.

1 – A simple leather watch

Watches can put the finishing touch on your outfit – or, it can completely ruin the vibe that you’re trying to cultivate.

The big, shiny, tacky silver watches are overplayed. We’re not saying that you can’t look good in one – but it’s much easier to look good in a simpler watch.

Get a watch with a clean face (no jewels or other loud elements) and a solid leather strap.

The strap can be brown, black, or really any other color – just make sure that everything fits well with the rest of your outfit. You want your watch to pull everything together, not draw attention away from you.

Michael Kors Hawthorne Silver-tone Leather Watch

Michael Kors Hawthorne Silver-tone Leather Watch

#2 – Dress shoes or simple sneakers

Wearing dress shoes on a walk around the park looks weird. Wearing sneakers to an upscale bar looks childish – and they might not even allow you in.

Determine how formal your date location is. If it’s formal, go for some solid-colored oxford dress shoes. Your shoes should always match your belt – black on black or brown on brown.

If it’s a more casual date, go with sneakers – but not just any sneakers. Make sure that they’re unique (no New Balance running shoes, please) and clean.

Ask any girl and they’ll say that after the face, the shoes are usually where their eyes dart first.

Loafers vs Oxfords? Loafers vs Oxfords?

Loafers vs Oxfords? Both models available at Urban Sapes.

#3 – An appropriate dress shirt

Your shirt should match the vibe of the date you’re going for.

If it’s formal, a plain-black dress shirt can do wonders for you. On the other hand, if you’re going for a walk around the park, a plain-black dress shirt will stick out like a sore thumb.

As a general rule of thumb, if it’s formal, stick with simplicity. If it’s casual, feel free to spice it up – bright colors, patterns, etc.

We’d always recommend sticking to button ups – save the t-shirts for the active dates, like hiking or rock climbing.

As always, make sure that your shirt actually fits you, or you’ll look bad no matter what you wear.

Dress shirt for MenUrban Sapes dress shirt for $27.99.

#4 – Pants that fit

Have you ever seen someone walking around in a suit that’s two sizes too big for him or her? If you wear pants that are too big, you’ll look even worse than that person.

Get pants that fit well. Too baggy and you’ll look like a slob. Too tight and your date might be turned off.

It’s a difficult medium to reach. Try out different brands until you find the right fit, or take your favorite pants and head to a tailor to get them fitting perfectly.

Dress pants with dress shoes is always a winning bet, but feel free to mix in high-quality jeans if you have them to create a more casual look.


#5 – A blazer or suitable jacket

You’re going to be wearing your jacket when you first see your date – so really, it’s one of the most important parts of your outfit.

Get a suit blazer if you’re going formal. Suit blazers take button up shirts and dress them up.

Get a regular jacket – bomber jacket, windbreaker, etc. – if it’s more casual. Remember, you don’t always want to look completely formal on dates. Showing her that you have style outside of dress clothes can earn you major points… right away.


Sky blue blazer & classic black blazer available here from $54.99

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