What to Wear For Your First Date Night

As seen in the Baltimore Business Journal
By Judah Estreicher – Contributor, Baltimore Business Journal
Jan 23, 2020
Happy New Year, fellas! I know we are all just recovering from the holiday season, but with the start of a new decade, it’s essential that we keep working on our style status. We can start by exploring appropriate attire for a few common occasions you might find yourself experiencing. First up: what to wear for date night.

No matter the date scenario, there are a few principles you would do well to adhere to. First of all, make sure your clothes fit well; you won’t impress your date with baggy clothes or a pair of pants that last fit you well in high school. Also, be sure that you smell good. If you are headed to your date feeling less than fresh, a change of clothes might be a good idea. And, spritzing yourself with a bit of cologne always ups your game (though let’s not overdo it).

Finally, don’t choose an outfit that is too daring. Your date shouldn’t feel like it’s the Met Gala, so stick to what you know and wear it well.

As for the type of date:

The first date

For your first date, you definitely want to make an impression, and not the wrong one. Dressing nice will definitely impress. I would suggest a tailored pair of slacks (no jeans), button-up shirt and a statement jacket. The slacks and shirt keep the look grounded and polished, and the jacket is your chance to show your style. Try a bomber or a leather jacket for something classic and edgy, or go for a nice overcoat on colder nights. Steer clear of sneakers and ties — sneakers are a bit too casual and ties can feel stuffy or intimidating.

The dinner date

Your attire for this occasion depends on where you’re going to dinner. You will earn some points with your date if you choose the place. For attire, let’s again shy away from the jeans (even if others might be wearing them) and go with a nice pair of slacks. If you are headed to a higher-end joint, go for a matching suit jacket and a button-up shirt. If it’s somewhere a bit more casual, try pairing a sweater with your shirt.

The movie date

We all encounter a classic date to the movies at some point. It can be tempting to go quite casual when you know you will be sitting in the dark for two hours, but make sure you still show up looking put-together. I would recommend dark wash jeans and a button-up shirt topped with a blazer. You will look casual, but put-together and have the layers to keep you warm in a drafty theater (or to offer to your shivering date — chivalry points).

The stay-in date

There comes a time when you feel comfortable inviting your date over to your place or vice-versa. This will undoubtedly be a more casual occasion, but unless you are a married couple, this is not an occasion for sweats. Instead, go with jeans or chinos and a sweater, or a plain t-shirt and jacket for warmer weather. I would also recommend that you don’t wear socks with holes in them, as that could be a bit off-putting for your date.

There you have it: a guide to dressing to impress for a myriad of dates. If you have a scenario you’re unsure of how to dress for, just send an email at [email protected] at to ask me about it.


Leave a Reply

Your email address will not be published. Required fields are marked *

Jbd Logo-JBD Clothiers