Dear NJ First Dates: I just signed up for my first speed dating night in Hoboken and I am currently staring into my closet in a mild panic. What on earth do I wear? — Overthinking in Jersey City
Dear Overthinking,
First, take a breath — the panic is normal, and it evaporates about ninety seconds after the first bell rings. Second, you’ve already done the hard part by signing up. Now let’s solve the closet.
Here’s the thing about speed dating: each conversation lasts only a few minutes. That’s long enough for someone to remember how you made them feel, and exactly short enough that your outfit is doing real work in the background. You want it helping, not distracting — you, on a very good day.
The only rule that really matters
Dress like the best version of a normal night out. That’s it. Smart casual is the sweet spot at nearly every event we run: polished enough to show you made an effort, relaxed enough that you still feel like yourself. If an outfit would work for drinks with friends at a nice Hoboken bar — which is literally where you’ll be — it works for speed dating.
For the ladies
A top you love with dark jeans, a casual dress, or a skirt with a sweater — all perfect. One piece with a little personality (a color you wear well, an interesting earring, a great jacket) gives your dates an easy opening line, and you’d be surprised how many conversations start with a compliment. Skip anything you’d tug at, adjust, or second-guess mid-conversation. If you plan to wear heels, remember you’ll be on them getting there — Hoboken sidewalks have character, and character is hard on stilettos.
For the gentlemen
A collared shirt or a clean, well-fitting crew neck, dark jeans or chinos, and real shoes — that combination has never once failed a man at one of our events. A blazer over it is a bonus, not a requirement. The two details people actually notice: fit and freshness. A shirt that fits beats an expensive one that doesn’t, and wrinkles read as “rolled straight off the couch.” Go easy on the cologne; you’ll be sitting close, and less is genuinely more.
Dress for the room, not the runway
Some practical notes from people who host these nights every week: you’ll be sitting close to your dates, usually at a bar or lounge table, and one of you rotates seats every few minutes. So — comfortable shoes, layers you can shed if the room runs warm, and nothing so precious you’ll worry about a bumped drink. In winter, bring a coat you don’t mind draping over a chair; not every venue has a coat check.
Leave these at home
Gym clothes and the interview suit — one says you didn’t try, the other says you’re about to ask where we see ourselves in five years. If you’re coming straight from the office, just lose the tie and undo a button. Also on the bench: brand-new shoes you haven’t broken in, loud logos that do the talking for you, and anything — however fabulous — that isn’t comfortable to sit in for two hours.
The confidence clause
Our best advice fits in one sentence: wear the thing you’ve already been complimented in. Not the outfit you bought for the person you think you should be — the one where you catch the mirror and think, “yeah, alright.” Confidence is the single most attractive thing anyone brings to a speed dating table, and the right outfit is simply the one that lets yours show up.
You’re going to do great. And when you find yourself deep in a conversation that makes the bell feel like it rang too soon — that’s the whole point, and no one will remember what anyone was wearing.
Ready to put the outfit to work? Browse our upcoming speed dating events and grab a spot.
— The NJ First Dates Team