Fall Getup Week: What to Wear on (Almost) Any First Date

Fall Getup Week: What to Wear on (Almost) Any First Date
The fail-safe outfit you can wear on a date when you're not sure how dressed up to be.

What are you supposed to wear on a first date?

This is a question I’ve been pondering for a long time, because dressing for first dates is super challenging. You don’t want to wear a sport coat if your date is going to show up in street casual. And you won’t want to rock a t-shirt and jeans if they're dressed up. It’s a balancing act – and because it’s a first date the stakes can feel really high.

You need the Goldilocks of outfits: not too dressy, not too casual. And definitely not generic, but not fashion-y either.

Then there’s the problem of seasons. We’re in early fall, and in warmer places it’s still too hot for a jacket, whether it’s denim or a blazer.

That’s why I’m excited to share my own personal first date Getup. I've worn this on a few and it's proven to work in different types of places on different types of dates.

what to wear on a first date   men's outfit ideas Fall Getup Week infographic

Everlane chambray shirt denim jacket j.crew shawl collar leather jacket uniqlo sportcoat amazon belt levis 512 mvmt watch mont blanc cologne listerine strips rogue industries olive suede boots thursday

Is This The Perfect First Date Getup?

What I like most about this outfit is that says something very clearly and simply: This look is intentional.

There aren’t a lot of pieces: a shirt, jeans, boots, and a watch. There aren’t a lot of colors: gray, charcoal, and olive. But the overall effect is one of, “that guy’s dressed really well,” and I draw a lot of confidence from that.

For style scholars, I suppose this look qualifies as minimalist, and definitely casual. The textured gray shirt from Frank & Oak (currently sold out but similar options are available from Everlane and J.Crew) is paired with darker gray charcoal jeans from Levi's, playing on monochromatic shades.

textured gray mens shirt

The boots are my current go-to from Thursday Boots: the Captain in dark olive suede. Tonally, they strike this great balance between black and brown, but aren’t either. The olive suede is unique without being flashy and add a layer of intentionality that makes this Getup pop.

The watch is a one-tone MVMT chronograph-style timepiece with NATO strap. It adds another layer to the minimalist, intentional – there’s that word again! – vibe.

But enough about form… what about this Getup’s function?

first date outfit

What Kind Of First Date Does This Work For?

This Getup works basically anywhere you’d want to go on a first date. I’ve worn it to a fancy, menu-less cocktail bar and felt perfectly at home. I’ve also worn it to a less-traditional first date at a 80's arcade and also felt totally appropriate. Day time coffee date? Check. Star-gazing at the observatory? Check.

Are there other, more casual options for coffee? Sure. But you could wear this and feel at home.

This brings me to the last thing I’m proud of with this Getup: it removes some of the mental energy of prepping for a first date. You’re already excited. You’re already doing the messaging dance of trying to figure out a place to go that’s not to far from them and not too far from you, and so on.

If you’re looking for that not-too-dressy-not-too-casual first date outfit, give this one a try. My only concern? If you live in the LA area, I hope we don’t run into each other wearing the same thing on a night out!

Andrew Snavely

Andrew founded Primer in 2008 and brings 15+ years of men's style expertise. Known for his practical, relatable approach to style and self-development, he has been a recognized speaker at conferences and has styled work for top brands. Off-duty, he loves photography & editing, and enjoys road trips with his dog, Leela. Raised in rural Pennsylvania, educated in DC, and living in LA for nearly 20 years, Andrew's diverse experiences shape the relatable and real-world advice that has helped millions through Primer. On Instagram: @andrewsnavely and @primermagazine.