Hey man. Thanks for writing in. This is a great question and something I have a fairly strong point of view about. For many years, our Atlanta shop was right next door to a pretty popular bar, and right around the time that we would start closing down for the evening was when things were starting to get going over there. People would pass our shop on the way over and I’d see all these women done up to the nines in sundresses and heels and their hair done… and they’d be walking in with guys in t-shirts and cargo shorts and, like, Reef flip-flops. And it bummed me out. Not because there’s anything wrong with casual clothes, necessarily, it’s just that they were so mismatched with their dates, who had put in all this effort. It made me want to pull them aside and get them in a pair of jeans or a proper shirt and them send them back over. I needed one of those vaudeville shepherd’s crooks. Anyway. We say this a lot, but so much of dressing is about manners, and when it comes to a date – or any social engagement, I suppose – your levels of effort should feel roughly commensurate to those around you. But this gets a lot harder on a date when you may not know who you’re meeting very well… let alone what they’re going to show up wearing. So I understand your conundrum here. First (and second) (and third) impressions are important, and you can’t be showing up as Spicoli or T Howell III.
So I’m going to give you a safe-bet formula for striking the right balance between relaxed and done up: POLO + 5-POCKETS + CASUAL SPORT COAT. (Also, for the record, I may be married but I’m still in the dating game… just with the same woman. This is all AM-approved.) For me, this combination has always had kind of casual elegance to it… very California, in a funny way. There’s a great image of Harrison Ford in a navy polo and a navy sport coat and blue jeans that was probably taken 40+ years ago – which goes to show you how timeless this look is. Most importantly, it splits the difference: if your date is really dressed up, great, you’ve got a jacket on. If she’s dressed more casually, that’s fine, you’re in a polo shirt and jeans and you don’t have a tie on. You can even get rid of the jacket entirely and sling it over your arm. Whether you’re showing up at the nicest place or the diviest place, it’s going to look great at both of them.
Let’s start at the top. While I usually try to keep my advice pretty brand-agnostic… the polo in this equation is ours specifically. I’m talking about a Sid Mashburn polo. A performance polo from the pro shop is not going to do what you need it to here. You don’t want the cling and the collar’s not right for wearing with a jacket. Our polo is made with a cut-and-sew collar that’s designed to stand up under a sport coat. It’s meant to have a tinge more formality to it than your average polo, but it’s still soft and easygoing, with a slight roll that makes sense with the jacket lapels. So the collar on ours is key, but the fabric is important too: it’s pima pique, which is the one of the highest qualities of cotton that you can get, made with fibers that are extra long and almost silky. This gives you a knit that is both super soft and super strong, with minimal pilling. Color-wise, I’m going to recommend a softer and/or more neutral color – white, pale blue or pink, navy – and save the pop color for daytime. Or, hey, a later date.
Next up – a pair of 5-pockets. Blue jeans, white cords, garment-dyed canvas, whatever. It’s hard to mess this up. That said, just like with the polo, I may not come on too strong with too bright of a color. You want the focus to be on you, not on your green jeans, you know? I like our 5-pockets specifically because they’re cut to be fairly ageless – they look great on a teenager but equally great on a guy in his 60s or 70s. Slim Straight. The name says it all.
Then, the sport coat. You want this to be on the more casual end of the spectrum, with some texture to it – a canvas, a high-twist wool, anything with linen or canapa or cotton. Our Monks Cloth would also be fantastic. It needs to feel knockaround, like it’s not too fancy to throw down on the barstool next to you. Something like a sharkskin wool is going to look too slick with a polo. In cooler months – not that you necessarily have those in Southern California – a corduroy jacket would be fantastic. See Dustin Hoffman in The Graduate for a great example. That was set in LA, wasn’t it?
And then last things last. For shoes, I’d do a pair of sneakers, not too pristine. (I’m super excited that we’ve got Tretorn Nylites back on the floor – those have been my go-to for most of my life, and definitely for this look in particular.) Maybe a pocket square, maybe not. Your call. I'd go without a belt; for some reason, in this setting and with the sneakers, a belt could feel like one toke over the line. To put it all together, here are a couple of combos you could try:
- Pale pink polo + natural jeans + chocolate Monk's Cloth jacket + white/white Tretorns
- White polo + stone jeans + lovat butcher jacket + white/white Tretorns
- Navy polo + navy butcher jacket + blue jeans + white/green Tretorns. Channel Harrison Ford with the mono-on-mono thing.
So that’s it. I’m hoping this feels like a simple – and maybe even confidence-building – solution. Every single one of the places you mentioned sounds like a great date to me. I'm not sure where you're located exactly, but I'm picturing the Belly Up Tavern in Solana Beach, which was pretty divey once upon a time. Give one or two of these a try and report back. And good luck… not that you need it.