#2192 How To Spend 48 Hours In New York City

Tony Curtis in a good shirt and tie. Photo: GQ

What do you think are the best ways to overcome post breakup anger/sadness and feelings-of-outrage?

I’m a firm believer in cutting all contact with the ex in question – delete them on Facebook, stop hanging out with their friends, don’t go to places where you know they’ll be, never, ever drunk dial them; but most importantly, try not to spend all your waking hours dwelling on them. Self-preservation is key. Nobody else is going to look out for you, you have to look out for yourself. Focus on the positives in life – forget how happy your ex seems to be or how they’ve gotten straight into another relationship or how they didn’t have to deal with any consequences for being such a jerk. Throw yourself into your work, exercise, friendships etc. Volunteer at the City Mission. Do whatever you can to take your mind off the break up. And for God’s sakes, don’t let it be the only thing you ever talk about with your friends. They’ll end up wanting to break up with you too. Best of luck.

Hey Isaac! So, I’m turning 21 this year. My Mum has agreed to buy me a suit as a present. Here’s what I’m thinking: navy blue, single-breasted, two-button. Just something classic and simple; maybe throw in some brown brogue oxfords. Thoughts? More importantly: where should I look? And should I purchase an off-the-rack one and get it tailored, or go straight to made-to-measure? Nothing fits me off-the-rack ha. And…what collared shirts should I go for?

You’re a lucky chap! I’m going to give you a couple of options in different prices because I’m not sure if you’re looking to spend hundreds or thousands, but here goes: I went to J Crew this afternoon and tried on the Ludlow suit jacket and it was amazing straight off the rack. (I, like you, don’t usually fit off the peg suits.) Right now, they’ve got a tone-on-tone navy glen plaid that is beautiful but kinda pricy – you’ll get the whole suit for about $900, or a plain navy that you can get for $620. Buy it, and take it straight to your tailor – tell him to nip it in at the waist, slim down and shorten the sleeves (depending on whether or not you’re showing your requisite quarter inch of shirt cuff), taper the pants and get them cuffed above your ankle. That’s what I’d do anyway. Those alterations will probably set you back an extra $100 – $150.

If you really want to go all out, go made-to-measure. You’ll end up spending at least $1500, but it’ll literally be the most fun you’ve ever had (with your clothes on or off). Right now if I could get one from anybody, I’d choose Sid Mashburn or Ovadia & Sons.

I’d get these brown brogues by Loake.

I wear button down shirts 90% of the time, so that’s what I’d recommend. J Crew does a great selection or you could get them from Uniqlo on the cheap. You should probably throw in a couple of ties too – GQ‘s got you covered for that one. Wear them like TC above.

Girls in navy corduroy?

Yes. That was easy!

Isaac, I’m coming to New York in June and have only two days there. I’ve been before when I was younger (am 20 now) and I’ll be staying with a New Yorker but what’s your recommendation for a 48 trip? Given how small the world is, I’ll probably recognize you in the meatball line…   

Here’s an email I sent to a lovely girl named Larelle last week:

I hear you’re coming to New York City! That is very exciting indeed. I’ve never loved a city more in my entire life.

Here is a list of places to go, and things to do. Make sure you do everything on this list!!

1. Eat the daily special at The Meatball Shop in Williamsburg, then the ice cream sandwich for dessert. Choose peanut butter for the cookies and chocolate for the ice cream. It’s the best! Trust me!

2. Get the avocado on toast at Cafe Gitane. So good.

3. Get either the chicken quesadilla or the pulled pork sandwich at Cafe Habana (it’s where Justin Timberlake and Mila Kunis eat in Friends With Benefits).

4. Walk the Williamsburg Bridge!!!

5. Go for a drink at the Boom Boom Room or Le Bain (both are at the top of The Standard Hotel) at sunset. Best view EVER!

6. Go to karaoke at The Woods in Williamsburg on a Tuesday night. Most fun ever!

7. Walk the Highline! Do that before you go for the drink at The Standard.

8. Go to MOMA and The Met! Look at some amazing art! But not too much. You’ll get all tuckered out.

9. Party at Darby and One Oak! So much fun.



share on TumblrShare on FacebookPin on PinterestTweet about this on Twitter


  1. Guest says

    Isaac, you gave me similar advice for NY about two weeks ago when I asked you about hostel locations. I managed to do pretty much everything on that list besides MoMa and The Woods. Gitane were in fact very delicious, as well as the bolognese meatball sandwich and balsamic strawberry ice cream sandwich (specials of the day). Le Bain was fun and the view from the rooftop was amazing. I met an awesome girl who was working there so I have to thank you in double for that one. New Yorkers were super nice all the time and now I understand why you love the city so much.

  2. Guest says

    Just in regards to shirts with suits, for slimmer dudes looking for great fitting office / business shirts in NZ, the Working Style Engineered Fit shirts are amazing and the best I’ve found. Really nice double-folded button cuffs too, great cotton and they wash really well. They’re quite pricey at the actual WS shop (around $250?) but if you go to the outlet store you can get em for $150 and sometimes cheaper.

  3. Sus says

    I have now been and gone (but I’ll be back) and managed to tick off a few on the list. Highline was awesome, Met was neat and got the amazingly delish corn from Habana. Tripped over to Williamsburg too, and it was such a quirky place. Unfortunately I am not yet 21 (soooo close) so I’ll have to save the Boom Boom Room till next time but based on the name alone it sounds spectacular. Great advice as per usual, my dad got sick of me saying ‘ooh Isaac recommended that’ or ‘I hope I run in to Isaac somewhere’… Thanks!

Leave a Reply

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