I really do think the advice to start with shoes is very sound. Pick 2 pairs that you can walk in and make sure everything will work with either pair.

If you're going to a show, he could wear jeans or khakis with a button-down shirt, but sneakers would still be fine. Something like this:

https://www.gap.com/browse/product.do?pid=416208002&vid=1&tid=gppl000062&kwid=1&ap=7&gad=1&gclid=CjwKCAjwtuOlBhBREiwA7agf1k4ZWmEuzrEIAr-EnT7Eej7etFFtBMLF_7rtXr9bnBUNeiIWyK9IbxoCLSAQAvD_BwE&gclsrc=aw.ds

And you could wear something like this with a cardigan:

https://www.gap.com/browse/product.do?pid=665882012&cid=13658&pcid=13658&vid=1&cpos=36&cexp=2859&kcid=CategoryIDs%3D13658&cvar=25416&ctype=Listing&cpid=res23072018779180794385811#pdp-page-content

OP here. Thank you PPs! Love the suggestions. Yes to good shoes and weather-appropriate clothing. I’ll check out the links and recommendations.

Anonymous wrote:Check the weather - jeans in NYC in August might not be such a good idea

I was just there - wore lightweight dresses with sneakers - like this one
https://bananarepublicfactory.gapfactory.com/browse/product.do?pid=628540001&cid=1181673&pcid=1045225&vid=2&nav=meganav%3AWomen%3AWomen%27s+Clothing%3ADresses#pdp-page-content

This dress is cute!

I go to NYC often and was just there a few weeks ago. I wore a midi-length black slip skirt, slightly cropped graphic tee, and comfortable sneakers. If it's cooler, I wear jeans in a current cut with a button down shirt and roll the cuffs up - either sneakers or boots depending on the outfit. Avoid shorts unless you are very young and tall -- I rarely see anyone over 25 wearing them in NYC unless they're working out. No capris or sweatpants.

My teen boy wears jeans or athletic pants with a hoodie no matter what the weather. Never been an issue in NYC, even in restaurants/theaters. Obviously I'd rather he dress a little nicer but I choose not to ruin my vacations with him fighting about clothes.

Check the weather - jeans in NYC in August might not be such a good idea

I was just there - wore lightweight dresses with sneakers - like this one
https://bananarepublicfactory.gapfactory.com/browse/product.do?pid=628540001&cid=1181673&pcid=1045225&vid=2&nav=meganav%3AWomen%3AWomen%27s+Clothing%3ADresses#pdp-page-content

Bootcut jeans, linen tops and tees, comfortable shoes, and you’re good to go. NY has gotten very casual since 2020.

I think you have to start with what activities you’re going to be doing and the weather.

Nobody looks chic or confident soaked in sweat, sunburned, with blisters, or with chub rub.

It’s far better to be underdressed or unfashionable than to have any of the above happening. If you’re going to be walking a lot in August, you have to do utility first.

Cotton sun dresses for you. Tees and regular shorts for your son.

Whatever you do, avoid capri pants.

I am in NY all the time and can say it’s a lot less fashionable these days… for your trip, focus on a good pair of well-fitting jeans, sneakers like Vejas, a linen top, some cute tees, and a big breezy scarf that can add some flair. If you can pull off a long skirt or maxi dress that will take you far as well.

Start with comfortable shoes.

Anonymous wrote:

Anonymous wrote:The best past about NYC is that nobody cares what you’re wearing. It’s crawling with tourists too.

Bring clothes that are comfortable for the weather and your planned activities. Also shoes that you can walk many miles in. Sandals are fine for dinner, but NYC is dirty, so I like to have my feet covered.

OP already spent her time during covid wearing only comfortable clothes. You're making it sound as if looking good must be uncomfortable.

My point was more "don't over think it". Definitely get some new stuff before your trip so that you feel good. But also, if you are going in August it's going to be hot and sticky so don't overthink trying to be trendy.

Hi Op -

I would definitely focus on what you are comfortable in and not stress too much.. simple, capsule type clothing will make it easy to mix and match. Some specific ideas to get you started below..

Veja sneakers:
https://www.freepeople.com/shop/veja-campo-sneakers/?color=011&countryCode=US&gclid=CjwKCAjwtuOlBhBREiwA7agf1j-q3f3_aCB1J2T40KrXrzRJPD1JnQJXbjo9SRqvZRBLWlH50S2IKxoChPQQAvD_BwE&gclsrc=aw.ds&inventoryCountry=US&size=EU%2037&utm_kxconfid=vx6ro62gj

Button up shirt worn with either linen pants/ shorts or cutoffs:
https://www.madewell.com/eyelet-button-up-camp-shirt-99107081062.html?
noPopUp=true&srcCode=Paid_Search|Shopping_NonBrand_SSC|Bing|MWGGBS00002&gclid=9cc755e0ca031c710f2531598e246b17&gclsrc=3p.ds&msclkid=9cc755e0ca031c710f2531598e246b17&utm_source=bing&utm_medium=cpc&utm_campaign=Madewell_Shopping_PLA_SSC_US_Womens&utm_term=4580634174995501&utm_content=Ad%20group%20%231

Linen shift dress for dinners;
https://emersonfry.com/collections/shop-all/products/high-neck-short-dress-ivory-linen

Easy breezy dress because it is going to be hot!
https://www.madewell.com/poplin-cutout-back-empire-midi-dress-NL442.html?dwvar_NL442_color=BL6198&dwvar_NL442_size=0&cgid=apparel-dress-midi#intcmp='Dresses_VisualNav2_Wmidi&start=27

Sets from Amazon like these.. comfortable but look polished.
https://www.amazon.com/ANRABESS-Outfits-Matching-Vacation-997heise-S/dp/B0C1NW5SF6/ref=sr_1_5?keywords=matching+linen+sets+for+women&qid=1689863004&sprefix=matching+linen+set%2Caps%2C151&sr=8-5


https://www.amazon.com/AUTOMET-Matching-Tracksuits-Vacation-Jumpsuits/dp/B0BWXM8GJQ/ref=sr_1_6?keywords=matching+linen+sets+for+women&qid=1689863028&sprefix=matching+linen+set%2Caps%2C151&sr=8-6

And then I would add in flat leather sandals, a comfortable cross body bag, gold hoops and layered necklaces...

Anonymous wrote:The best past about NYC is that nobody cares what you’re wearing. It’s crawling with tourists too.

Bring clothes that are comfortable for the weather and your planned activities. Also shoes that you can walk many miles in. Sandals are fine for dinner, but NYC is dirty, so I like to have my feet covered.

OP already spent her time during covid wearing only comfortable clothes. You're making it sound as if looking good must be uncomfortable.

The best past about NYC is that nobody cares what you’re wearing. It’s crawling with tourists too.

Bring clothes that are comfortable for the weather and your planned activities. Also shoes that you can walk many miles in. Sandals are fine for dinner, but NYC is dirty, so I like to have my feet covered.

Extremely unfashionable current Midwesterner here, traveling to NY with teen son in August. It's been a couple of decades since I lived in NY and my fashion sense seems to have left me around the same time (20+ years in the workforce at rather straight-laced/non-creative employers/industry). So: I'd really appreciate a quick overview of what would constitute acceptable fashion for visiting NY without looking like...well, what my kid and I look like in usual our day-to-day. What are the late 40s women wearing? What about an older teen old boy who's been told he can't travel with 100% athletic wear? We are pretty much starting from scratch head to toe. Between covid-related work-from-home (me) and a massive growth spurt (him), we could use some new clothes anyway. Thank you in advance!