It’s basically the first weekend of fall, luckily, the universe has decided to be kind and ease us in with sunny, warm and only ever so slightly cooler weather. It’s also the start of the new season, with Sunday being the official start of fall and all, so if you’re back to spending weekends in the city like us NYC folk or not, you actually feel like taking the time to look cute and since you know that won’t last long, it’s the perf excuse to bring out the casual trends of fall. Then again, it’s also the end of NYFW, so if you’re in the fashionably blessed crowd but not headed to London right away, it means two days of flats (or in my case, bare feet), tees, jeans or other comfy pants (in my case, let’s just be honest and call them sweats, or mayyybee leggings if I feel like getting ~fancy~). Ahh, blessed. Either way, enjoy the good weather and break out something cute, because apparently winter is coming…
Flare Jeans + Sheer Top + Sneakers
If you’re going to be running around all day, a black sheer-ish short-sleeve top is perf for appointments that you want to look more polished for (like hitting up a store with judge-y sales people or brunch with judge-y friends, or meeting with a wedding planner, or whatever) and you can just swap in heels and a clutch to go out to dinner or drinks without changing.
Overalls + Tee + Loafers
Say what you will, I will never not get behind this trend. Overalls are genius because they’re unbelievably comfy, loose enough to hide your brunch (or in my case, vaca bulge), and look trendy. For daytime errands, you can throw a tee or sweatshirt under or dress up a tidge with a lace-y sweatshirt and add birks, sneakers, or loafers for polish. And if you don’t want the emotional trauma of trying on your jeans after an indulgent week (ahem), you can toss on a sheer shirt and heels to go out come evening. The best part is instead of looking schlumpy, you’ll score points for looking so fashionable and street style cool. Suckers.
Cropped Flares + Striped Tee + Espadrilles + Bandana
A striped tee and jeans is a classic weekend look that’s always chic. You can go cas in flip-flops or sneakers, or take it up a notch with espadrilles (you’ll probably be glad you went the sandal route, because as much as you may be excited to break out the fall shoes, it’s going to be a long time before sandal weather reappears). If you’re like me, and you are all about the classics and yet you feel so ~basic~ (yep, I said it and I hate me too for using the ‘b’ word but guess what? I’m over it. Basic, basic, basic….), thank the universe for blessing us with the bandana and whoever decided to make the $1 western party favor, an “it” accessory this year. Tie one on and suddenly your ~basic~ (oh yeah, there it is again) stripes and denim are so trendy and cool.
Army Pants + Sweatshirt + Sandals
Army pants are back. I remember rocking the baggy, cargo styles back in high school, probably with a crop top. (Aaaannndddd, I just found the name of my next book — Everything I Know About Fashion, I Learned in High School. Amazing and depressing at the same time.) But I much prefer Karlie Kloss’ updated take on the army green pant — the fitted joggers with a subtle nod to the cargo style at the top are comfy and cool and more polished than my early 2000’s look. A cute fitted sweatshirt keeps with the casual Sunday vibe, but the key to her look is so simple — finishing it off with a nicer pair of flat sandals. They’re still comfy and low-key, but whereas birks or sneakers would make it feel honestly a little schlumpy outside the house, her leather T-straps add a subtle polish that keeps you from feeling embarrassed if you run into someone you know while running errands.
Button-Front Denim Skirt + Sheer Top
Denim skirts make me feel too teen to me — probably because it’s all I wore as a teen. But the button-front style that was literally on every other showgoer at NYFW, feels like it could work on “adult” me. I don’t know why just adding a string of buttons to the front makes that big of a difference (or if it’s just a psychological thing for moi), but paired with a more sophisticated top, I’m loving it for a lunch date with flats, or Saturday night out with lace-up sandals or cage booties.
Cropped Flares + Knotted Men’s Oxford Shirt + Flat Sandals
For a boozy lunch or afternoon drinks with friends, or double date at a local spot, you want something that’s not as try-hard, souped-up as you’re typical going-out outfit but not as low-key as your usual brunch getup. Meet somewhere in the middle of the two by a button-up shirt and pairing cropped flares with non-basic (there’s that ‘b’ word again!) sandals (read: more special than simple black or nude or classic espadrilles, but not sexy python lace-up stilettos) that either have a low block heel or no heel. In other words, sandals that will earn you compliments but you can actually walk to restaurant in without having to take a cab back.
Cropped Jumpsuit + Tee + Chunky Sandals
Bonus points for a cute hat. A cropped jumpsuit in denim or a comfy jersey is perf for in-between weather and showing off cool sandals or sneaks. It’s casual with a tee for daytime, but still trendy. And with a crop top and heels, it’s super sexy for going out with the girls, or even a drink thing with bae.
White Jeans + Tee + Cozy Cardi + Printed Scarf
I love love love white jeans, especially when it’s not summer. I also love a comfy grandpa or long cardi as a weekend layering piece — it’s perfect if you suffer from hot/cold syndrome like me (translation: one minute you’re hot, one you’re cold, one you’re hot again…). If you don’t own at least one printed scarf, go to J.Crew immediately and purchase a few. (Pro tip: Just make sure the fabric isn’t itchy and feels soft against your neck, especially if your skin is sensitive like mine because otherwise you won’t wear it.) It blows me away how it’s so simple but how it instantly makes an outfit. It’s like you always invest in the bigger pieces like the jeans, the top, the shoes, but you can rock the most basic (can’t stop, won’t stop) of all those and look “so cute” just by throwing on a $10 final sale J.Crew scarf. Tbh, I don’t use this obvious style hack nearly enough, and then I end up being jealous when we bump into a wife of one of the hub’s friends looking so frigging cute (and feeling like a failure at life for spending an hour trying on a hundred different outfits just to go to the grocery store and ending up in a blah outfit when I could have looked “so cute” if I had just had a scarf that doesn’t itch wrapped around my ugh tee.
Ripped Jeans + Off the Shoulder Shirt + Loafers
I’m soo beyond obsessed with this look. It’s so hot but so cool because it’s not at all try-hard, and it mixes so many styles. It makes a sexier going-out top so nonchalant, a more boho style so urban edgy, and preppy loafers so… well, not preppy. It works for day whether it’s a fall Hamptons weekend, group birthday or otherwise, boozy brunch, or seen-and-be-seen city farmer’s market run, but I also like it for a date night or night out where you want to impress but don’t want to look like you’re trying to impress. Also, I’m just seriously obsessed with mom-jean style distressed denim, and equally obsessed with off-the-shoulder tops. I just find them so elegant and so hot, which is actually a rare and difficult combo to master.
Cutoffs + Bell-Sleeve Top + Sandals
I say rock those cutoffs as long as you can and like white jeans, I think they’re even chicer in fall. A bell-sleeve top is simple yet trendier than a tee, and basically the “it” top on the street right now. So it’s perfect for a casual dinner or brunch at the city’s hot spot. And the whole thing is loose and comfy, and yet fashion-forward, which is pretty awesome.