the september edit.

Style
Written By ally m. rodriguez

there’s something magical about september in new york city. the air shifts, the light softens, and suddenly every sidewalk feels like a runway for the start of fall fashion.

This month’s trends are both playful and polished — imagine polka dots with a bold attitude, collared sweaters that perfectly capture that nostalgic “back-to-school” vibe, and plaid patterns in every imaginable form. Flat mules are making a stylish statement for chic commuting, and yes, knee-high socks are making a strong and fashionable return. Consider this your ultimate guide to what to wear, how to style each piece effortlessly, and (most importantly) the best places to shop these must-have looks.

Shop Fall Fashion Favorites.

1. polka dots with a twist 🎀

polka dots are having their moment this fall — bold, graphic, oversized. they instantly dress up denim or add a playful contrast to tailoring.

  • a polka dot blouse under a blazer for work

  • a dotted slip skirt with a cropped knit for brunch

  • a polka dot midi dress with knee-high boots for a statement look

shop the look:

2. collared sweaters & preppy knits 📚

back-to-school but make it chic. collared sweaters add polish with zero effort — you can throw one over jeans and still look styled.

  • layered over a pleated skirt for collegiate vibes

  • tucked into wide-leg trousers for the office

  • with denim and ballet flats for a casual day out

shop the look:

3. plaid everything 🖤

no september edit is complete without plaid. oversized blazers, mini skirts, and scarves are the backbone of fall wardrobes.

  • plaid blazer over a slip dress for instant edge

  • plaid trousers with sneakers for everyday chic

  • plaid mini skirt with a knit and loafers for prep revival

shop the look:

  • plaid blazer

  • plaid trousers

  • plaid mini skirt

  • oversized plaid scarf

  • plaid shacket

Featured
the september edit.
the september edit.

there’s something magical about september in new york city. the air shifts, the light softens, and suddenly every sidewalk feels like a runway for the start of fall fashion.

This month’s trends are both playful and polished — imagine polka dots with a bold attitude, collared sweaters that perfectly capture that nostalgic “back-to-school” vibe, and plaid patterns in every imaginable form. Flat mules are making a stylish statement for chic commuting, and yes, knee-high socks are making a strong and fashionable return. Consider this your ultimate guide to what to wear, how to style each piece effortlessly, and (most importantly) the best places to shop these must-have looks.

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End of summer dressing is truly a whole mood. It’s not quite the season to break out chunky sweaters just yet, but honestly… I can’t handle another full day in denim shorts without feeling like I’m melting away. The secret? Embracing transitional pieces that allow you to glide through these sticky, humid August days while still maintaining your effortless, cool vibe.

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fall fashion in NYC 2025: what to wear to look chic.
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Fall fashion in NYC isn’t just about staying warm and comfortable. It’s about telling a story—one where your carefully chosen outfit seamlessly carries you from a cozy Brooklyn coffee date to a chic art exhibit in Chelsea, and then straight into a dimly lit, intimate dinner in the East Village. Whether you're exploring uptown, downtown, or somewhere in between, here’s everything you need to know (and wear) to step confidently and stylishly into Fall 2025.

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4. flat mules (the chic commuter shoe) 👡

fall’s most practical yet chic shoe. flat mules look good with literally everything.

  • elevate jeans and a tee

  • balance wide-leg trousers

  • glide seamlessly from coffee run to dinner

shop the look:

5. knee-high socks, styled fresh 🧦

from cozy to chic, knee-high socks are officially back.

  • with loafers + a mini skirt = very fashion week

  • with oversized knits + sneakers = cozy girl energy

  • with mary janes + sheer socks = downtown cool

shop the look:

6. bonus september obsessions 🌟

  • ballet flats (mesh or ribbon details)

  • boxy blazers (slouchy, menswear-inspired)

  • mini bags (playful + impractical = perfect)

  • chocolate brown knits (this fall’s power neutral)

  • headbands & bows (lean into preppy polish)

shop the look:

how to mix it all 🍁

the magic is in combining pieces:

  • collared sweater + plaid trousers + flat mules = weekday uniform

  • polka dot skirt + oversized blazer + knee-high socks = city chic

  • slip dress + plaid coat + ballet flats = brunch outfit of dreams

Shop everything mentioned in this post here: https://shopmy.us/collections/2123698

Shop more of my favorite products here: https://shopmy.us/alessamrodriguez

final thoughts

September is for experiments — a vibrant month where layering suddenly feels fun and exciting once again, and trends become genuinely wearable. This carefully curated edit is your perfect starting point: think classic polka dots, cozy preppy knits, timeless plaid, effortlessly chic mules, and socks styled with unexpected attitude.

grab your pumpkin latte, slip on your mules, and step into september with style. 🍂

thank you for being here. always. 🕊️
— ally

DISCLOSURE: SOME OF THE LINKS IN THIS POST ARE AFFILIATE LINKS AND IF YOU CLICK THROUGH OR MAKE A PURCHASE I WILL EARN A COMMISSION. PLEASE KEEP IN MIND THAT I ONLY SHARE ABOUT BRANDS/COMPANIES THAT I ADORE VERY MUCH.

ally m. rodriguez http://www.maybeally.com
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september in nyc.