I have to say, upstate New York is very serious when it comes to not allowing warm weather to overstay its welcome. October 1st felt like the beginning of handwarmer weather.

My mornings now begin in the mid-40s to mid-50s so I already know that by the end of the month, I'm going to be layering tights 🥶.  But I enjoyed this outfit.


Wearing a jumpsuit at pants? Yes, please!


Except for when I need to use the bathroom. No, thank you.
I stressed myself out at the end of the day (you know teachers rarely get bathroom breaks) when I had to literally strip for a tinkle.


What I'm Wearing
Leather & Knit Jacket - maurices (thrifted)
White Box Top - chicos (thrifted)
Olive Green Striped Jumpsuit - Flying Tomato (purchased at Marshall's)
Nude Flats w/ Wooden Heel - Zara
Tan Patterned Headwrap - gifted
Earrings - F21

see October Capsule Post for similar items

Now, this outfit is brought to you in part by my sister, Sarah’s items (both the top and skirt) that I found when rummaging through bins of clothing and fell in love with.


If you're reading this sis, I will be returning them on November 1st. I love you and thank you.

On this day one of my students said: “Ms. U, you always have the nicest outfits and the coolest headwraps.” A comment that touched my heart, of course.


This headwrap is the printed button-up I chose for the month. I didn't plan to wear it as a headwrap but I couldn't figure out how else to incorporate it into my look and I just knew I wanted it as my print. So, this is the lemonade I made from that lemon.

What I'm Wearing
Printed Headwrap - Loft button-up (thrifted)
Earrings - F21
Necklace - F21
Olive Ribbed Top - F21
Paperbag Waist - Who What Wear (thrifted)
D'Orsay Flats - Franco Sarto
see October Capsule Post for similar items

When I chose the items for today's outfit, I did not consider exactly how I was going to put them together. So, on a whim, I decided to wear the cropped sweater inside my black dress (pinafore style) and, I must say, I love the look. Very school uniform :) which is incredibly fitting since I work at a school where uniform is required.


These earrings also gave me the opportunity to mix my headwraps in such a way. I love them. So much. Every Friday is “Red & Black” day at work, but this month, because of the colors I chose, every Friday will be burgundy and black day.


What I'm Wearing
Headwraps - Leopard H&M Scarf & Burgundy Pashmina
Earrings - F21
Cropped Sweater - BCBGMaxazria
Black Dress - NY&C  (thrifted)
Belt - (thrifted)
Mary Jane Pumps - Franco Sarto
see October Capsule Post for similar items

*In honor of a second-grade student that we lost to sickle cell anemia, all educators wore burgundy to school. In addition, we raised over $500 collectively to donate to sickle cell awareness and research. Look how good my team looks!

I woke up to a 36-degree day 🥶 ! I had to wear an extra layer of “skin” before getting dressed.



This extra skin is my key to staying warm while staying cute. It's literally just a tight-fitting tank top and fleece-lined leggings. Insulation is important for Upstate NY Fall and Winter survival.

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As for my spending, I'm doing great! I haven't spent money on anything other than the necessities (food, shelter, transportation, etc.) See you soon with looks 6 through 10!