Back to School, But Make It Fashion: 7 Teacher Staples I’m Actually Wearing This Year
It’s my last week of summer break, and for the first time in my 23 years of teaching (!!!), I went into my classroom early. I’ve never done that. Ever. But something about this year feels different — hopeful, maybe. Or maybe I’m just trying to get ahead of the chaos. Either way, I’ve been prepping both my classroom and my closet, and after years of navigating Alaska weather, busy mornings, and a body that’s changed with age, stress, and hormones, I’ve finally nailed down a set of staples that actually work.
They’re comfortable, layer-friendly, and — dare I say — stylish. So whether you’re a teacher like me or just someone trying to dress for that “back to it” energy, here are the 8 pieces I’m reaching for again and again.
1. A Go-To Blazer
It instantly makes you look polished, even when you were up late redoing seating charts or binge-watching Real Housewives. I usually go for a relaxed fit in a neutral tone. It layers beautifully over a tee, tank, or even a sweater.
2. Non-Distressed Denim
Keep your rips for the weekend. A solid pair of dark or medium-wash jeans can take you from classroom to Costco without feeling overdressed or sloppy. My favorites strike that perfect balance between structure and stretch.
3. Athleta Black Pants
These are the magic pants. They’re comfy , structured enough for work, and they somehow never wrinkle. I’ve been wearing them on heavy rotation, especially on days when I want to look like I tried — without trying too hard.
4. Sneakers That Match Your Vibe
Whether it’s a neutral pair or something with a pop of color, sneakers are it. I wear mine with everything from jeans to wide-leg trousers. You don’t need to kill your feet to look put-together — we’re done with that era.
5. A Lightweight Cardigan
Cardigans are my year-round MVP. I have them in stripes, solids, cropped, long — and from just about everywhere, from Target to Quince to Abercrombie. I keep the ones I love and update with trends each season. The one I’m showcasing right now is from Quince, and it’s perfect for those moments when the AC is working overtime or you just want an extra layer without the bulk.
6. A Big Tote Bag
Right now, I’m using my Longchamp Le Pliage Large, and while it has zero structure, I love it. It’s waterproof, durable, and has been with me for years — from daily use to travel days. It’s a true carry-all that fits everything, but fair warning: with no built-in organization, things can disappear in there. You can find tote organizers on Amazon (hit or miss, in my experience), but honestly, I just love it for what it is — dependable, roomy, and ready for anything.
7. A Belt That Pulls It All Together
A simple belt can totally elevate your look. It defines the waist, adds intention to your outfit, and makes jeans-and-a-tee feel like an actual outfit.
Final Thoughts
I didn’t always feel good in my clothes — especially as my body changed. I’m 45 now, and between stress, hormones, and life, I’ve learned to shift my focus from “what size am I?” to “how do I feel in this?” And I’m not alone. A follower recently messaged me and said:
“Yes, I've really appreciated your body positivity and the way you embrace what life brings... Our generation grew up in diet culture where being skinny was always the goal, when in reality it's about being healthy — physically, mentally, and emotionally. I find myself going through so many of the same changes and it can be tough at times, but I truly love your page and feel blessed to have met you a few times. Keep being you. That's what is truly valuable and inspiring.”
That’s what I hope to bring to you here — inspiration to dress in a way that feels good on the body you have right now. Because you deserve to feel confident and stylish at any age, at any size, and yes… even on the first day back at school.
XO, Lesli