September is Coming… My Favorite Back-to-School Inspired Outdoor Gear

by | Aug 28, 2019 | Gear, Lifestyle, Women Specific

Because who doesn’t love B2S? Seriously, back to school (despite not being in school) is one of my favorite times. I feel like it’s a holdover from adolescence when September was more like the New Year than January 1 ever was. I’ve said it a million times, I always spent my family vacation thinking about back to school, and I was Kondo-ing my closet before it was cool. At the end of every August, before school started, I would take EVERYTHING out of my drawers and closets and pile it in the middle of my room… Then I would reorganize and put it all back. A little obsessive for an 8 year old but it’s set me up well for adulthood. But really, the allure of new pens and notebooks and filing systems were what got me excited. That, plus maybe a back-to-school outfit or two. Shallow, yes. Satisfying, also yes. So, here are a few of my absolute favorites if you’re craving that back-to-school vibe right now—to gear up for an outdoors / adventure-filled / athletic fall:

XC-running inspired kit

Not sponsored, just obsessed… with Tracksmith. I really love the vintage-y vibe, and I feel like it’s the first running brand that feels like it’s the aesthetic I’ve been looking for. Neutrals, slightly old-school, comfortable and really high quality. I’m super into the Van Cortlandt Shorts and this Fells Henley for a back-to-school feel (they’re currently out of the henley but this long-sleeve is similar!).


I do all of my to-do listing in the ToDoist app and on Peter and my shared calendar, but I LOVE a weekly planner for thinking things through. Lately, I’ve been in the habit of using one for a quick journal entry in the morning highlighting the 3-4 things that I really want to get done that day (stuff that will move the needle, not the little nagging to-dos that get on the master todoist list) plus a few sentences about what happened the day before/stuff I’m thinking about. I find a weekly planner is great for that since it limits the space you can write so entries are short and to the point and you don’t feel like you need to write a novel, but because each day has a space, you also are less inclined to skip a day like you would in a plain notebook. I also use this to write a quick note about my training for the day and how I’m feeling, so I can look back and re-assess. I love a simple gray or black planner, obviously, and it has to have spiral binding so I can lay it flat to write/see it throughout the day. I waffle between wanting bigger or smaller, and right now I’m into the 8.5×11 size but this one also comes in 5×8 if you prefer smaller.

Get it here (for $8!)

Tote bag

I was going to put a backpack, but I’ve talked ad nauseam about my two favorite backpacks on here already (Ortlieb and Timbuk2) so I wanted to put the new tote bag up. I’m fairly tote-bag-obsessed, since they’re so multi-purpose for work/errands/packing/grocery shopping and so on. I almost always have at least two with me when I travel, one that’s more structured and more of a purse, and one that’s foldable and can be crammed into my duffel and pulled out for grocery shopping or as a beach bag. This Ride Bikes Get Rad tote bag zippers (key for me!) and is pretty much the perfect gym bag/post-ride bag for your changing skirt and snack/work bag/library book bag/etc.

Get it here

Gym class sweatpants

Finding a pair of sweatpants that fit loose but not too loose, have a comfortable waistband, have the gym-class-style bands at the ankles for easier walking/not soaking the bottoms of them, won’t stretch and sag after one use, stand up to a billion washings, are airplane-stylish (i.e you can wear them in an airport and feel reasonably put together) and are, if not run-able, then jog-able, is honestly a really fricking tall order. I’ve bought dozens of pairs over the years and hadn’t found a pair that ticked all of my boxes until recently. Now, I really love Tracksmith’s sweatpants and just grabbed them in their sale, but since they’re out of stock, I admit I also have my eye on their Session Pants, which kind of blend leggings and sweats together

Sweatshirt + collar

I owe my mom big time for this one, but I LOVE a collar under sweatshirt situation, but really hate the bulk of a button down under a sweatshirt. ENTER THE DICKEY. Super 60s/70s, but so good. I 110% would have rocked this with skinny jeans and Converse when I was in high school and I will still be wearing it a ton this fall. I feel like the collar just adds a bit more polish to a sweatshirt and makes it more of a fashion choice versus a cozy choice… but the collar-only means that the sweatshirt itself is still cozy and comfortable AF.

Get the sweatshirt here and the collar here

Athlete-friendly jeans

I am not great with regular jeans. I have bigger calves thanks to running, and I have a sensitive stomach that’s prone to flare-ups that make me feel bloated and like I can’t stand to have anything compressed. So I rarely wear jeans, but occasionally, I do need to actually wear pants that have pockets and are a bit more legit than leggings or sweats. Enter the Old Navy High-Waisted 24/7 Rockstar Super Skinny Jeans. I’ve mentioned them before but I love them because they actually look like normal jeans but feel like sweatpants while still having an actual zipper and button plus REAL POCKETS in the front and back! I own a lot of pairs of pants that I don’t wear as often as I should, but these are the ones I always end up putting on when the need to wear real-ish pants comes up.

Lunch boxes accessories

Remember picking out the perfect lunch box as a kid? Were you more the ‘in-cartoon of the season’ type? I waffled between those hard-plastic lunch boxes that touted whatever I was into at the time and the more ‘grown up’ fabric ones that were plain black. Honestly, even thinking back to those ‘hard decisions’ choosing the right (but still budget-friendly because we weren’t a Jansport family!) lunch box gives me such a nostalgic pang. Who did I want to be in the lunchroom? The sophisticated fifth grader who was above cartoons and such childish endeavors, or did I want to show off the Batman logo? Very tough call for a 10-year-old. NOW, though, the adult version of this is choosing some accessories for your lunch kit. My current what’s-in-my-bag includes two new things for this year: reusable silicone baggies and a stainless steel straw. It’s a minor nod to being eco-friendly, I know, but I am trying to cut down on waste when it comes to food on the go, and I admit, I’m the kind of person who loves a straw. I thought adjusting to the stainless steel one would be weird but I kind of love it!

Get a straw and silicone bag set (plus reusable produce bags) here


In addition to a planner/daily journal, I always have a super simple small notebook on hand. I bulk-bought some when we were in Belgium a couple of years ago, and I’m just starting to hit the last couple of them—I keep one in my tote bag everywhere I go for brainstorming, listing, planning, plotting, etc.

Get a 12-pack of similar ones here

Let me know in the comments—what’s on your back to school list?


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