September feels a lot more like a New Year than January. January is more of a comedown from holiday excitement than a time of rebirth and goals. September has always been associated with “a new start,” from the days of First Day of School photos, Staples hauls, and routine switch-ups.
As a kid, I remember always trying to visualize myself in my new classroom with a new group of peers around me. Would I be sitting next to someone I liked? Would my teacher like me? How hard would the math be? But the things we envision and try to prepare ourselves for are never the issue. There's always some other thing we haven't even thought of. And too much envisioning can also psych you out and bring a negative, preconceived notion of what could otherwise be a good experience. For me, college was a great example of this. As the days got closer to move-in day, I began to anticipate hating it. TL;DR I did, and I transferred back to NYC for my sophomore year. And while I’m grateful it unfolded the way it did, I ruined it for myself by anticipating a negative experience.
Being prepared is one thing. It means you have a backpack full of new supplies, a new haircut that will give you confidence, and a backup tee in case you get ketchup on yours at lunch. But anticipation is a waste of energy. And, especially for overthinkers or anxious individuals (me), you must actively resist anticipating.
I recently stayed out longer than I thought I would, from midday until after dinner. That is deserving of two separate outfits. At the very least, my top and shoes should have changed. I wasn’t prepared for this. And the worst part—beyond my lack of footwear options—was that it rained. In a way, though, I'm glad I didn't anticipate it. I probably wouldn't have enjoyed my time out as much as I did if I'd been worrying about it.
Plus, it gave me a reason to think of this great list of rain gear for next time.
The Davek Mini Umbrella
I’ve linked to this little champ before. The size is the best part: it fits into a small bag. But it’s also durable! It has withstood those random wind tunnels you can walk into on a narrow NYC street. I have it in brown to match the majority of my fall wardrobe.
The Long Rain Jacket
A waterproof/resistant jacket you love is helpful as a top layer, even when the day starts dry, or to have in your bag for any random wind uptick or afternoon shower. I have had plenty of uselessly short raincoats and have learned that length is crucial. A waterproof/resistant trench coat or balmacaan are good because they don’t look out of place on a sunny but brisk day.
When lightweight enough, these jackets can be packed down as small as a BAGGU reusable bag (numbers 1, 6, 7, 9, 10).
The Waterproof Loafer
I first acquired a pair of rubber loafers when I was doing a market story on loafers in 2019 or 2020. I was shocked to discover such an incredible invention as a fully rubber loafer made for the rain. A leather loafer, especially with a rubber sole, generally does the trick, but these are great in serious downpours.
A waterproof shoe is excellent for morning commutes in the rain and makes the journey to work in the rain much less miserable. Some of these are true waterproof pairs (numbers 2, 4, 5, 7, 8, 9, 10, 11), and some are good in the rain but tend to be more water-resistant (numbers 1, 3, 6).
The Tall Rainboot (That Doesn’t Look Like a Rainboot)
Count this as one of your best fall investment pieces: a tall black rubber riding boot. It looks like an everyday boot—which will look great with mini or midi skirts or slim trousers tucked in—but is also suited for the rain.
I’m apparently on a Vintage Burberry kick for fall. You can find great second-hand ones.
The Waterproof Tote
A waterproof tote, whether it’s the bag you go out with or one you roll up just in case it rains, is handy no matter the time of year. I specifically recommend this woven recycled plastic tote from Lalo (there are various patterns and sizes) for use when it’s pouring, but you need to run out to get a half-gallon of milk. It’s sturdy, too, in case you decide to get a whole gallon.
The BAGGU and Calpak are water-resistant, not fully waterproof, but they still beat a drenched canvas tote or ruined suede bag. For the rest, throw your belongings inside and cover them with an extra produce bag. Thank me after your next soggy grocery run.
The Hair Bonnet
Nikki Kule, the founder of the brand KULE (where I work as Content Director), suggested we get these for a shoot once, and I’ve kept one in my bag ever since. They’re inexpensive and reusable, and while six come in a pack, you can wear the same one many times (mine is still pristine after many wears). It’s an excellent little piece of rain gear to keep folded in your bag. Beats covering a fresh blowout in a plastic bag.
The forecast calls for rain this weekend…stay dry out there!
xo
Eliz