I have spent the last several months (and by “several” I mean “since October”, so…SIX??) trying to figure out what my go-to boots were going to be for winter. And now that it’s Spring, which means means mud, mud and more mud (at least up here in Vermont), I’m finally able to say yes, here they are, confirmed: Doc Martens!
What? You don’t care? It’s too late?
Fine.
But! If you, too, are a Northern girl dealing with your fair share of mud, or you find yourself trying to navigate freezing mornings and beautiful, sunny afternoons…this is for you. I put together 5 cute-enough outfits perfect for these shoulder seasons, all featuring near-foolproof layering pieces and my most-worn, go-to combination: easy, loose jeans + mud-and-muck-friendly Doc Martens.
jacket (s) – keep reading for similar options | jeans (27) – also here | boots | bag
Where To Buy Doc Martens Leona Boots
If don’t have a pair to dig out of your closet, or you’re really charmed by the ivory pair I’m wearing (it’s allllmost a blush-colored hue), here’s a few places I found my fav Docs:
Nordstrom (black) | Nordstrom Rack | Amazon | Zappos | Free People
In Case You Care About My Jeans…
They’re by Re/Done, I bought them a little slouchy AND I love them with the passion of 10,000 suns. But I sat on something (nail?) and now there is a hole in the butt. SO I just did a deep dive into finding another *exact* pair.
Aritizia | Bloomingdales | Free People (faded black wash only) | Shopbop
Let me know if I should embark on a quest for similar pairs (since I basically never want to wear anything else).
It’s Cold, It’s Warm: 5 Layered Outfits For Tricky Transition Weather
The best transition outfits always involve some sort of strategic layering (duh). And while this approach seems fairly simple, layering is something that often works better in my head than it does on my body. Getting the layers right (aka comfortable and cute, each layer able to stand on its own) is actually pretty tricky, and, I’ve found, is completely piece driven. Which means, (to quickly summarize): not all t-shirts layer well!
And not all sweaters go over tops!
And not all jackets work with sweaters!
Etc.
1. Start Here: The Best Layering Tee Of All Time
top (s) | jeans (27) – also here | boots | bag
This long-sleeve tee, from Negative Underwear’s ‘whipped’ collection is one of the best layering tees I’ve ever found. It’s impossibly soft, thin, and a little sheer (without being overly so). It layers under sweaters with zero bulk, yet is pretty enough to wear on its own – although I usually wear a prettier bra or even a larger sort of bralette underneath it – pick one whose lines can show.
sweater (s) | top (s) | jeans (27) | boots | bag
Unlike other tight tees, this one – thanks to Negative’s truly unique fabric (91% Micro Modal 9% Lycra) – actually has some give, so while this tee has a fitted look, it’s not tight, and the extra length almost functions as ruching. I especially love it under a swingy little cashmere sweater (like my Everlane one, above), with the sleeves pushed up to better show the tee.
2. Try This Combo: Sweater Vest + Tee
sweater vest (s) | tee (s) | jeans (27) | boots | bag
Another layering trick I’ve been using is to swap out my usual cozy sweater for a vest. I love how vests look with a simple short-sleeve tee peeking out, and I can lose the vest if the day really warms up.
But the star of this show, actually, is this jacket:
jacket (4) | sweater vest (s) | tee (s) | jeans (27) | boots | bag
This jacket is made from a really soft wool blend, and it’s been juuust the thing to get me out of my usual puffer jackets. It almost functions like a tailored cardigan – it’s that soft. But the reason I think this piece is such a special find is because it’s also roomy in and under the arms. So it actually fits comfortably over sweaters and/or hoodies! Plus the color is very, uh, muck-friendly. I’ve even walked the dog in it.
3. Practical & Pretty: Fitted Cardigan + Barn Jacket
sweater (s) | jeans (27) | boots | bag
I’m loving the cardigan-as-top thing lately. I’m still wearing cashmere cardigans (it’s fairly cold up here), but my plan is to switch to cotton cardigans as the temps warm up a bit (this one from Banana looks especially cute over a tee).
sweater (s) | jeans (27)| boots | bag
I especially love how these ladylike pieces look when paired with a canvas barn or chore jacket.
jacket (s) | sweater (s) | jeans (27) | boots | bag
These are such shockingly versatile jackets (I’ve been drooling over them ever since Abby sported one in Paris), so here’s a few more I think are worth considering:
4. Too Hot? Try This: Pretty Denim Top + Barn Jackets
top (6) | jeans (27) | boots | bag
When skies are blue but the ground is mucky, I love a cute lil’ denim top. These pieces have enough heft to make sense with serious boots, but they’re still plenty cool (thank you, 100% cotton)
Of course, to warm this outfit up for early morning (or late night) temps, add any ‘ol cute jacket. I’m still not over this one, so.
jacket (s) | top (6) | jeans (27) | boots | bag
Happily, denim tops seem to be a thing right now, which simply means there’s a LOT to choose from. Here are a few that I personally like:
5. Still Cold? Just Lighten Up The Palette With Soft Browns
sweater (s) | jeans (27) | boots | bag
Finally, on days that I just can’t warm up (there’s something so bone-chillingly cold about a damp cold), I’m wearing my usual winter uniform, but swapping out my go-to black sweaters and coats for something in a really pretty, soft, brown. Or, if we’re being very 2025 Pantone about it…mocha mousse.
jacket | sweater | jeans | boots | bag
I do love layering not-quite-matching pieces for an almost monochromatic moment. Strikes me as irreverently cool.
Anyway. That’s what I’m actually wearing these days. Dreaming of swimsuits, but still wearing…ski gear. Aka: March.
xo,
S
