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On My Mind: Big Shirts and Easy Spirit Loafers

Photo-Illustration: The Strategist; Photos: Retailers, Joe McKendry

My 2-year-old son started preschool in January, and the daily drop-off routine has become a refreshing source of style inspiration. More and more, I want to model all of my outfits after the way these toddlers dress — lots of pattern-mixing, long-sleeve tees with wacky illustrations, Velcro sneakers, princess gowns over pants, and balloon-y sweats. My translation of their approach to fashion is still taking shape, but the mood board includes a lot of overshirts, baseball caps, cotton or linen scarves, and summer-weight dresses worn over jeans.

I recently bought a vintage cornflower-blue corduroy button-down at the Park Slope Beacon’s Closet. It’s a men’s size large so it’s very oversized and falls just below my butt. It also has a strip of floral-print cotton on the inside of the collar, and I love it so much that I started searching for similar shirts in other colors and wider-wale corduroy. My go-to search terms for vintage clothing are always “Lizwear Sport” and “Bill Blass.” I own multiple items from both brands, and they fit me well and are consistently great quality with slightly off-kilter details.

Since it’s Jeans Month at the Strategist, I am also deep in self-reflection about the kinds of jeans I want to wear as I get older. I’m still wearing my Rudy Jude utility jeans at least weekly and have been pleasantly surprised by a pair of wide-leg jeans from Aritzia’s Denim Forum label. But my newest discovery, one that feels right in line with a “cool toddler” vibe, is this elastic-waist pair of wide-legs from Jungmaven. They are ridiculously comfortable and getting softer with each wash. I will be wearing them all spring and even attempting to layer them under a dress.

There is an artist and mom I follow on Instagram, @littlewifey, who makes stuffed horse-shaped pillows out of vintage fabrics. (I have yet to successfully purchase one before they sell out.) In addition to drooling over her handicrafts, I like the way she dresses in a sort of hardscrabble homestead-y way that is not twee. She recently posted a bunch of dresses-over-pants outfits to her Stories that made me want to try something similar. So far I have done it with a plaid Christy Dawn dress and a plaid pinafore-style dress from Toast, both of which are not currently available. But I think the look could work well with a lot of different dresses. I really love plaid ones because they feel neutral and remind me of school uniforms; Christy Dawn currently has quite a few on their resale site, and there are many on Poshmark and eBay in colors that are super wearable.

I bet these two dresses would look cool over jeans too.

Here’s everything else I’ve seen recently:

I keep seeing cool people with this cross-body sling from NYC brand Bags In Progress. First I saw it at a kid’s birthday party, worn by a close friend of Strategist writer Lauren Ro. Then I saw it on a woman walking near my son’s school in BedStuy. I have a bucket-style bag from the brand that I got almost a decade ago, and now I want more.

I’ve been slowly transitioning out of wearing Blundstones every single day. But it’s hard to wean myself off of the comfort they provide. So when I don’t want to wear sneakers, I have been wearing this pair of suede monk-strap shoes from orthopedic shoe titan Easy Spirit. I love that they have a chunky sole and look like Bucks without the same preppy connotations. Plus they are surprisingly light and bouncy.

It’s none of my business, of course, but I am not completely sold on Timothée Chalamet’s recent style transformation. And yet I do admire his dedication to lightweight scarves. They are practical, especially when it’s windy outside, and they look nice with almost any outfit. I own quite a few scarves, but the one I have been wearing the most lately is a men’s indigo plaid linen scarf that I got years ago as a gift. There is no tag, so here are a few similar options I like:

I am always folding laundry and then precariously stacking the piles on the floor or a dresser because I get too tired to put it all away. I’d like to find a nice-looking rectangular laundry basket to hold the clean stuff until I can get to it. So now instead of putting socks into drawers, I’m ogling the Steele Canvas website trying to decide whether I want a regular basket or one on wheels, with a wooden top that turns it into a table.

Photo: Liza Corsillo

My dog died in December. She was my constant companion for 14 years and just the funniest, best dog ever. I had been struggling to find a way to organize some of the keepsakes I have of her life. It took a while to find, but I like that this box frame lets me display my favorite photo of her while keeping her collar and a little lock of her fur tidied away until I am ready to look at it again.

We’re starting to give my son sandwiches for lunch and have been really excited about Dave’s thin-sliced bread. I personally prefer the balance of thinner bread slices for toast and sandwiches because it allows you to taste all the other stuff more. But it’s also easier for my son to eat.

The Strategist is designed to surface useful, expert recommendations for things to buy across the vast e-commerce landscape. Every product is independently selected by our team of editors, whom you can read about here. We update links when possible, but note that deals can expire and all prices are subject to change.

On My Mind: Big Shirts and Easy Spirit Loafers