I have about a dozen sweaters. In an effort to appreciate them more and avoid buying new ones, I did a shop-my-closet, try-on session recently. It really helps me to pick out items I don’t usually wear and also pair them with things that I wouldn’t usually choose. I find that makes getting dressed in the winter more fun. Here are a couple of outfits I felt pretty good about.

J Crew sweater | Madewell jeans | Madewell boots

This thin, cotton, almost a shirt sweater is so old but doesn’t look it. It’s dark navy blue and goes with everything. I’m wearing it with an old pair of Madewell boy jeans that I recently patched the knee on. I had them up on Poshmark to sell, but have been thinking of keeping them. And then I’m wearing an also old pair of brown swede Madewell boots.

 

GAP sweater | Everlane jeans | Docs

I love this forest green GAP turtleneck. I went with a 90s off-duty model look by tucking it into my new Everlane 90s cheeky jeans and black Doc Marten boots. Not sure this is me, but it kind of works.

Everlane sweater vest | J Crew skirt | Troentorp clogs

I got this sweater vest recently at Everlane and I love it. Wearing it without a shirt underneath would probably not happen in real life but I thought it looked cool. The whole mini skirt and tights combo is another thing that is outside my comfort zone. With the clogs, I feel very Scandi. I threw a black wool jacket over it and kind of liked that too.

LL Bean sweater | Leather pants | Birkenstock Bostons

Loving this fishermen’s sweater so much. I tried it with some leather pants I thrifted last year. An amazing find! And then I chose my Bostons, which seemed an odd choice but looked pretty cool.

J Crew sweater | J Brand jeans | Lotta’s clogs

This J Crew sweater is a navy V neck that’s also an old fave. The jeans are thrifted. I haven’t worn them yet. I don’t usually go for the bootleg style, but they’re very flattering. I like them with a high heel like these brown clogs.

LL Bean sweater | Nili Lotan pants | J Crew rain boots

I got this green cashmere sweater from LL Bean last Fall and it’s so nice. I picked the khaki chinos to go with because the two greens seemed almost clashing, or too matching. I don’t know. The rain boots are old from J Crew.