Cheryl Shops

My love of black pants probably began when I was in college. I had a pair in a stretchy boot-cut polyester from Contempo Casuals, where I worked, and they made me feel very chic and grown-up. I wore them out to parties and bars, with going-out tops of course, or with a more demure sweater or blouse when I needed to look polished. Conservatively speaking, I probably own about 10 pairs of black pants at the moment, and yes, I wear them all. Some of them are skinny—a silhouette that I truly don't think will ever go fully out of style—some are straight leg, but what my closet has been missing is a true menswear-inspired wide-leg trouser. I've been searching for the right pair for awhile and have had some misfires, but I've finally found The One, and it's so good, I've been living in this pair for the last month or so. Styling wide-leg pants can be a little tricky, especially if your closet is heavy on longer tops (which look better proportionally with skinnier pants), but I'm here to help. Here's what I'm wearing with my wide-leg trousers.

Madewell Harlow wide-leg pant

I happened to impulsively try these on while I was in Hawaii and it was like the stars were perfectly aligned. These check all the boxes for me. The fabric is a lightweight, beautifully drapey Tencel-linen blend (and, bonus, you can machine-wash it). The leg is exaggerated but not elephantine. There are front pleats, but they're placed perfectly so they don't bulge out and make me look like I have a FUPA. The length is perfect—long enough to wear with a low heel but short enough to wear with a flat or a sneaker and not drag on the ground. The waist is definitely high and snug, but on me at least, it sits at the smallest part of my waist, and I think that's key to having the pants hang perfectly and complement your shape in the best possible way. Oh, and did I mention they're comfy AF? On the store associate's tip, I sized down to a 4 in these; I think if I had bought my usual size 6, they'd be too slouchy, possibly sloppy-looking. I am a little thicker through the middle, so if you have a tiny waist, you might even want to go down two sizes. Long story short: size down.

Everlane oversized blazer

Conventional wisdom would be to wear something cropped and fitted with such a voluminous bottom (like I did a few weeks ago) but as I always like to say, some rules were meant to be broken. Also, you don't always have to run out and buy a whole new wardrobe any time there's a silhouette shift like this. This oversized blazer actually works here because it helps balance out the high-waisted pants and make me look a little more in proportion—I have a freakishly short torso, so if I had worn a cropped jacket, this would have been painfully apparent. This blazer is one of my all-time favorite Everlane purchases; they've raised the price a little since I bought mine, but it's still a fantastic deal for such a classic investment piece. I also sized down in this one (I'm wearing a 4) as I feel like a blazer needs to fit in the shoulders, first and foremost. As long as it does, then you can go ahead and break whatever fashion rules you want to. 

Quince organic cotton boyfriend crew (get $20 off)

Again, conventional wisdom would tell you to wear something fitted with a voluminous pant, but it was actually a little chilly when we shot this outfit, so I wanted to layer a sweater underneath. This one is slightly cropped—I wouldn't wear it with anything low-waisted—but because I did want to flash a little waistline (and not look like a big blob), I did a half tuck in front. I am obsessed with this sweater; it's a nice, thick cotton that's perfect for transitioning between seasons, and while "boyfriend" is a bit of a misnomer (it's not long enough to be a men's sweater), it has a really cool slouchy shape. I'm wearing a medium, which is what I usually order from Quince; I probably could have gone with a small, but I think the hem might have hung strangely had I done that—there's almost a curved shape to it due to the wider body and ribbed hem. Full disclosure: I work for Quince, so if you have any questions about the brand, fire away ;) 

Vans Sk8-Hi sneakers & Balenciaga city bag 

As I said earlier, I love these pants because you can wear any type of shoes with them; in this case, I went with sneakers because we were going to wine country (and it was still too cold for sandals). I love how dressed-down they make the outfit feel; if I had worn a heel, this would have definitely read more work vs. drinking wine. And purse-wise, anything would have gone here, but my 20-year-old(!) Balenciaga city bag has been a recent favorite—guess Y2K fashion is back for me after all! 

OUTFIT DETAILS: Everlane oversized blazer | Quince organic cotton boyfriend crew (get $20 off)| Madewell Harlow wide-leg pant | Isabel Marant Lecce belt | Balenciaga city bag | Vans Sk8-Hi sneakers | Sojos sunglasses