Cheryl Shops

Trends come and go, but one of the benefits of being a woman of a certain age is that I now have the confidence and the wisdom to know which trends to try and which ones to skip. I featured chunky Chelsea boots in my fall trend report, and was super eager to try a pair; yes, I wore combat boots back when they were last popular in the '90s, and normally my rule is that if you wore a trend the first time around, you should pass on it the second (or third, or fourth...) time. I decided to give these Chelsea boots a go, because they're a bit more streamlined than lace-up combat boots, plus they seem very practical for the upcoming winter months, and I wanted to style them in a way that was true to my own sense of style—feminine and sophisticated (I hope) versus the more streetwear-influenced, casual way that Gen Z would wear them. To be totally honest, after seeing these photos, I'm not sure that the boots are "me." But they may be "you," so I thought this was a post worth writing anyway. Here's how I styled my chunky Chelsea boots. 

These See by Chloe boots are super comfortable—there's a ton of room in the toe, the chunky lug sole is thick and padded, and there's a thick panel of elastic at the sides, which allows them to slide on and off pretty easily (often a pain point for slip-on boots). I'm wearing a 39 here, which is usually what I buy in European shoes (I'm almost always an 8.5 in US sizes); I maybe could have gone down to a 38.5, but I have high arches too, and I'm worried they'd be too constricted along the instep. That said, I have room for a thicker sock, which I appreciate in the colder months. These boots come up a bit higher than the ankle height that's been the trend in recent years; I think they might actually look better with pants, or with a shorter skirt, as the covered-leg-to-not-covered-leg ratio here is not totally right. Or maybe this is just such a silhouette shift that I haven't gotten used to it yet. The other issue for me is the clunkiness; I feel like they make my feet look kind of big, and while these boots aren't heavy per se, they're definitely less lightweight than what I'm used to. I'm going to try them again with pants and see if they feel more "me," and if not, that's ok too—at least I tried.

The rest of this outfit is definitely more "me," as these are pieces I've featured before. You last saw this sweater in the rain, and I'm glad Everlane brought it back in slightly modified form. This sweater is definitely on the chunky side, which doesn't always photograph in a flattering way if you're busty like me, but I wear it all the time IRL. It has a slightly cropped length, which works really well with high-waisted pants. I like the contrast of the thick and chunky texture of the sweater with the smoothness of my slip skirt. Like much of Everlane's repertoire, this runs a bit large; I'm in a small, which is pretty generous on me. 

You last saw this Free People slip skirt back in May and it also appears frequently in my OOTDs on Instagram stories—I have it in black and silver, and every time I feature it, several of you buy it (thank you, by the way!). You really can't beat it: it's incredibly flattering, machine washable, and it's under $100. It does, however, run 1-2 sizes small (I went up a size to an 8), unless you have a tiny waist, which I definitely do not. With the combat boots, the slip skirt does lend my outfit a bit of '90s post-grunge minimalism; I do worry that together, the two pieces are reading a bit Goth. Or maybe that's just me projecting my high school insecurities onto this outfit. Either way, the skirt is a keeper. 

And speaking of keepers, I've had this Balenciaga city bag for ages, but I'm glad they're still making a similar version (you last saw it with a tiered dress). This bag definitely elevates the outfit, but its moto-inspired details keep the look feeling cool overall. So while I'm still on the fence about the boots, at least everything else is working—and feels true to my own sense of style. Sometimes it's the piece you've had the longest that really makes it feel the most personal. 

OUTFIT DETAILS: Everlane cardigan | Free People Normani skirt | See by Chloe boots | Balencigaga City bag (current version here)