Style Day: Wearing Cropped Pants in Winter

Cafe Capris from J.Crew are my all time favorite work pant. I know many gals like the Minnie, but the cut and fabric do not work well for this pear shaped gal. The Cafe Capri was perfect for me, until we had this unseasonably cold winter here in the south. And it looks like we’re not quite done with cold weather yet! Wearing the cropped pants with bear ankles in 30-40° weather wasn’t working out. I started testing silhouettes with warmer shoe options over the past few months, so this post has been a long time in the works! These are all outfits I’ve worn before and in the temperatures I recommend them with, so they work for me. I run a little hot, so adjust your picks for your normal body temperature.

Ideas for wearing cropped pants in winter weather ~

After doing this, I have a whole new appreciation for outfit and fashion bloggers, especially those that take their own pictures. You are now among the ranks of heroes for me. This was hard, to say the least.

55°+: the flats

Ideas for wearing cropped pants in winter weather ~ www.hayesdays.comIdeas for wearing cropped pants in winter weather ~

Arguably the best looking shoe with cafe capris. The issue I run into with flats with my body shape is keeping the bottom half balanced out with the top half visually. I chose a light weight top and a cardigan over it, so it doesn’t look overly heavy on top. Maybe it’s just my eyes, but I think that the patterned flats also play a visual trick in this balancing act. Most of the time, a variation of this outfit is what I’m wearing to work.

50°+: the heels

Ideas for wearing cropped pants in winter weather ~ www.hayesdays.comIdeas for wearing cropped pants in winter weather ~

Wedge, kitten, or stiletto, I’ve been able to wear heels in weather slightly cooler than flats because footies work better for me in heels rather than flats. These shoe options may swap for you if footies work better for you in flats. These are my footies:

Ideas for wearing cropped pants in winter weather ~

I got them at TJMaxx/Marshalls. They always have a wide selection. They’re padded, warm, have grippies in the toe and heel to keep them in place, and work much better with heels for me, and I’m mad I can’t remember the brand. Check out your options here. They’re also called slipper socks and toe socks. I haven’t found a pair that works well with flats yet. (If you have let me know! It would make my flats outfits much warmer!) Also, heels make your legs look longer, so you can go a little bulkier with your top half by adding more layers. I chose a 3/4 sleeve light weight sweater (a Tippi to be exact) and a medium weight jacket that can be removed if your work environment is warmer or put on if it’s cooler.

45°+: the bootie

Ideas for wearing cropped pants in winter weather ~ www.hayesdays.comIdeas for wearing cropped pants in winter weather ~

Now we’re getting warmer, especially if it’s not windy! This is not a look I naturally go for. It’s a little heavier looking than what I usually wear, but it’s warm and this has easily become my favorite combination. These booties, in particular, make my feet look visually heavy, but the short shaft hides socks. I can wear thick workout or even short wool socks from sporting goods stores and keep my feet REALLY warm with these booties. (No more bare feet shots of my socks. You’re welcome.) This particular style bootie limits my tops to a more casual look. Thankfully, this outfit is appropriate for my office. I have yet to find a bootie with this length shaft that looks dressy.

45°-: the riding boot

Ideas for wearing cropped pants in winter weather ~ www.hayesdays.comIdeas for wearing cropped pants in winter weather ~

The riding boot is the most polished boot option that I feel works well with the Cafe Capri. I’ve also done Western style boots with my Cafe Capris, but I can’t get a work appropriate combination with those boots. The riding boot covers up any ankle. It’s best for windy days. I wear tall trouser socks and tuck my pants into them so they don’t bunch up in the boot when I’m walking. This pair makes my legs look a little longer than other pairs I’ve tried, due to the fact that they are knee high, so I feel like I can layer more on top. I’ve done this particular outfit (plus gloves, hat, and heavy wool coat) in 35° weather and it works for peeling off layers in the warmer office and still being comfortable. While this may not be office appropriate for your work environment, this is the warmest option. I think your best bet if the weather is this cold and you still need to be office appropriate is to put on heels when you get there.

For the past two months, I’ve been putting together variations of these outfits. How have you been transitioning your Cafe Capris into cooler temperatures? Have you found booties and boots that are better for your work?

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  1. For me, I have such long legs that capris would look super short. PLUS, I live in a place that the weather has been well below your temperatures (today is reading 4 degrees. Four.) I love flats, haven't done the booties thing because I feel like I'm not stylish enough for them. Tall boots get me through the fall & winter. 🙂

  2. I skipped the booties for several years, but I felt that this pair was toned down enough for me to try and I really love them. With skinny jeans (or jeans in general) there's no gap, and it's nice to not have to fool with anything knee high. Just find a plain pair and give them a shot. These are Jessica Simpson. I don't remember the style name though. Yeah… at 4° I'm pretty sure none of this would work. The riding boots outfit I've worn in 28° weather, but that's it. There would be several pairs of leggings and layers involved in 4°. lol!

  3. Well, yes. I basically wear colored jeggings and tall boots to work every. single. day. And then skinny jeans when I'm not at work. 🙂

  4. My ankles hate me in the winter, such cute options for stying thse here in the midst of the cold temps.

  5. I think boots and booties are the perfect way to wear capris during the winter (and for those under 45 degree days) I have to try these pants now. They look amazing on you!

  6. Thank you Ashley! They're great pants. There is a dark blue on super clearance at J.Crew online today. It's a seasonless blue too. I recommend them even more at 40% off $40 and free shipping!

  7. Thanks Ginny! It means a lot for you to say that. I think you do a fantastic job with your blog and photographs.