I’m doing a new thing today: I’m styling an article of clothing three ways with some of my favorite wardrobe staples. It’s certainly not a revolutionary concept 😂, but let me know if this is something you’d like to see more of!

Since J.Crew Factory is one of my absolute favorite brands for the classics, we’re teaming up for this first post to specifically feature office-appropriate outfits that are both easy and comfortable. I’m still scarred from owning horrible workwear during my stint in journalism, and I’m only now realizing how much of a negative impact that it likely had on my performance! Work is hard enough; there’s no reason to be uncomfortable. And if you love your everyday attire, you’ll likely be happier and more motivated at the office. :)

Btw: Factory is having a huge sale right now, so this is a great time to stock up on wear-to-work essentials. Now until March 5th, you can take 50 percent off site-wide, and an extra 40 percent off clearance with code “SOEXTRA.” (which makes for some insane prices! In stores, you can take the 50 percent off, too. No code needed for that, haha.)

Okay! Today’s article of choice? The High-Rise Girlfriend Chino Pants from J.Crew Factory!

For the longest time, I associated everything khaki with my Catholic school days… and therefore shied away from it. Recently, though, I’ve been seeing (high-rise) chinos make a comeback, and I’m loving it. Of course, I’m not styling them with polo shirts embroidered with school crests on them anymore. 😉 But today I’m sharing three ways I am wearing my high-rise khakis!

High-Rise Khaki Pants styled 3 ways
High-Rise Khaki Pants styled 3 ways
High-Rise Khaki Pants styled 3 ways
High-Rise Khaki Pants styled 3 ways

With a statement cardigan

High-Rise Girlfriend Chino Pants (Go one size down.) / Leopard Open Cardigan (TTS.) / Drapey Machine-Washable Top (TTS. This dotted version is adorable, too.) / Captoe Pumps (Captoe Flats here, which I also own and love! Both are TTS.) / Reversible Tote

High-Rise Girlfriend Chino Pants: These are the BEST. Go one size down, as they definitely run large. But they’re wonderfully soft and comfortable–even when sitting for long periods of time. (I feel like that’s the ultimate test, haha. No wedgies!) The high-rise cut is also extremely flattering, so if this is your first time moving away from skinny pants, this is the perfect transitional pant. Another plus is that the pants have pockets that don’t stick out and widen your hips. For a more casual look, you can also roll them and pair them with sneakers! (I love the look of a striped t-shirt, too. This one’s cute, too!)

Style tip: Tuck your tops and sweaters into the pants, as this helps you achieve a polished legs-for-days look!

Leopard Open Cardigan: This long cardigan is gorgeous. It’s so well-made that I can’t believe its price! The longer length really elevates outfits, and the leopard print gives them that something extra. I remember hardcore struggling with air conditioning when I worked in offices, but this sweater prevents frostbite while also making you look super cute and fashionable. Highly recommend. (TTS.)

Drapey Machine-Washable Top: I’m so over silk. It’s too difficult to maintain, and I don’t have the time or the patience. Whenever Factory comes out with a new batch of poly tops, though, I almost always add another to my collection because they look just like silk yet are machine-washable and rarely need steaming or ironing. I have this top in both black and white, and I’m constantly reaching for it. It tucks perfectly into pants and skirts, and it can be worn from day to night with both nicer bottoms and jeans. Winner for sure! (TTS. This dotted version is adorable, too.)

Captoe Pumps: Stop the presses. Factory carries captoe pumps and flats that look like a million bucks yet are actually amazingly affordable. I toss these heels into my tote all the time when I’m out and about in the city, that way I can change into them for events, meetings and restaurants. TTS for both.

High-Rise Khaki Pants styled 3 ways

With a drapey top

High-Rise Girlfriend Chino Pants (Go one size down.) / Drapey Machine-Washable Top (TTS. This dotted version is adorable, too.) / Captoe Pumps (Captoe Flats here, which I also own and love! Both are TTS.) / Reversible Tote

This is a good example of how the top can be worn on its own, too. I love khakis paired with a black shirt or black sweater because it adds contrast and dimension. And seriously: whenever you’re wearing a black top and a pair of pumps, you look dressy. Heck, I’ve seen black tops, pumps and joggers done exceptionally well!

Other black top options ^

Reversible Tote: Definitely need to chat about this bag, too. It’s fantastic for work, as you can carrying it in the camel or black color–what more could you need?–and it fits a ton, including my 15-inch laptop. It’s also soft and therefore comfortable to have on your shoulder. (I’m telling you: Nine times out of 10, I find faux leather totes to be nicer!) You can’t beat the price point, either.

High-Rise Khaki Pants styled 3 ways
High-Rise Khaki Pants styled 3 ways
High-Rise Girlfriend Chino Pants
High-Rise Girlfriend Chino Pants
Softest Chambray Shirt
Softest Chambray Shirt

With a chambray shirt

Softest Chambray Shirt (Runs a bit large. Here’s the popover version.) / High-Rise Girlfriend Chino Pants (Go one size down.) / Captoe Pumps (Captoe Flats here, which I also own and love! Both are TTS.) / Reversible Tote

I’m going to try to not sound like a lunatic right now, but YOU NEED THIS CHAMBRAY SHIRT. It’s incredible. I’ve tried a lot of chambray shirts over the years–including pricey designer ones–and this one is by far the softest (and therefore coziest) I’ve found. Huge fan. Love this shirt and I hope you welcome it into your home, too, haha.

Chambray shirts and tops are some of the most versatile pieces you can have in your closet. They pair well with jeans (favorite pair of Factory jeans, btw), white jeans (these are so soft), khaki pants, dress pants, dresses and shorts. I’m going to go ahead and advise you to forget about that chambray-and-tulle-skirt trend, but besides that, chambray goes with just about everything. (Which makes it a great choice for travel, too!)

My favorite one runs a bit on the larger side, so I size down in it. In the above photos, I’m wearing a size XS, and as you can see, it’s still plenty roomy. And here’s the popover version in case you’re interested!

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Let me know if you’d like to see anything in particular for my next “styled three ways” feature. :)

This post is sponsored by J.Crew Factory; all opinions are my own. As always, thank you so much for supporting the partnerships that keep Kelly in the City up and running!