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Two pairs of SUPER comfy work pants, and 8 ways to style them!

Oct 28, 2021

Hellooo and happy Thursday! (It is Thursday right?)

Putting the finishing touches on this post from the coffee shop! Had another LONG night with June last night so I am in need of all the caffeine. She has learned how to roll over onto her tummy and prefers to sleep that way, but then can’t get herself BACK over if she decides she’s no longer comfortable. Thus, squawking multiple times a night. I’m excited though because I have plans to get together with my best friend Kate tonight so that’s helping me power through! Maybe I can even sneak in a nap before I pick June up from daycare.

Anyway, I know many of you will be excited for today’s post, because it’s been a highly requested topic!

Whenever I ask what fashion-related topics you need help with, the resounding answer lately is, “HELP! What do I wear now that I’m back at the office!? I can’t go back to uncomfortable work clothes! WHAT ARE PANTS?!” 

So THAT, my friends, is what we’ll be talking about today! I had a couple readers recommend LOFT to me for really comfortable but stylish pants that LOOK like “real pants” but are in fact stretchy and super soft and comfortable.

I ordered two pairs to try out and they fit the bill exactly–I know you’re going to love them too! Even if you don’t go into an office, I think they’re still a cute, stylish staple to have in your wardrobe for whenever you do need to look a bit more polished and professional!

Two pairs of SUPER comfy work pants, and 8 ways to style them!

First, let’s discuss the pants.

PSA: They’re also 40% off today with code FALLFUN! 

LOFT flannel pull-on tapered pants: (On sale for $48!) 

These look like more of your traditional “work” pant, but they’re SUPER soft flannel and have an elastic waistband in the back (but also have belt loops if you want to dress them up with a belt!) You could easily make these business professional if you needed to with a pair of pumps, blazer, and a crisp button down, but I went with three business casual stylings here to show their versatility a bit more!

Sizing: These run TTS. I took my normal size, which is small. I am 5’6 for height reference and you can see where they hit me just above my ankle.

LOFT pull-on knit wide leg pants: (On sale for $48!) 

Come in both olive and grey. These are legitimate SWEATER pants. Incredible. But they look like real pants! (Where the hell were these in 2020!?) This pair is arguably a bit more casual but perhaps even more versatile–I love that they can be dressed up to look professional but I wear them around the house like sweatpants–with sneakers and a sweatshirt, etc. Basically sweats that aren’t sweats, and comfy pants that aren’t athleisure. Because let’s be honest I don’t ALWAYS want to be wearing athleisure. Sometimes I want to look chic without putting in the effort to do so.

Anyway, we aren’t talking about casual outfits today, we’re talking about work-appropriate outfits, so I won’t be styling these pants super casually, but you can use your imagination as to what they’d look like with sneakers! (CUTE!)

Sizing: I took my normal size in these (small) but they’re a little bit loose. I don’t know that I would go down to XS though as I don’t want anything tight on my waist these days. I would say if you’re usually one of two sizes, go with the smaller one, but otherwise your normal size should be good.

How to style the LOFT pull-on tapered pants 4 ways:

Let’s jump into how to style each pair! I also just noticed that almost every top I’m wearing here is Sezane. Probably because their items are the only clothes I’ve purchased recently! I’m obsessed. LOL. Anyhow. Carry on!

LOFT pull-on tapered pants

Pants: LOFT (Run TTS, wearing small) Sweater: Sezane Gaspard Sweater (I took my normal size but it’s a bit slouchy, size down if you want it a bit more formfitting. Also, it’s reversible!) Shoes: Rothy’s (use code JESSK20 for $20 off your first purchase of $100 or more! I went with my regular size but reviews say to size up if you’re in between.) Scarf: Hermes (don’t see this particular one online!) but Amazon sells a really cute budget version!

I love this combination–I think it looks so lovely with all the neutrals together, and the pants bring a pop of color! Every piece I’m wearing here is super versatile and can be dressed up and down/mixed or matched! A very solid combination to wear into the office or anywhere, really!

LOFT pull-on comfy work pants

Pants: LOFT (Run TTS, wearing small) Sweater: Sezane Lison jumper (Runs big/oversized. I got a small but could’ve gone down a size, but I like how slouchy it is! FYI–I’m wearing it with the buttons in the back! It’s reversible. This version is a pullover and very similar as well!) Headband: Similar here Boots: Eliza Boots c/o ABLE (Use code JESSKEYS20 for 20% off! Run TTS! Talked more about them here!)

More common questions I get this time of year?

“How do I wear straight leg pants with ankle boots” and “How do I keep my ankles warm?!”

I thought I would address both of these with this outfit! It’s a formula you can use with any pair of straight leg pants and any pair of booties. I do think booties with a pointier toe and/or a slight heel are easier to style with this cut of pants because a pair of flat boots can look frumpy depending on the combination. (Not always, of course, but the former are easier to style). I like there to be a little it of room in between a pair of straight leg pants and the top of the ankle boot.

Otherwise, it looks like you just have rectangle legs because it’s hard to discern where the pants end and the ankle begins, know what I mean? (I know that’s not always the way Gen Z styles them but I’m not a Gen Z.)

Worried about cold ankles? Wear socks!

Just make sure they match the color scheme of your outfit. (And keep to the same color scheme as your boots–so if you’re wearing tan boots, go with tan socks. If you’re wearing black boots, black socks). If the combo isn’t feeling quite right to you, try wearing the same color top as your boots. (So for example, if I were wearing black boots and black socks with the outfit above, I could swap for a black sweater and the outfit would feel more streamlined/cohesive!) Sometimes too much color-blocking can feel thrown together.

I recommend stocking up on several pairs of socks that are a range of shades from beige to oat to greys to blues to blacks so you always have the right color to go with your outfit. (No need to spend a lot of money, something like this multipack from Amazon will do the trick!) You want to make sure they aren’t super chunky too–you don’t want to add bulk!

How to style comfy work pants

Pants: LOFT (Run TTS, wearing small) Blouse: Sezane (runs TTS) Gold Ankle boots: Sezane (run TTS)

I got these gold booties on our Sezane shopping trip in Paris. They are SO outside what I would typically buy, but to me these are the winter version of my gold Loeffler Randall sandals! Gold is also a neutral and these boots just make ANY simple outfit so fun and snazzy! If gold isn’t your thing though, they come in normal colors, too! I love the shape of the boots and while I haven’t worn them a ton yet, they are quite comfortable so far! I think this is a great way to jazz up a work outfit with just a change in footwear!

LOFT tapered pants

Pants: LOFT (Run TTS, wearing small) Blouse: Sezane (runs TTS) Shoes: Rothy’s (use code JESSK20 for $20 off your first purchase of $100 or more! I went up a half size.)

Same outfit, but another way to jazz up your outfit with footwear! I love a red ballet flat–adds so much flair to your outfit while still remaining polished and professional!

How to style the LOFT pull-on knit wide leg pants 4 ways:

LOFT pull-on knit wide leg pants

Pants: LOFT (Run TTS if not SIGHTLY big. Wearing small) Top: Sezane (TTS, boxy fit. See how I styled it in Paris here!) Sweater blazer: Mine is the J.Crew Sophie blazer which they have discontinued and they’ve replaced it with the new iteration: The Eloise sweater blazer. Also super cute and versatile!

I call this look “polished casual.” Still professional for a work setting, but everything here is ultra-soft and feels like pajamas! (Sweater blazers with sweater pants for the win!) It’s no secret that stripes are my favorite pattern, especially in the fall and winter, because they go a long way to make an outfit full of layers a lot more interesting!

LOFT wide leg pants

Pants: LOFT (Run TTS if not SIGHTLY big. Wearing small) Turtleneck: J.Crew (Run TTS, I take a small) Madewell also makes a similar version! Loafers: Gucci (I ordered a size down from my US size. I’m a US 8 and took an EU 37.5, however, based on the reviews on the website, they all say TTS, so maybe they changed the sizing!) I also love the Sam Edelman loafers for a more wallet-friendly alternative!  Cardigan: Super old but similar here! I’d also recommend this longline cardigan from ABLE (Use code JESSKEYS20 for 20% off at ABLE! I have it on grey but it comes in a similar camel/oat color as mine above)–it’s so versatile you can button it up and wear it as a dress too!)

Shocker! More stripes!

Here’s an example of how I have (and will continue to) wear these pants when working from home or from a coffee shop! They’re a match made I heaven for a longline cardigan! You could also easily swap the loafers for some cute white sneakers for a more casual look that would be perfect for the weekend or for travel!

LOFT Office outfit ideas

Pants: LOFT (Run TTS if not SIGHTLY big. Wearing small) Blazer: Old Everlane (similar here!) Madewell also has quite a few cute ones as does J.CrewSilk button down: Everlane (my exact one is years old but this one is their latest iteration!)

A boyfriend blazer is such a great wardrobe staple that I have loved for many years! Chances are, if you have one, it’s been collecting dust–but now you can drag it back out! I love an oversized blazer because I think it’s a bit more easy to style for going out, but is also great for work! (Layer a slinky camisole like Sezane’s Paloma top for a date night!) It pairs beautifully with these comfy pants to polish them up a bit! You can also add a pair of pumps if you need it to be a bit dressier.

LOFT Office pants

Pants: LOFT (Run TTS if not SIGHTLY big. Wearing small) Silk button down: Everlane (my exact one is years old but this one is their latest iteration!) Shoes: Rothy’s (use code JESSK20 for $20 off your first purchase of $100 or more! I went with my regular size but reviews say to size up if you’re in between.)

If an oversized blazer isn’t exactly your style, look how much different this outfit looks with the the blazer removed! Voila–you have a beautifully simple but chic Parisian-inspired outfit. (This would also look so pretty with a trench over the top! This is the one I’ve owned and loved for years! Burberry vibes for $100!)

That’s all for now! I hope this was helpful. If these pants are what you’ve been looking for, make sure to snag them before the 40% off sale is over!

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