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Four Ways: Styling Ideas for Leggings

Mar 17, 2020

I swore that I would never write the post about styling leggings “for work.”  And under normal circumstances, I wouldn’t.  But with so many of us working remotely, and all of us in need of as much comfort as possible, these are not normal circumstances.  This is work fashion in the time of coronavirus.

Last Friday, I wrote about the mistakes I made when I was first working from home.  In the post, I talked about the importance of continuing to dress for work, and some of you thought I meant wearing suits or traditional office attire even at home.  But even I cringe at the thought of wearing full work attire at home, unless I have a client meeting or virtual interview, because it sounds so uncomfortable (and hard on the dry cleaning bill).

Instead, I wanted to caution against falling into the pajamas all-day or sweatpants every day trap.  Once in a blue moon is fine, and it happens to everyone.  We all have days where we just can’t do it.  But after a couple of days, dressing too casually can damage the work mindset that is so essential to maintaining productivity and focus when you work from home.

Instead, wear ponte work trousers, jeans, or leggings.  All are good options.  But let your wardrobe contribute to your work mindset by putting together outfits that are casual and comfortable, but also styled and pulled together.  Because when you look good, you feel good, and that is so beneficial to your work.

So let’s get real about what we’re all going to be wearing this week, and style the black leggings we all own in a way that is comfortable, comforting, and pulled together.

One. Cuyana Recycled Cashmere Cardi // J.Crew Scoopneck Tee // Superga Leopard Sneaker // Baublebar Huggie Hoops

Two. Rebecca Taylor Poplin Tunic // Mural Oversized Blazer // Rothy’s Honeycomb Points // Gorjana Onyx Studs

Three. Land’s End Stripe Tee // J.Crew Regent Blazer // Veja SDU Sneaker // Sterling Forever Necklace

Four. Ottoman Slouchy Tunic // BP. Velvet Hoops // Gucci Rouge Lipstick //  Ugg Slippers 

One. This incredibly cozy outfit is still incredibly chic.  The soft neutrals, the fabulous sweater, and the pop of leopard make this outfit perfectly styled, but also perfectly relaxed.   And from the neck up on a video call, it just looks like you’re wearing a great sweater.

This sweater from Cuyana is such an indulgent gift to yourself, but you will not regret it.  And using recycled cashmere is just such a great idea.  Also in black and grey.  Need something more affordable?  This Boohoo wrap (also in plus) has a similar look.  But if cost is your concern, I think this Goodnight Macaroon draped cardigan has a much more sophisticated feel than the wrap.

I own these Superga leopard sneakers in the bigger print, and the material is really soft, so with a cotton no-show sock, they feel like slippers.  And the earrings are such a cool, pretty accent with the slim huggie style.

Two. Need to look like a lawyer, but don’t want to go full suit?  Much like a TV anchor, no one needs to know what you’re wearing on bottom.   So this outfit is leggings on the bottom and professional attire on top.

I chose a longer tunic blouse because I prefer a longer top with leggings.  For something more affordable, this Calvin Klein non-iron shirt is great. Plus-size?  Try this AndComfort tunic.

Um, how great is this blazer?  It’s a gorgeous, unique color with the smoky pale blue.  It’s a cool shape.  And it’s $75.  You can buy it to work from home and still wear it over a black sheath dress when this is over.  Add to cart.

Sold out in your size?  Try this Modcloth teal blazer and this dusty blue Vince Camuto blazer also have blazers in cool blue hues.  And Mural has a cool, relaxed trench in a seafoam hue.

I added these black onyx studs because onyx is supposed to help the wearer with the ability to conquer fear and maintain stability. I’m not usually a believer in such things, but in these times, what can it hurt?  Even the placebo effect is still an effect.  Plus, they’re pretty and versatile.

Three. Land’s End tees are some of the best.  They’re soft and well-made, and they’re so inexpensive.  Almost all of the tees are under-$25, and if you wash them in cold water and hang to dry, they last forever.

This striped tee pairs well with my favorite J.Crew Regent Blazer.  The jacket has such a cool, pulled-together vibe.  In camel, in navy, in black, you can’t go wrong.  Also in plus-size and petite.

These sneakers have a great vibe to them.  The black sneakers are a bit dressier (if that’s the right word when talking about sneakers) than the white.  And they blend a bit better, so it’s not like, “Pow! Look at my sneakers!”

Prefer a flat?  Give these Everlane Day Glove flats a try.  My friend Meghan is a huge fan of Everlane’s shoes, and she lives in Brooklyn, so she knows a good walking flat.

Four. It’s back! If you missed out on Free People’s Ottoman Tunic Sweater it is finally, finally restocked in the colors and sizes you’re looking for.  And since it’s not a wool sweater, and has an oversize shape, it’s not a really warm sweater.  So on these 40-degree days in March and early April you can wear it, and then store it  away for the fall.

I designed this outfit for a wine-night happy hour with friends held virtually.  So many of us our using FaceTime or Google Hangouts to spend time with friends while we socially distance, that I felt like there should be an outfit for that.

This look combines the chic, oversized sweater with a fun, affordable statement earring and slippers.  Damn right.  Because wine night at home means comfortable feet.  And just for fun, add a gorgeous red lipstick like this Gucci lipstick that I am seeing on so many Instastories.  Or for an affordable choice, Revlon’s Super Lustrous lipstick has a lot of great reds.

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Career Style, Style

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  1. TheLOOP says:

    The first and fourth outfits are perfect. But I can’t bring myself to wear any footwear except plush socks or house slippers when I am working from home.

  2. Meghan says:

    Thank you for the shoutout! They are indeed SO comfy! Love the styling you chose in this post!

  3. sara says:

    That light blue blazer for look 2 is a dream! Love all of these.

  4. Monica T says:

    Oh I wish I had the pieces for one and three right.NOW. Thank you so much for these posts! As someone who has never worked from home on a regular basis, and only begrudgingly on occasion (IT work REQUIRES 2 big monitors for REAL) this shelter in place thing is a rough adjustment. We’re all just making it one day at a time right now, so thank you for keeping up the great content and helping the rest of us feel normal, even if it’s just for a minute.

  5. Susan says:

    Can I make a weird fashion prediction ? By the time this whole pandemic is over, we are going to be so TIRED of athleisure and the casual nature of our society that we are going to start dressing up to go out like we used to in the old days. Crazy? A fever dream? Maybe. But I hope so.

    • kelly says:

      I like your prediction! I’m super interested in seeing where the trends go after all this. I was waiting/watching for some things to swing around (like what comes after the sometimes terrible experience of dating through apps), but after this all of this the trends are probably going to go in ways no one sees coming.

    • Belle says:

      I am here for this fever dream.

    • Joanna says:

      wow, I like this idea as I enjoy dressing up.

  6. Jord says:

    Maybe I missed it, could you include the link for the leggings?

  7. Joanna says:

    Love love this. Please keep this content coming. I am rotating all of “comfy” types of pants while working remotely.

    • CLSDC says:

      Yes, and also what we can wear to feel put together when we’re working and also trying to educate our children. This is real-life nightmare – working full time, taking care of little ones, and I can’t seem to get out of my PJs or workout clothes. But if I wore that cashmere sweater (although I’m in LOOOOVE), or the blue blazer, I’d end up with playdoh, markers and yogurt tube smears all over them as I’m rushing between my computer and wherever the children are attempting to “learn” but in reality just killing time. Is there an outfit for THAT situation, as I really need one and my daily ritual sweatshirt is in the wash…

      • Heather says:

        I’m doing black (not faded) skinny jeans, black or white tee, with a hoody and swapping out with a camel or black blazer when I jump on a call.

  8. Jess says:

    Wore a riff on outfit one today, and got called out on an all agency video call for looking put together! Wouldn’t mind a few more of these to keep on the back burner for the next few weeks (or months).

  9. Rachel says:

    the fly in my ointment is the baby and preschooler….otherwise I would love to dress up more. But even working I am crawled all over, carrying a baby, etc…its a wonder I have managed to get anything done!!!!!

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