“What are you wearing?” 01. Every Group Chat’s Favorite Question - Work Edition! What I’m wearing to meetings, WFH zooms, in-office days, and client dinners.

Hi! I am here to kick off a new series (!), which answers every group chat’s favorite question- “what are you wearing?” For today’s newsletter, I thought I would tackle my approach to workwear!

First things first, it would probably be helpful for me to tell you what I do for work and who I’m meeting with. I work on the sales team at a large furniture/home retailer on the commercial side, so my clients are designers who are working on furnishing projects like hotels, restaurants, amenity spaces in residential high rise buildings, etc. I’ve been in sales in this industry since 2012 - first at a custom door hardware company, then a custom furniture showroom at the New York Design Center, then a flooring company where I worked mostly on custom carpet for hotels, and now I’m back to furniture (and a LOT of other stuff haha)!

Anyways! I work mostly from home, but I’m on zoom calls (camera on) daily, so I have to look work appropriate from the neck up :) On days where I have meetings in the city, I dress accordingly. Side note- I live in Jersey City, so I take the train and in about 20 minutes I’m in either downtown or midtown Manhattan, don’t know if I’ve ever said where I live before. Occasionally I go to one of our offices, and that’s its own vibe too. Then- there are client dinners and cocktail/black tie events, like industry award dinners, etc. Whew!

Let’s get into it! And please read my brain dump at the very end - it will make me feel so much better about what I share here!

WFH:

Even though zoom doesn’t capture this, I always wear jeans (no sweats/leggings!). I walk my daughter to school in the morning so I get dressed for that, then stay in the same clothes all day. Not the most exciting category, but I threw together a collage of go-to tops/earrings, in case you’re interested:

Gap sweater + Mejuri earrings (similar here), Gap denim button down + Dorsey earrings, J Crew white button down (size up two sizes on this one, but it’s good!) + gold earrings again, Buck Mason sweatshirt + COS mismatched pearls (different, but very cool, option here), J Crew men’s cotton sweater + Idyl studs + Mejuri ear cuff + Hanes $8 tee (that I used Amex points on, so technically it was free and that makes me weirdly happy)

A few things that help me to not feel blah in WFH clothes:

-I have to take off my socks when I get home from drop off. NOTHING makes me feel more schleppy than jeans and socks. Home bi-weekly pedicures are a must for me as well. Usually OPI Big Apple Red! Lately I’ve been trying to keep a red manicure as well- it feels so special!

-Lip color! I love this one and it lasts a long time. Another recent purchase was this lipliner, recommended by Cate Holstein, founder of Khaite, in this article.

-Jewelry that never comes off. I wear three rings 24/7 365 (wedding band, and two symbolizing each of my kids). I am planning on getting zapped soon as well!

OK, now before I share the next categories, I want to speak about my approach for a second. I LOVE outfit repeating. You know the variables and you know you will feel confident and comfortable. In this spirit, I try to have THREE go-to outfits for both F/W and S/S for each category of the below. Back in 2023, I decided to focus on rebuilding my work wardrobe after years of relying almost exclusively on Rent the Runway. I chose black pants as the first item I needed to nail down, and then I planned to fill out the categories from there, making sure everything could tie back to the initial pair of pants. Two years later, it’s still a work in progress! The fact that I work from home helps a lot, but I still do need these outfits multiple times a month. From doing this exercise, I’m happy (proud?) to say that from 19 items of clothing and 4 pairs of shoes, I can make outfits with enough variety to not get sick of wearing them. That being said, if I were starting over now, I would follow Irene Kim’s How To Build A Foundational Wardrobe series as my bible.

My items for this exercise break down like this:

Meetings:

The building block of my workwear wardrobe, and my singular favorite item of clothing, are these black pants from Toteme (I bought them secondhand on TRR). I love the interesting curved leg shape, the built in waist detail, and the slight nubby texture they bring to the table. I paid $170 for them two years ago, and have worn them SO frequently, I’m sure the cost per wear is around $2. Paired with them is an old black blazer from Mango, a (very) old bodysuit from Zara, and new boots from Matisse (they sadly sold out in this color). My leg looks photoshopped or something hahah- the fabric did something odd in this pose!

A black wrap dress is a great basic that can be layered under jackets in winter, and worn on its own in summer. I bought this one in 2019 from Everlane and I’ve worn it a thousand times since. I like to wear it with this blazer (an old Mango find) with the sleeves sort of scrunched up. You can turn your blazer inside out and use a big safety pin on the arm to keep them scrunched, BTW! These boots are also Matisse, and so comfortable and well made. I feel very “professional” when I wear these. My watch is from March Hare and I never shut up about it, lol. You can easily swap the band out, and I own three now, so call me a collector!

I bought this Marni dress via TRR for $130 in 2023, and I wasn’t sure if I liked it. Then one day I randomly tried layering it over this sheer shirt (old from Dissh), and I like it styled this way! I love the huge pocket on one side only. It’s also just incredibly well made and the fabric is so heavy and hangs well. These boots are five years old, Seychelles brand from Nordstrom. They’ve held up well, and although the silhouette isn’t the most “fashion forward” shape in 2025, I’m ok with that. They are good quality and they get the job done.

In Office:

My beloved Ayla jeans! I think jeans are acceptable in a lot of different office environments in 2025- especially when dressed up with a blazer and a dressier shoe. This shirt is a nice cotton poplin (bought via TRR, brand is Finley) and the blazer is the same old Mango one from above.

This is actually what I wore on my first day at the office at my current job! Same pants as above, an old COS knit tank (it’s a heavy knit- I can’t find anything similar on their site now, sadly), my very very very old Theory jacket, and Matisse boots. No notes- great office outfit!

This skirt (old COS) might be too short for some office environments? I don’t think so, but this is an easy go-to for me. The shirt is an excellent laying thing from Everlane (noticing a theme?), same blazer and boots as above!

Client Dinners:

Pants again, and you can finally see the waist detail in this pic. Along with my black blazer, these appear in all three categories, really proving their importance. The top is a bodysuit from Everlane (on sale for $23!), the shacket is old Club Monaco - fancier when worn over your shoulders! - and the shoes are old Ayede (pricy for my typical shoe budget, but they are my only pair of pumps and I LOVE them). I wore this outfit to dinner with clients at El Nico recently - definitely worth it for the bathroom lighting experience alone:

I posted about this outfit in Notes recently, where I mentioned that I repeat this outfit often, and I mean it! I feel comfortable and chic and the individual pieces can be used to create a lot of other outfits as well. The sheer top is the same one I layered under the Marni dress earlier, the vest is old from Everlane, the skirt is from J Crew, and the belt is from Sezane. All very approachable price points, but IMO it reads as being much more expensive all layered together.

This outfit is more casual, but I wore this to a client happy hour last week. BTW if you ever need a great HH spot by Grand Central, Albert’s is it!! Jeans are the Miro from CoH, and top is an old linen t shirt from Banana Republic. Everything else was worn in outfits above :)

So there you have it!! To keep things fresh, I would love to add a few items - a snakeskin belt for jeans, or to wrap around the waist of a jacket, a navy blazer, and still really wanting these green leverback earrings:

And now for that brain dump - I hope this doesn’t sound defensive, it’s actually just my insecurities getting to me! I think it goes without being said that I am not a stylist, or a fashion expert, or even in that industry, and I consider myself a student, not a teacher. I am soaking up everything I can learn from the amazing stylists and fashion industry experts who write for Substack, share on Instagram, etc., and then - I try to apply what I’ve learned. I LOVE writing this newsletter and sharing my trials and tribulations, and getting dressed is so fun for me (I consider it my “hobby”) so it’s also really fun to share and write about it. And I love interacting with the amazing people who are drawn to this personal style niche on Substack. There is a part of me that looks at the above outfits, and begins to critique them, or question if they’re “share worthy,” but you know what - I’m going to turn the other cheek and keep doing this! It’s fun! And it’s low stakes! Long story short, I just want to write this as a disclaimer that I’m not trying to come across as “knowing what I’m talking about” - this is just a real time airing of experiences. It’s challenging to figure out personal style, what silhouettes you like for your own body, and what makes you feel like a million bucks, all while sticking to a budget. It’s also not even realistic that you WILL always feel like a million bucks. I like knowing that other people can see me being challenged, and maybe feel less alone in that.

I re-wrote my bio here the other day, which is a small thing but can not be discounted! Summing up what you are trying to get across in one sentence is HARD. In fact, my Just For Fun title is stolen from the Just For Fun category they offer on Instagram. I had “artist” as my category for years and it always felt heavy to me (silly, I know) so I changed it one day to JFF and man did I feel liberated! So anyways, I changed my bio to say: “Just a mom of two, standing in front of a full length mirror, asking you to talk about clothes with her” and I think that pretty well sums it up! TLDR: I am not an expert and I’m not asserting myself as one, and I really hope that sentiment is coming across without me saying it… but I’m saying it just in case ;)

Ok, thank you from the bottom of my heart for indulging me! I’ll be back in two weeks for another installment of “A Week of Outfits”!

Talk soon :)

Emily

P.S. One thing I didn’t touch on are trade shows, but I have one coming up soon and I’ll try to post pics to notes! Trade show dressing is fun, and typically I do Rent the Runway for that!