Above board

What to wear when you're circling back on that email

If at this age you aren’t meant to live an uncomfortable life, keep on scrolling. However, if you are among the many of us who must earn a living (and who take the subway and not Lorazepam daily), you may be panicking about a return to office after a summer of spritzes and 8 consecutive Fridays tethered to your phone’s hotspot at Indian Wells Beach so that you appear available in case anyone asks.

Aside from personal styling I have been in the professional workforce for 14+ years, spanning investment banking to venture-backed startups, and now at Instagram. We spend so much of our adult lives at work yet underemphasize the importance of investing in pieces that will last for years.

While I occasionally recommend fast fashion dopamine hits, my clients don’t work with me for the cheap thrills. Instead, I encourage quality over quantity (one of the many reasons I love shopping on TheRealReal), and workwear is no different - your job may be boring but your wardrobe doesn’t have to be uninspired (there is no ambition killer quite like a closet full of Ann Taylor).

The fun thing about all of the outfits below is that no individual item reads ‘work’ and you won’t have the same visceral reaction to wearing them on the weekends as I did looking at my pregnancy pants after giving birth. Incorporating knitwear, layers, accessories, and different proportions gives us more range than we realize.

So while I can’t save you from your passive aggressive Slack messages, I can help you dress with the confidence to send them. Please enjoy these collages paired with my favorite euphemisms that are NSFW.

1. Great for pretending you’re pumped to take clients to dinner at the Midtown location of a chain restaurant owned by a private equity firm

Bone Cuff Bracelet | My new favorite bodysuit - trust me | Olive Taffeta Drawstring Pants | Shearling Tote | Western Slingbacks | Vintage Tassel Necklace | Burgundy Mary Janes (so comfortable) | Black Turtleneck Bodysuit | Cream & Black Silk Skirt

2. Thank you for only responding to the least urgent part of my email

Collar Necklace | Cotton Drawstring Pants (machine washable!) | Cream Pumps | Blue Sweater | Red Scarf Sweater | Calf Hair Flats | A really good crepe pant with a drawstring | Striped Tote

3. Like I always say, every day at work is another day closer to retirement

Earthy Bangles | Green Silk Scarf | Pleated Mandarin Collar Jacket | Brown Suede Tote (One of the best investments I’ve ever made - so highly functional and amazing quality, also great for travel) | Fringe Poncho | Leather Pendant Necklace | Long Sleeve Tee (the bell sleeves make this dressier & more flattering | Black Poplin Skirt (another absolute favorite workhorse piece) | Burgundy Patent Slingbacks

4. I hope this email finds you well dressed or not at all

Green Suede Tote | Leopard Flats | Not your grandma’s pearls | Blue Dress | Brown Jersey Kimono Top | Cream Pants | Brown Snakeskin Heels (extremely comfortable) | Navy Peplum Top | Printed Scarf

5. This outfit earns a ‘greatly exceeds expectations’ on its performance review

My favorite t-shirt for layering or on its own | Tan Slingbacks | Silver and Black Collar Necklace | Horizontal Stripe Top (I just bought this) | Pinstripe Pants | Gray Melange Top | Navy Drawstring Shorts (yes shorts can be corporate!) | Pierced Heels | Green Tote | Beaded Bracelet