Dressing for Business Doesn’t Have to Suck

I’m almost always disappointed by the business clothes I pick out for myself.

I have a blind spot when it comes to imagining what would look good on me, so I do one of two things:

1. I buy the same dull pieces from the same dull stores (basic cardigans, basic t-shirts, basic jeans).
2. I go completely off the rails and buy something that feels audacious (a one-sleeved blouse in a turquoise bird print! An asymmetrical neoprene shift dress!) but ends up hanging in the back of my closet unworn with the tags still attached.

For me, the best shopping experiences are ones where someone with a great eye can tell me what I need, because hunting for new clothes is not a high priority right now.


My attention needs to be focused on work and making myself successful, not on shopping.
But I still need to look and feel professional when I meet with clients and partners. And since I’ve moved to NYC and work with impressively stylish and creative people, I’ve felt pressure to look like I belong at the table.

I’ve tried online personal shopping services in the past, but they haven’t hit the mark for me.
The selections were usually styled for much younger (and taller) women and were mostly impractical for professional settings.

So when I heard that June Ruby had launched their own personal shopping service, I was thrilled.
June Ruby was founded by Michelle Rotter, a former Google co-worker of mine and style role model who helped me find my way through the wilderness of business casual when I first joined the corporate world in my mid 20s.

Michelle had perfected a look that was chic but not intimidating, professional but not dull, feminine but not frivolous.

She also knows that everything you wear in the workplace needs to be comfortable.
There’s nothing worse than a day of back-to-back client meetings in a pair of pants so uncomfortable that all you can think about is the moment you’ll at last be home and can rip them off.

In anticipation of an important meeting, I had ordered a blouse from June Ruby and shortly afterwards Michelle emailed me asking if she could include a few other selections that she thought would work well on me, no obligation.

Are you kidding? Of course I would! This was my dream shopping scenario — I answer a few easy sizing questions and someone with much better style does all the work.

When I got my June Ruby box a couple days later, I was delighted.

Michelle had pulled pieces for me that fit my minimalist style, but pushed me enough out of my comfort zone that I wouldn’t feel boring.

You can tell that June Ruby caters to working professional women. Almost everything was black or white and could be mixed and matched several different ways, so if you’re going on a 4-day business trip, you’ll have plenty to wear but need only a carry-on bag.

Another big surprise for me was the pricing and payment situation. Michelle had sent pieces that were on sale as well as some full-priced items. And June Ruby didn’t charge my credit card up front for the full cost of the box — I would be charged later just for the pieces I kept. This hasn’t been the case with other personal shopping services I’ve tried.

I was first drawn to the Smythe windowpane check blazer, which felt like a throw-back to the ’80s Working Girl era, but with a less campy modern feel.

Smythe makes a KILLER blazer that will last years.

I value simplicity but I also like details, and the leather elbow patches have a nice finesse.
I have one other Smythe blazer I bought two years ago, and I still wear it constantly. The construction and craftsmanship of Smythe is unparalleled.

This blazer one of those perfect pieces that I’ll be able to wear for many seasons and easily mix with my existing wardrobe.

I paired the blazer with a Joie silk blouse that’s breezy and delicate with a snakeskin print that completely masked my sweat stains on the 90-degree day I wore it!

Running to a meeting in NYC and not arriving looking like a hot, sweaty mess is a minor miracle.
Shopping for pants is always frustrating for me. I’m 5’ 2” and 90% of the jeans I try on don’t fit. They’re designed for people with longer legs and torsos.

But the white James Jeans capris Michelle selected are short enough to hit right at my ankle so I didn’t have to have them hemmed. She understood my #shortgirlproblems and saved me from additional cost and frustration.

The jeans also stretch generously, so if you’re sitting on a flight for four hours they won’t give you deep vein thrombosis.

I loved the super-soft Velvet scoop neck tee Michelle included.

Velvet makes a super-soft tee that can accommodate many different proportions. AG makes the best jeans ever for business casual.

Typically I stay away from scoop necks because they dip too low on me, but this tee worked on my body.

It’s one of those essential versatile pieces that works under a jean jacket or a tailored blazer. And it’s fairly long, so you could wear it untucked with leggings.

I’m a fan of jeans that look polished enough to wear to a client meeting, and these black AG Stilt Crop jeans are super luxe.

The fabric feels like velvety microfiber and stretches without bagging at the knees.
They look nice with flats and sneakers, too.

Wearing dresses make me incredibly uncomfortable. I wear them only on special occasions, and even then I feel like I’m wearing a costume. To me, they feel impractical and distracting.

Splendid wrap dress is so stretchy and soft.

But this Splendid faux wrap dress was totally the opposite: easy-to-wear and not constraining, the fabric feels like futuristic jersey. It hit right at the knee, and though the skirt looks like a wrap, it’s actually a full skirt with a flap up front, so if you’re trying to catch a cab on Madison Ave in a stiff breeze, you’re not giving everyone on the block a free desnudas show.

Getting the June Ruby box saved me from a couple of days of wandering around stores and hunting and pecking online trying to find something new that feels like me.

It’s also fun to be surprised and delighted by the selections. What better shopping experience is there than to have someone who gets your style help push you in an unexpected but welcomed direction?