What I Wore To...

Office outfit inspiration, plus some thoughts on why what you wear matters more than you think

Earlier this year — AND last year, come to think of it — I navigated some criticism about my online presence. It’s made me go inward to understand why I share, what I share and when I share. And my in-office fashion was one of those things that, at first blush, seemed like maybe it didn’t fit into the topics I should realistically be sharing. Does anyone care what I wear? Am I trying to sell things? Is it frivolous to talk about fashion or does it somehow take away from my corporate/mentor/advice focused content?

Upon reflection, I’ve reminded myself of a few things lately.

First, what you wear is never neutral. You're communicating something whether you mean to or not: confidence, credibility, how seriously you take the room you're walking into. You hear a lot today about “personal brand” and I am a big believer in this. For me, part of how I present myself as a capable and competent leader is how I dress. I usually opt to dress slightly nicer than I technically need to for most work situations, but I also try to do it with a fresh, not boring point of view. Think: a light colored linen suit instead of a khaki poplin one.

Second, clothes can help you feel good. I don’t need to belabor this point because we’ve read about it in fashion magazines since the dawn of time. This isn’t about getting attention, it’s about feeling prepared for whatever you need to do or whoever you need to be that day. Things that fit, things you like. It’s personal and it’s your choice but you should dress for what makes you feel good. A close friend’s mom used to say that you put on the dress (not sweats) when you’re feeling sick, because that dress can help boost your mood. #truth. For one boss I used to have, she was on the shorter side and so that meant always wearing heels. It gave her the physical and confidence boost she needed to command a room.

And last, I’m not trying to be anybody’s version of a content creator except my own. Actually, the place I’ve found most fulfillment is when I surprise people and break their expectations of what “someone like me” should or can be doing. So… I like fashion and that means occasionally I will share it. That’s it. That simple.

So I’m back to sharing some small bits of fashion. Not because I think I’m particularly trendy. Not because I want to give you advice on what to wear or sell you something. But just because I want to (and, genuinely, many of you have said you like it, too!).

Here’s a round-up of what I actually wore to work and beyond over the last month.

Family Trip to Charleston

Hunter Belle Dress via RTR (rented twice)

tank top (available in solids here) | jeans, old (similar) | jellies (similar for $20!) | sunglasses

Work Trip to Switzerland

Switzerland Outfits: zara suit (old) | floral skirt & vest | dress | slingbacks

Switzerland Outfits: zara suit (old) | floral skirt & VB vest | tanya taylor dress | slingbacks

During my work trip, I was presenting to senior executives and taking several other meetings with my global counterparts. These outfits are ever-so-slightly dressier than I would wear to my office in NYC, but a sign of respect for the weight of the meetings I was taking.

These slingbacks* were a big investment, but they come with me on almost every work trip and are my preferred shoes to wear when presenting. The tiny kitten heel works well for me since I’m already 5’9” and the dark blue denim goes with a surprising amount of outfits.

*In case you’re new here, my theory on life is to “Live in Your Luxury” — hence the name of this substack. It can take a lot of forms, and is usually not about luxury goods, per se. If you’re curious about what I named it this, you can read more here. That said, I do enjoy the occasional luxury purchase almost exclusively invest in luxury items when I travel abroad or buy them secondhand.

black jeans | my most worn sneakers | pink top | marni bag | necklace (my mother’s day present)

Office Days

Office Days

There were a lot of great rentals from RTR this month (use this link to get 50% off your first month) and layering for cooler spring days. I also find myself breaking out of my largely neutral wardrobe more and more, reaching for brighter colors like red and chartreuse (is there anyone who doesn’t like chartreuse these days?).

Outside of the rentals, the only two things I purchased new from these photos are these gingham pants and this Zara skort. The gingham pants have a great stretch and a tiny flare at the bottom. I’ve seen so many cute gingham pant outfits on Pinterest, so envision these getting a lot of use this summer.

I always get asked about my woven mary jane shoes and while mine are old, I finally found a great dupe in a slightly lighter neutral or chocolate brown.

Looking Ahead

Summer has just about arrived on the east coast — my middle son graduated from preschool last week and my oldest wraps up this week. It’s also a tough month for us each year because it’s always busy with work trips, too. All the in between moments seem to be filled with end-of-school events, teacher gifts, and generally things I’m nearly forgetting. I find myself looking for ways to slow down, knowing full well that summer speeds by no matter what we do.

With great gratitude & love.

Xo,

JessAlayne

PS. If you are enjoying my posts, giving this post a little ❤️ makes a big difference in sharing it with new audiences. I’m truly grateful for your support and extra effort!

PPS. In some cases throughout this post, I use affiliate links. If you shop through these, I receive a small commission. Thank you for supporting and shopping through my links.

ICYMI

Here’s a smattering of other posts that you might enjoy. More about my approach to fashion and a reminder to take your PTO this summer.