How To

How to Get Dressed Again

Stylists Jill and Jordan on how to get back in a sartorial groove.

COCKTAIL PARTIES, CLUBS, and gatherings are back. After a year of sitting home in joggers, leggings, and pajama pants, we’re all eager to look and feel good at last. But having become one with stretch and fuzz, are we ready to return to the finer threads of yore? Eyeing our now fossilized formal wear with reticence, we look to fashion stylist duo Jill and Jordan for some guidance. From red carpet to editorial, the pair has styled countless fabulously dressed Hollywood folk, including Jennifer Lawrence, Gael Garcia Bernal, Rachel Brosnahan, and Anna Kendrick. Here, the fashion goddesses turn their expert gaze to the slightly more modest, tragically relatable topic at hand: how to get dressed again.

As we reclaim our social lives, what are the best formal pieces that look put together but still feel like the sweats we’ve been wearing at home?

JILL: I think the timing of warmer seasons is great because we’re all pulling back out our maxi dresses and things that aren't so constricting. There's a little bit of wiggle room for us to get back into fighting form and not really have to dive deep into fashion and such put-together looks right now.

JORDAN: My flowy dress collection has gotten out of control but I'm just like, this is what I want. I need an eating dress. I love a casual top — sweatshirt or button-down or T-shirt—with an unexpected bottom. Like a dressier skirt or pant. So I still feel comfortable. And never a heel right now. My feet instantly cramp once they even look at a heel.

JILL: I'm really loving Alexis right now for the warmer seasons. And Staud is great in their materials, also very resilient (for when you wear a Staud dress as your eating dress).

JORDAN: Jenni Kayne makes this one breezy, cotton-linen, no-guesswork Summer Dress that they come out with every season in new colors. The sleeves are the right width. I think I have like three of the colors now. It says dry clean only, but I wash it and it’s fine. It’s the go-to if I ever want to feel put together.

My feet instantly cramp once they even look at a heel.

What are some general fabrics that feel like you’re wearing pajamas without looking like them?

JILL: I started learning how to distress different fabrics and canvases at the beginning of the pandemic and doing natural dyes. And I found that twill is so great because it softens over time. It's a really comfortable fabric for pants. Denim is essentially a twill, just in a different kind of weave. Linen and bamboo are also great.

JORDAN: I also like wearing actual pajamas. Dior gave us these silk pajamas for Christmas last year. I wear the pajama top as a regular shirt all the time. I can't bear to not be in some sort of pajama right now.

[Said Dior pajamas are currently sold out, so they shared a similar pair from D&G]

Jeans, or “hard pants,” can be notoriously uncomfortable, especially the tighter fits. What are some less constricting pairs that still flatter the physique?

JILL: I love the term hard pants. I don’t think I’ve ever heard that. Now I’m like … Yeah ... Hard pants!

JORDAN: We’re going to have to start using that. I’d say Frame jeans look good on every body type across the board. Not to say a singular pant, but there is a pant in there that's flattering for everyone. They have a crop that’s a nice “fashion jean” for summertime. I also love AGOLDE jeans; they make a really good straight leg jean that sits a little bit higher. We did a fitting with a client recently, and she put on a pair and said that they felt like jeans she’d owned for five years. They were soft and comfortable but still looked so good.

JILL: I’m wearing a pair of COS pants right now that I have in every color. These are a soft cotton canvas and they're a bit of a drop crotch but not so much of a drop crotch that my husband gags when I leave the house. It's like a hybrid drop. They’re a really fun alternative to a jean. There's a drawstring waist. So that's another fan favorite of ours.

JORDAN: COS pants are a secret weapon.


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I can no longer tolerate heels higher than my house shoes/errand sneakers. What’s a pair I can wear to a post-COVID wedding or cocktail party without killing my feet?

JILL: We had to shop for a private client and noticed something this week: there's not a lot of super high heels anymore, which I think has to do with the very root of your question. No one is ready. We had this client who asked for super high heels, and we were like, well — there were about two pairs. Louis Vuitton always has a couple lower-heeled styles every season that are really fun. Chloé has great stable platforms. Roger Vivier has a great satin and jeweled “flatform” pair for a wedding. Those are my brands for elevation.

JORDAN: Schutz makes really comfortable shoes that kind of work universally. They have something for everyone. At a good price point. By Far also has really great beautiful lower heels that make anything look put together and chic.

For those still remote working, what are some sharp meeting/interview tops that don’t seem bizarre to be wearing in my living room?

JILL: I’d suggest wearing a camisole under a button down. It's a little bit fresher than a plain T-shirt and doesn't look silly.

JORDAN: And a colorful cardigan over a T-shirt. Color usually looks a bit better on a Zoom. Though we all love our white T-shirts, it just adds a little bit more. Same goes for a washed silk blouse; they just kind of lay right and still look relaxed. Equipment makes a good washed silk blouse. In general, I’d suggest any kind of layering just to make it look like you've tried.

JILL: Madeleine Thompson makes cashmere in full pants and hoodies that you can wear out. I have one that I put on in the morning, run to get coffee in, and basically stay in all day. Great colors, great patterns, great prints. It's an easier way to lean into getting dressed again, to take our normal neutral pieces but then have a little color or print added. And for the button-downs, I love Xírena. They’re super soft, casual looking, but a little bit more thoughtful than just a normal button-down.

For the working parent/at-home teacher/children’s personal chef — what are some nice looks I don’t have to feel precious about (highly washable, stain-proof, kid-crawling-on-lap-proof)?

JILL: We both have kids, so this basically encompasses both of our lives and how we have to dress because anything precious has long since made its way to the back of our closet or the RealReal [consignment shop].

JORDAN: If I have to dry clean it, I no longer wear it. That's my new rule of thumb. If I can machine wash it or hand wash it, then great. But I just found myself not wearing the pieces that I have to dry clean because my kid spills on them and it just turns into a big mess. So a lot of cottons and linens.

JILL: Sea has been making some really great dresses but they're not precious. Great prints, comfortable shapes, and they just make me feel a little more put together. But if my kid throws up or spills on me or comes with their greasy paws I'm like, it's okay! I have a lot of similar dresses from Co too. Slightly higher price point. They make me feel like a girl again. Cynthia Rowley also has done an excellent job in recent years of making these kinds of happy dresses that you don’t have to worry about throwing in the wash.

I haven’t worn a bra in a year. What are some ideas for bras that feel like I’m still not wearing one?

JORDAN: I just discovered this bra that I'm obsessed with. It's Negative Underwear's wireless bra and it's called the Sieve Non-Wire Bra. It comes in these beautiful colors. It's mesh. So comfortable.

JILL: We love Hanro; we love Eres. They make great wireless bras. And COS! COS Makes great bras. So many hidden gems in there.

What are some of your favorite mask designs for chic safety?


JILL: Kaze Origins. You can get every color.

JORDAN: There’s like three shades of blue and two shades of white. Really every color.

Loosening the drawstrings of our house pants, may we now have the confidence to perhaps pair them with a fun low heel; or a dash of color, with a matching jewel-toned mask; or, for now, the shapeless muumuu top it came with, plus a splash of joie de vivre. Baby steps.

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Our Contributors

Sophie Mancini Writer

Sophie Mancini is an editor at Departures. Born and raised in New York City, she holds a degree in creative writing from Johns Hopkins University and has a background as a writer in brand and editorial.

Giorgia Ascolani Illustrator

Giorgia Ascolani is a half-New Zealander, half-Italian content artist currently based in London. She has created content for Zac Posen, Inglot Cosmetics, Prada, and Mulberry, to name a few.

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