"Throwback within a throwback" is how Michelle Obama's longtime stylist, Meredith Koop, captioned an image of the former first lady's most recent outfit. Translation: The look has not one but two different reference points. First, it included the same brooch Obama donned at the Democratic National Convention in August 2008, three months before her husband was elected president. Second, as Koop also revealed in her caption, the color of her teal Hervé Léger bandage dress paid homage to Kailua Blue, the ocean-hued china dinnerware used for Obama-era White House state dinners. Michelle Obama personally chose the color and named it after a town in the president's home state of Hawaii.

Now that we've covered the fascinating backstory, let's get to the key styling choice that ensured Obama's outfit looked thoroughly modern. Hervé Léger bandage dresses peaked circa 2008, but adding the long-sleeve sheer layer under the dress made it look cool and contemporary. Don't you agree? Scroll down to see what Michelle Obama wore for an appearance on Jimmy Kimmel Live! and compare it to her DNC look from 17 years ago.

December 2025

On Michelle Obama: Hervé Léger dress; Jimmy Choo shoes; Erickson Beamon brooch

August 2008

On Michelle Obama: Maria Pinto dress; Erickson Beamon brooch

Re-Create the Look

If you're as obsessed with shoes as I am, you've probably spent a lot of time thinking about which fall 2025 footwear trends you're going to invest in. There's no lack of chic options to choose from, but the one I keep stumbling upon is flat slipper mules. They may be initially inspired by the hotel slippers you find in the closets of luxury properties, but the comparisons stop there. Thanks to the luxe materials and sturdy soles, you definitely won't look like you're wearing actual hotel slippers in these.

My reason for bringing up this particular fall shoe trend is that Michelle Williams was just spotted wearing a pair of flat slipper mules in L.A. heading into a taping of Jimmy Kimmel Live!. Williams made the smart decision to pair her tan suede slipper mules with the comeback pant trend of the year: cropped skinny pants. The once-dated pant trend looks very much the opposite of dated when paired with this effortless, modern flat-shoe trend, so I fully support adding this combination to your wardrobe before fall kicks off.

On Michelle Williams: St. Agni Petit Woven Trapeze Bag ($425)

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Although I’m 5'7" myself, many of my closest friends fall into the petite category. And as the designated fashion person in the group, I'm often the first port of call when they’re in need of styling advice. This week, the group chat was alight as I circulated an image of Michelle Williams styling the petite-friendly shoe trend I've told them all to consider.

Snapped on the streets of New York during a promo run for her new show, Dying for Sex, Williams ditched the dainty ballet flats and Mary Janes dominating the season and instead opted for something bolder: a pair of thigh-grazing, over-the-knee boots.

By allowing the boots to begin exactly where her babydoll minidress ended, Williams created one long, fluid line from thigh to toe. The result elongated her frame—proof that sleek over-the-knee boots can be a game-changer for petite women. Add in a tall, structured heel, and suddenly, there’s not only the illusion of added height but also a pretty boho formula that's surprisingly easy to recreate and that chimes with the mood of the new season. Perhaps unsurprisingly, Williams' boots are from Chloé, the brand leading this boho rennaisance from the runways.

Williams completed her look with a long-line pendant necklace and a rich burgundy handbag. And while this outfit might not follow the typical rules of spring dressing, in my opinion, it’s perfectly suited for transitional weather. The tall boots add warmth, the sleeveless dress allows for breathability, and the overall effect strikes that ideal balance between drama and femininity.

Inspired? I certainly am. If you're ready to give it a go too, scroll on to shop my edit of the best over-the-knee boots below.

SHOP OVER-THE-KNEE BOOTS:

If you're tired of having your feet covered up 24/7, you're probably thrilled that the winter months are behind us. Now that spring is in full swing, the specific shoe trends of the season are starting to emerge, and Michelle Williams just wore one of the freshest heel trends of the year in downtown NYC.

The trend is peep-toe heels, which were prominent on the S/S 25 runways of Miu Miu and Khaite (among others), banishing the trend's "dated" reputation in an instant. Williams, who has been busy promoting her new series, Dying for Sex, smartly paired her black peep-toe heels with straight-leg jeans and a Chanel tweed top. She looked every bit the sophisticated New Yorker, and I predict that this heel trend will be quite popular on the streets of Manhattan in the very near future—especially since jeans and heels are a go-to combination for a great many NYC residents. And peep-toe pumps (as opposed to sandals) like Williams's are a particularly good choice if you prefer to not have your feet super exposed on the somewhat grimy streets of NYC.

Now that you have all the info, keep scrolling for a bit of peep-toe-heel inspiration and to shop my favorite pairs on the market so far.

On Michelle Williams

On Michelle Williams: Chanel top and bag

On the Runway

Miu Miu S/S 25

Khaite S/S 25

Shop My Peep-Toe-Heel Picks

When it comes to airport style, I am all about outfits that are comfortable without sacrificing style, and your shoes are the key component for accomplishing this. Heels are a hard no in my book, as well as any other footwear that makes for a complicated run through the security line. This leaves flat shoes like loafers, ankle boots, sneakers and my all-time favourite: ballet flats. While ballet flats truly never go out of style, they are currently at the forefront of shoe trends at the moment.

I know I am not alone in this preference as evidenced by the many stylish celebrities that are spotted traveling in the timeless flat shoe style, whether it's a Mary Jane style or a studded pair. Besides the ease, they instantly elevate even the most basic of outfits. Just don’t forget to pack a pair of socks in your carry-on to save you from a grimy barefoot walk through security. Ahead, check out eight inspiring celebrity airport looks with ballet flats. Plus, shop some of the chicest options out there right now.

1. Elle Fanning in Satin and Leather Ballet Flats

Style Notes: Fanning has a sleek and chic look that's softened with a pair of pink satin ballet flats with leather details.

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2. Ashley Olsen in Two-Tone Flats

Style Notes: Olsen is effortlessly chic in a camel coat, black jeans, and two-tone ballet flats. As one co-founder behind The Row, it's no surprise she knows how to style flats, especially when her brand's own versions always sell out.

3. Jasmine Tookes in Black Ballet Flats

Style Notes: Tookes understands that comfort is key for any flight. Try a matching knitted set for in-flight comfort, and an easy pair of ballet flats for a delicate touch. You can never go wrong with classic black.

4. Kate Bosworth in Neutral Ballet Flats

Style Notes: For an easy, polished feel, try this look from Bosworth—white button-down shirt, cropped jeans, and neutral ballet flats. Flats in subtler tones will go with everything you've packed.

5. Cindy Crawford in Animal Print Flats

Style Notes: This easy-breezy outfit idea from Crawford requires four pieces: a trench coat, white T-shirt, slim jeans, and snakeskin flats. There are plenty of other faux animal print options too if you like this maximalist spin on the shoes.

6. Elsa Hosk in Shiny Flats

Style Notes: Hosk gives a sleek pair of shiny black ballet flats the model treatment with a statement off-the-shoulder top. Whether you prefer patent leather or something subtler, shinier textures always feel like a statement.

7. Michelle Williams in Pointe-Inspired Flats

Style Notes: Williams took the word 'ballet' seriously when it came to her look. She completed her stylish travel outfit with pretty pink ballet flats that are reminiscent of those actually used out on the vinyl dance floor. Opt for square pointe-inspired picks or those with rounded softer edges.

8. Miranda Kerr in Metallic Flats

Style Notes: Kerr is all smiles in a vibrant printed top, slim black jeans, and shiny square-toed flats.

More Stylish Ballet Flats to Shop Now

When it comes to airport style, I am all about outfits that are comfortable without sacrificing style, and shoes are a key component for accomplishing this. Heels and any other shoes that make for a complicated run through the security line are a hard no in my book. This leaves flat shoes like loafers, ankle boots, sneakers, and ballet flats, my all-time favorite. While ballet flats truly never go out of style, they are currently at the forefront of shoe trends.

I know I am not alone in this preference, as evidenced by the many stylish celebrities who are spotted traveling in the timeless flat-shoe style. Besides the ease, ballet flats instantly elevate even the most basic of outfits. Just don't forget to pack a pair of socks in your carry-on to save you from a grimy barefoot walk through security. Ahead, check out 11 inspiring celebrity airport looks with ballet flats. Plus, shop some of the chicest options at the moment.

1.

Model Jasmine Tookes pairs her black cap-toe flats with an elevated ribbed matching set.

2.

Actress Elle Fanning stepped out in a whimsical look complete with satin ballet flats.

3.

Ashley Olsen is effortlessly chic in a camel coat, black jeans, and two-tone ballet flats.

4.

Angelina Jolie kept things comfy yet polished with an oversize gray sweater, basic black pants, and timeless black flats.

5.

For an easy, polished feel, try this look from actress Kate Bosworth—white button-down shirt, cropped jeans, and neutral ballet flats.

6.

Model Karlie Kloss is the epitome of chic in this retro-inspired outfit. Try a long white coat, a printed shirt, cropped black pants, and a pair of simple black ballet flats.

7.

This easy, breezy outfit idea from model Cindy Crawford requires four pieces: a trench coat, a white T-shirt, slim jeans, and snakeskin flats.

8.

Elsa Hosk gives a sleek pair of black ballet flats the model treatment with a statement off-the-shoulder top.

9.

Actress Michelle Williams completed her stylish travel outfit with pretty pink ballet flats.

10.

Model Miranda Kerr is all smiles in a vibrant printed top, slim black jeans, and shiny square-toed flats.

11.

You can't go wrong with an effortless all-black look like Kate Moss's.

More Stylish Ballet Flats to Shop Now

Greta Gerwig just stepped out on the red carpet at the 2018 Academy Awards looking like a dream. In a floor-length yellow gown, the actress stood out in the bright colour. With the colour perfectly complimenting her light hair and red lip, Gerwig looked stunning… And also reminded us of one of our favourite past Oscar looks.

While this yellow gown was a new look for Gerwig, her outfit reminded us of Michelle Williams circa 2006. At the 78th annual Academy Awards, Williams turned heads in a canary yellow Vera Wang dress with a nipped-in waist, much like Gerwig’s look.

Not only did Gerwig’s dress call to mind William’s outfit from over ten years ago, but even her accessorising seemed similar. Like Williams, Gerwig paired the yellow gown with a sparkly necklace hitting right at the collar bone.

Furthermore, the bright red lip and blonde side-swept bangs were enough to convince us that William’s look might have played a role in inspiring Gerwig’s outfit. Even though they’re more than ten years apart, this unique red carpet look feels fresh either way. We’re so happy Gerwig reminded us of (and recreated) this amazing outfit.

WHO: Michelle Williams

WHO: Greta Gerwig

Related: Everything You Need to Know About the 2018 Oscars

This has undoubtedly been the summer of the straw bag, and if we Who What Wear editors had to pledge our allegiance to just one version, it would have to be the perfect Market Carry-All Basket from new Los Angeles–based brand Dôen. The bag is made of lightweight seagrass and rings in at just $28. It's no wonder that the tote, which was available in both natural and black, quickly sold out. And while it has come back in stock since its release, we noticed that it keeps selling out again in a flash.

We weren't surprised to see this week that the bag has even won over the likes of Michelle Williams, who used it to accessorize a breezy midi dress and espadrilles. Given that you can still sign up for a "back in stock" alert, it seems likely that it will return. And even though fall is quickly approaching, we suggest purchasing it if/when it does, to keep on hand for next year.

Keep scrolling to check out the bag and shop a few of our other favorite baskets.

On Michelle Williams: Dôen Market Carry-All Basket ($28).

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Would you carry a straw basket out at night during the summer? Tell us in the comments below!

Opening Image: Dôen

When a number of heavy-hitting tastemakers, including Gwyneth Paltrow, Rihanna, and Rosie Huntington-Whiteley, all head out wearing white blazers in one week, we definitely take notice. It's not only an indicator that we need this piece in our wardrobes now, but also a reminder of how many different ways you can wear the crisp jacket this season. The white blazer can easily take you from a work event (with satin shorts and pumps) to a GNO (with a silky tank and leather skinnies) to the weekend (with a casual tank and trousers) and that's just the tip of the iceberg. Click through today's slideshow for even more inspiring outfit ideas and shop similar styles now. 

Wearing: Isabel Marant blazer; The Reformation top; J Brand pants, Christian Louboutin heels.