58 Comments
Sep 15·edited Sep 15Liked by Hillary Kerr

This may be too specific, but I too LOVE a midi skirt and would love a roundup of some of your favorite styles at different price points!

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+1!!

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author

Oh this speaks to me!!! Midis for life.

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Sep 15Liked by Hillary Kerr

I love reading your recommendations but they’re aspirational for me other than the jcrew recs! Here’s my lower budget version - I’ve been wearing Vince platform sneakers as my work travel shoes; they’re comfortable but I feel like the platform is slimming (could be making that up) and they can be dressed up or down. I’ll usually wear with a pair of black jeans (Levi’s ribcage, frame le Jane crop, Hudson Barbara - I know skinny isn’t in but idc because the stretch of this pair is so nice for travel) or the anthro collete wide-leg cropped pants and a nice tshirt and then a sweater, jacket, blazer, or sweater-jacket hybrid. I typically bring a tote in my carry on and use the everlane renew transit backpack which I love; I just can’t get behind a personal item bag that doesn’t zip! I use a Ganni nylon leopard crossbody for my essentials and then stuff it into my backpack before boarding.

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Sep 15Liked by Hillary Kerr

And always a scarf! I’ve been loving a light weight cashmere one I got from quince - super affordable but good quality!

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I get so many Quince ads targeted to me on TikTok, but haven't actually bought anything yet. Have you tried anything else form them? Great to know on the scarf; I need one!

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Sep 16·edited Sep 16Liked by Hillary Kerr

I've been purchasing from Quince for a few years now - have tried many, many things. Overall, quality is good for the price, obviously not same as higher-end designers. But items have held up well over the years. Main thing is fit can be inconsistent, but they have a very generous return policy (365 days) so I always buy multiple sizes and return whichever. I recently purchased some great strappy heels that are low (possibly 55 mm as you mention!) but currently sold out. They also have amazing home items - great linen, sateen, cotton bedding, sofas, rugs. Shipping is free but can take a little longer - about 4-5 business days. My favorite, favorite things are their cashmere sweaters. They have so many, great price point, and so soft. I live in them. Dupes for another more $$$ brand. Also purchased their neoprene backpack in olive green and feels very similar to my Dagne Dover travel bag.

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author

Okay this has me intrigued! Thank you for all the insight!

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Sep 15·edited Sep 15Liked by Hillary Kerr

I have heard from friends their woven leather bags are good quality especially considering the price, but the hardware might be a little shiny although not enough to dampen their spirits since it’s such an accessible purse. They found their slim profile cross bodies especially good for travel and limited suitcase space without sacrificing style.

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Black jeans are my everything! I'm embarrassed to admit this, but I haven't tried the Levi's Ribcage; how do you find the sizing runs? Of your lightweight top layer, do you have a fave sweater-jacket or blazer? I'm always looking for new ones.

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I so enjoy reading your newsletter and yearning for your life! I click every link! Usually none of your gorgeous clothes would fit my life as a stay at home mom to 3 in Cardiff by the Sea 😆 but I thoroughly enjoy your writing and style!!! 💗

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author

Gina! Thank you for writing this! I really appreciate it. Also your comment is making me think I should do a story on weekend/casual daytime/non-work outfits?

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Sep 15Liked by Hillary Kerr

Yes please, or work-from-home Zoom outfits that break the pandemic rut of leisure wear!

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Sep 15Liked by Hillary Kerr

You look amazing in the La DoubleJ outfit! Thanks for sharing all of your looks!

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author

Thank you! It made me feel tall! Which was really fun.

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Sep 17Liked by Hillary Kerr

My biggest question - HOW did you fit all of this into a carry on?! Especially that second denim jacket?!

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author

Would you believe me if I told you that I also fit a bunch of workout clothes and additional shirts and lounge pants in too? The suitcase is good!

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Sep 17Liked by Hillary Kerr

Whichever advertiser got the meeting with your leather midi just doubled their 2025 ad spend

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author

Ahahhahahahahah from your lips to their ears.

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Sep 15Liked by Hillary Kerr

Love reading each week, and I thank the universe for the resurgence of newsletters. Thoughts on reware-ability of signature prints like the La Double J look (which is amazing on you)?

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author

Oh my gosh I hear you on rewearing, esp because it's something I do a lot of. One good thing is that it's a skirt and top, which means I can get additional use out of the pieces. I'm already planning on wearing the skirt with the denim snap-front Alexa Chung x Madewell shirt I wrote about last week, and my old suede cowboy boots, and I'm looking for a chocolate thin wool sweater to wear with it, because I think that would be cool too? The top would look good with my vintage 501s, I think. Also, I have realized that 1) People don't pay as much attention to outfits as we think they do, so I don't feel weird about wearing it a bunch? And 2) I'm hoping to covey this via the newsletter, but I re-wear stuff all the time because I like my stuff, even though that's not very "fashion" of me to not always be new.

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My go to work travel outfit is a maxi or loose midi dress - unless it is deep winter, in which they’re not appropriate. They are comfortable but always look put together. If I need them more work-ready, a belt is always my friend. I can usually wear them with white tennis shoes or also my pointed toe Rothy’s. And a light jacket or a scarf will do, if I need some warmth or layers. Also do not take up much space in a suitcase because it is one piece of clothing ;)

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author

I really need to try those pointed toe Rothy's. So many of my fashion friends swear by them, but I've not gotten the sizing right. How do you find they run? Totally agree on wearing your biggest layer!

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Sep 15Liked by Hillary Kerr

FYI, I believe they have a store in Pasadena!

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Sep 15Liked by Hillary Kerr

They also have a storefront location on Larchmont between Noah’s and Great White!

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author

ooooh!

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Just coming on to say I love how you mix high and low! Your style feels like a great combo of approachable and inspirational (which is a welcome departure from many other fashion substacks that feel so so out of touch). Ty!

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author

Well this is truly my hope and dream, and I appreciate your kind words so much. Truly.

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Sep 15Liked by Hillary Kerr

Love your newsletter-thank you for all the love you put into it!

Travel outfit in US

Tailored joggers (pockets-yay!), tshirt, long-sleeve heavy T (if going to warmer climate), cashmere scarf/pashmina,Jean jacket or heavy denim coatshirt. Packable down jacket if traveling to somewhere cold and swap Tshirt to merino wool sweater.

Travel outfit long haul flight:

Compression leggings, skirt, aforementioned top combos :)

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author

Wait, compression leggings?!?! I need compression socks, this is a reminder!, but talk to me about the leggings? Are they just like regular workout leggings or specific for blood clots etc.? And are they comfy? And bless a tailored jogger; do you have any favorite brands? Always looking!

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Sep 15Liked by Hillary Kerr

Love this one! I appreciate that you repeat items because it shows you actually enjoy them and the price point is warranted! Can you share your favorite NYC hotels? I lived there for almost a decade yet when I return for work, I struggle to find the right spot at a decent price point. Hope to hear more!!

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I have stayed all over town, but I find myself going back to The Bowery over and over again. The location, service, and ease of getting a car/cab make it easy for me to be loyal, but I also know that my hotel priorities aren't everyone's! I also really liked Nine Orchard when I stayed there recently.

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Sep 15Liked by Hillary Kerr

Forever having a tantrum that a $248 Doen dress translates to £278 on the UK site.

Work travel... for the last decade I've been around the financial services world, albeit in the sustainability side of it, so my work travel outfits have tended to be some variation of a dress and a jacket, with that jacket becoming less formal as the years have gone on (and if I'm not going to an event where I'll be wearing the jacket during the event!).

I've just moved into academia, so who knows what the future holds...

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author

I hear you on the tantrum! I used to love shopping Matches for the benefit in reverse. Sigh. Congrats on the career move! Personally hope that means more tweed, but I'm silly like that? Am I wrong to assume it's slightly more causal in academia? But tailoring still is supreme?

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Sep 15Liked by Hillary Kerr

I'm absolutely digging out the knitwear. I'm a student rather than faculty so no need for tailoring - but I also don't necessarily want to dress like the 18 year old undergrads! (Taking a sabbatical from corporate life to go back and get a Master's).

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author

OH EVEN BETTER!!!!! Maybe I'm crazy, but this feels like it would be such an incredible experience. I feel like I would be such a better student if I'd taken more time before grad school. Congrats to you on the sabbatical/scholastic journey!

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Sep 17Liked by Hillary Kerr

Absolutely! It has a real “taking my life into my own hands” feeling to it. It’s part of this wider ‘project’ I’m calling ‘30 on purpose’ - I’m happening to 30 instead of letting 30 happen to me.

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author

I love everything about this!!!

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I love hearing about the products but also the why. Thanks for sharing.

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Sep 15Liked by Hillary Kerr

I've got to ask: how did you pack the ruffled skirt and La Double J outfits in a carryon with everything else in there? Did you have a garment bag too? Lots of steaming at the hotel? The ruffle on the skirt looks tricky to pack. Did you find enough difference in the barn jacket and the denim to have both (vs wearing the denim on the flight and no barn jacket)?

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author

So the skirt is a wool blend, and it's a pretty sturdy material, so that one is on the easier side. I still steamed it when I got to the hotel though, but it's a pretty forgiving piece. For the La Double J. I packed them on a hanger in a garment bag, and then steamed at the hotel. I stay at The Bowery a lot, and have a note in my reservation file that I would like a rolling rack and a steamer in my room upon arrival, which helps. When I check in, I immediately unpack/hang everything on the rolling rack, then steam it all, so that everything feels sorted from the jump. And the Nili pants that I have are the black ones and they're a cotton-blend twill, not denim, and are darker in person then in the photo. Does that answer your question? Let me know if I'm not being clear enough; the coffee hasn't fully kicked in today.

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Sep 15Liked by Hillary Kerr

Love these looks! I just got my colors done and they suggested chocolate brown- that event dress is lovely!! Now to have an event.

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author

What the experience fun? I'm interested in doing it, mostly because I think there are colors I don't wear because of silly baggage/habit. (This is funny, but my mom always wore bright colors, so I think I erred black/gray/white as a teenage rejection, and I need to let that go. Also (again with my mom) she doesn't like darker blues or camels or neutrals, so I've always stayed away for some reason?)

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Sep 15Liked by Hillary Kerr

So many gems in this letter! For the Doen sweater and dress, do you go true to size? Canadian Thanksgiving is coming up and that dress will be perfect! Also, the polka dot skirt is perfection!

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author

Yes, TTS for me. That said, I can wear both a S + M in Doen, and choose my size based on how I want the vibe to be. I wanted the sweater to be a bit more fitted, so I kept the small, and wanted the dress to not be too fitted, so I take a M there.

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Sep 15Liked by Hillary Kerr

Yay! So good to know!

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