Fashion Trends

What You’re Shopping For, September 2022 Edition: Vol III.

By: Jen Shoop

*Image via.

Q: Outfits for me and said (almost) one-year old for family photos. End of October, taking photos outside with hopefully beautiful changing leaves in the background.

A: I had a few variations on this question and will try to answer all here! I would wear a patterned fall dress like this or this with suede boots and put the little in a bubble/dress in either a solid knit or contrasting fall pattern. (Bellabliss has great options, too, for girls over 2, like this, this, this — layer the latter of a white blouse.). As long as there are similar colors, and different scales, I promise it won’t be too busy — just interesting and intentional and fashion-focused. Have the men in the family wear solid colors/tweed to ground the look. This or this for a little boy would be perfect.

Q: Striped sweaters for fall.

A: Gap, La Ligne, COS, or Toteme!

Q: Would love recommendations for “milestone” gifts to get oneself (or for ideas to give a partner) to commemorate a special occasion, promotion, birthday, etc. Was thinking an investment piece of jewelry or handbag (or open to other ideas!) Something timeless but “meaningful” and can be passed down. Ideally under $3K but we can flex 😉

A: An Hermes watch! This is one of the best investments I’ve made in my own wardrobe. I wear it close to daily and it elevates even a simple tee. This is the exact style I have. Some days I contemplate buying a new wrist strap since the solid leather does scratch and show (as the saleslady put it) “patina.” But it also looks kind of fantastically lived-in? Anyway, a more practical Magpie might prefer the pebbled variation. Another great buy: a classic pearl necklace from Tiffany or Mikimoto. They never go out of style and accommodate any age. If you have a more whimsical sensibility, you must check out the fabulous jewelry from Brent Neale. She is so inventive and no one is making jewelry like her (or, well — now there are lots of copycats, but she is a true original). These will definitely be pieces coveted in the future and will likely have a strong secondary market (though you will probably won’t to hang onto it!). Her mushrooms already have a cult following! For something more sentimental/romantic/feminine, look at the beautiful pieces by Aurelia Demark, many of which can be customized/personalized.

Q:  I need a good quality dress for some upcoming black tie events. I’d love to find one great piece that can be styled in different ways. I haven’t had a formal event since COVID, and right now I’m thicker than I’d like to be. Depending on the fit, I’m size 10 or 12, so I need something fundamentally flattering. Under $1000. Any genius ideas?!? THANK YOU!!

A: I would look at the brand Chiara Boni La Petite Robe. This label is known for its elegant, last-forever styles that flatter a wide range of body types, ages, etc. This one is a best seller for a reason — so elegant, so flattering, so timeless. Love the saucy decolletage but then demure sleeves. I also LOVE their velvet pieces out for fall: this looks like Lanvin and would look insane with big statement earrings. You can add a little edge with fun earrings like these, which I personally own and am obsessed with; they add just a little spunk but are very lightweight. I know some people are allergic to strapless, but this is divine, too.

Q: My firm (social impact investing / venture capital) is doing a firmwide outing to a resort in Mexico in March. Spouses / significant others / etc. are invited also. There are dinners every night including a gala dinner the last night (4 nights total). I have no idea what to bring. My style leans toward classic with a bit of an edge. I’m in my mid 40s and need to be able to wear a bra with anything that I pack. I work with mostly middle-aged men. And, I live in Chicago (and prefer mountains to beaches), so the likelihood of me wearing anything that I buy for this trip frequently enough to make it worth spending lots of money is slim to none :)! I’d love to stay under $150 / evening if I can (maybe a bit more on the last night). 

A: I would raid the Farm Rio sale section — tons of spectacular pieces, like this and this, that can be worn with bra and feel appropriate for dining with colleagues. A solid white dress like this could be fun/chic with bright sandals or earrings, and could be worn day-to-night (just swap into wedges/espadrilles). Now is a great time to be buying warm weather clothes because so many epic pieces are on sale…a few other great options:





Q: Fall jackets, jeans, and knee boots.

A: I’m in the same mode. I’ve done a few roundups on blazers, coats, and pants that might be a good starting point, but here are some top-of-the-heap finds I’m contemplating…

Outerwear — this Zara, this Ganni, this Rachel Comey.

Jeans — these COHs, these SLVRLAKEs, these Agoldes.

Knee boots — Isabel Marant Denvees (Target lookalike here), these Silent Ds, Staud Wallys, these Jimmy Choos, and this pair from Schutz.

Q: MOH dress, January in PA. Only reqs: floor length and black. Love under $350 and forgiving.

A: This Aqua is gorgeous and the panel over the back I think keeps it from being too aggressively form-fitting. I love the style/silhouette of this simple one from Anthro, too — it reminds me of the Staud I’ve been eyeing all season. This one also feels elegant, though you’ll have to figure out the v — is it too low? Not sure if it can be worn with a bra, which is annoying. Finally, over budget, but had to include this stunner.

Q: Fall work outfits that can handle office and toddlers — and don’t require dry cleaning.

A: I like a shirtdress like this, this, or this. Easy, chic, machine-washable. I also love this tiered chocolate brown dress, which could be dressed up or down easily. And this sweater dress is under $100 and machine-washable — would look great with tall boots or sneakers. Or pair smart-looking jeans with a statement knit like this or this and some great loafers.

Q:  The daughter of a dear friend has suffered a few miscarriages, but is now set to deliver a baby girl in November.  I want to send a special gift after she arrives.  It could be clothes, accessories, jewelry, toys, maybe something personalized.  Any ideas for something beautiful and meaningful?  Thanks.

A: What a sweet question.  

If she’s a traditional gal, my first thought was one of these gorgeous knitwear sets from La Coqueta (heirloom quality and so beyond precious), OR one of the gifts from Tiffany’s baby section — something pretty she can put out on her baby’s dresser and pass on as a memento.  My aunt sent one of these combs for my daughter and it is a treasure.  You can have a lot of them personalized.

Another thought (more practical) would be one of these Jacadi snowsuits — super splurgey (something a lot of moms won’t want to spring for) but great to have on hand for the cold.

Q: Tweed jacket under $200.

A: Lots of great options here, but I especially recommend this versatile Mango and this cute Aqua. If you’re not into the cropped jacket style, you might consider this.

Q: Cords/pants for little boys that aren’t massively baggy (looking at you CPC).

A: Amen! I love Gap’s styles. More of a classic fit — not as skinny as J. Crew’s, but not poufy like a lot of the traditional brands. I also generally like the fit of Janie and Jack and am eyeing this pull on pair from Hanna Andersson.

Q: October wedding guest in South. Husband wearing a tux because he’s a groomsman, but it’s cocktail.

A: Rhode always has great options — I own this in a different pattern, and it’s fun but elegant. Or try this Kay Unger for an Audrey moment! I also love so much of Ulla and SEA right now — this one is gorgeous for a fall wedding, and this one is just fabulous. And sorry to sound like a broken record, but this Staud is perfection with big earrings!

Q: A chic timeless handbag.

A: Lots of great options here, but I still think the APC is a great investment that will stand the test of time. Upgrade picks: anything from Celine.

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8 thoughts on “What You’re Shopping For, September 2022 Edition: Vol III.

  1. To the reader going on the trip to Mexico — RENT THE RUNWAY!!! It was made for situations like this! For your budget (and especially w an introductory promo code) you can get 4 items (plus any extras for a discounted rate) to rent for that time! Then you also aren’t stuck with clothes you’ll never wear again. Hope that helps!

    1. Yes! I love RTR for vacation – I always feel a little braver when I’m on a trip and RTR is a fun way to try new stuff. I always make one of my picks an accessory (like a bag or earrings) so I know that SOMETHING is guaranteed to fit!

  2. Q for you. While looking at the Gap Sweater dress above, I was thinking about how I could wear it in the dead of winter to work. What are our thoughts on tights these days? I was a tights devotee pre-Covid, but I didn’t reach for them at all last year! Do we still like them? If so, what brand or style? I always wore black tights but wondering if a brown or taupe shade would be better? I’m also moving away from black… nothing wrong with it. I just had the light bulb moment that I look better in warmer shades. TIA!

    1. Hi! I am still pro-tights, but I also am an only-wear-black-tights gal (personal preference). I really like opaque black ones, especially the Spanx ones (“Tight End”). I have heard really good things about the brands Falke and Wolford for hosiery, though. Nellie Diamond wears opaque black Wolfords with every color/pattern in the book and I love her vibe — see here for some examples:

      I also on occasion like patterned tights, like the ones from Gucci or ones with dots/checks, but then I think you really need to pair only with black or a solid color or it’s too much.

      Hope this helps!


    2. Oooh yes, pls advise re: styling a sweater dress!! I have one from last year (navy, slim fit, knee length from Boden) that I’ve hardly worn bc I’m stumped. So far have worn with bare legs and loafers. But I have the same tights question as Sarah Katherine. Plus – if I wear tights, then I need a slip, right? Otherwise the dress sticks to the tights. And does it need to be spanx, so there’s no visible tights waistband?? And what colors to wear with navy??? And shoes?? Not sure my brown knee high riding boots are quite right. Nor my flat black ankle boots. I’m stuck with flare shoes/boots bc of foot problems…

      1. Love the bare legs and loafer situation! I would not wear a slip beneath the sweater dress — I feel like that would cause extra clinginess and clumpiness. I would use an anti-static spray like this:

        I don’t think the tights need to be Spanx necessarily, but just make sure you can’t make out the outline of the tights waistband, per your note! I would also wear black tights with navy, personally! Navy and black are great together. C.f. Nellie:

        I would pair with black booties. Something like this for a classic/polished look: or you could get in on the cowboy trend with these ( or try an embellished lug soles for a modern/trend-forward/edgy take ( or


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