Fashion Trends

What You’re Shopping For, October Edition, Vol II.

By: Jen Shoop

Q: What footwear do we wear with the new cropped/not skinny at all jeans? In this nice fall weather I’ve been wearing clogs but once it gets cold…

A: I hear you on this dilemma! I really love the new silhouette of wider-leg cropped pants/jeans with a velvet/suede mule or pointed toe flat like these, these, or these. (Or even my beloved VV furlanes!) I feel like the elegance/elongation of the slightly pointed toe balances out the “stubbiness” of the denim cut, while velvet is just super on-trend, and so it makes the whole look feel fashion-forward. That said, a classic pointed toe ballet like this would be a timeless fit. However — ahh!  I know you live in Boston, so this is going to be super tough for you since it is so cold and I can’t imagine baring even two inches of leg in a Boston/Chicago winter.  So if you need to go full-on boots, I would take cues from this chic pea. I’m not sure how practical you feel it will be to wear high heels with children in tow, in a Boston winter, but I think she’s nailing the look.  If you do go this route, I would 100% endorse LR’s Goldy boot.  It’s a forever piece and I doubt it will ever go out of style.  I’m not sure if you’ve ever worn their boots, but they are made for the long haul.  I have a few pairs I’ve owned for over a decade that I still wear (!!!) and have just resoled once or twice.  Super good investment, and so versatile. If the heel height is intimidating/impractical (side note: just had a flashback to one time wearing heeled boots without realizing I was going to have to walk home with mini strapped to me in the Baby Bjorn…whoops…highly dangerous), I also think a slouchy suede boot like this would look good tucked up underneath the hem (imagine with ecru/white denim).

Or, hot take: you could go with Converse high tops a la the stylish lady above!

Q: Nursing-friendly outfit for my son’s Christening in November!

A: Congratulations, mama! I think a nap dress in the brocade or tartan would be pretty, layered beneath an embellished cardigan. I also love CE Finn’s shirtdresses, which I would style with navy suede pumps, a sweater over the shoulders, and a padded headband. Finally, this Sandro zips down the front and is so elegant!

Q: Shoes to wear with leisure wear that aren’t tennis shoes.

A: I have seen chic peas pair leggings/joggers with shearling Birkenstocks (or this fancy upgrade pair), and all the supermodels are wearing Ugg mini boots with theirs at the moment. (Google Kaia Gerber.). Finally, more of a fashion-forward situation, but I have seen people style leggings with lug-sole boots and boxy sweatshirts and look fab!

Q: Fall family photo outfits for me, son, and husband.

A: So special to have these. I shared some coordinated fall family looks here, but I’m also thinking this corduroy-centric post could be a good launching point for a casual aesthetic. However, if I were having my photo taken tomorrow, I think I’d want to wear a patterned fall dress like this, this, this, or this with suede boots and a padded headband, and then I’d coordinate my son and husband in corduroys of the same color, i.e., if you go with the brown color, these cords and this shawl collar sweater on my boy, and these cords and a fall button-down like this. Resist the urge to match too much — a few different prints in the same/similar/complimentary colors will look pulled-together!

Q: Low key patterned pants.

A: Fun!!! Low key is not in my vocabulary, so just sharing some fab printed pants…




Q: Wedding guest dress for NYE.

A: This velvet Reformation or this Saloni will let everyone know you understood the assignment — both are festive and seasonally-appropriate without being over-the-top. Finish with these shoes and RDR moon/star earrings. (Or, pair those glitzy accessories with this spectacular navy satin dress — wowza! Classic, timeless, and elegant.) If you want to go glitzier, check out this feather-trim MacGraw or this stunning belted sequin gown. Or zhush up your favorite LBD with these fun shoes!

Q: Winter wedding guest dress — formal.

A: Love all these winter weddings! I shared some thoughts immediately above, and there are even more options here. If you are fashion-forward, you might also consider this dramatic statement! For a Charlotte York moment, I can’t even deal with this velvet and tartan RL. Some designer went out on a limb for that one, and WOW. And for something of-the-moment, this velvet wrap dress with spectacular platforms.

Q: New fashion tights.

A: I have gotten wear out of these Gucci logo tights the last few seasons. So fun to pair with an LBD and — this season — black suede platforms or velvet ones!

Q: Casual but cute clothes for college classes. I want to look put together but not too formal.

A: Love this! I would invest in a few pair of jeans/corduroys/pants you love that flatter you (some on-trend ideas here) and then go trend-forward with (but spend less on) knits/blouses. A few great under-$100 finds I love:










Finish all of these looks with clogs like these or these or these trendy clog boots.

Q: Travel garment bag (under $200 preferably).

A: Hope you’re going somewhere fun! I’ve had this minimalist under-$50 one on my Amazon wishlist for over a year after Emily Hertz recommended it from one of her trips! I also have my eye on this Neely + Chloe, but it’s much more expensive. Also a touch over budget, but this Barrington one is customizable and very chic!

Q: Baby shower gifts!

A: I like to combine an item that is really practical (a list of my newborn must-haves here — I also have specifically given these Love to Dream swaddles to like five new moms because I didn’t know about them until a few weeks after my second was born and they were SO helpful — micro was always writhing out of his swaddle to keep his arms up by his face; this enables him to sleep like that but was so snug he didn’t wake himself up with the startle reflex; these Kyte sleepsacks also make a good purchase for when baby has outgrown the swaddle; and if your mom friend doesn’t have an OXO wipes dispenser, she needs one) with something really sweet and mildly frivolous, like this baby sweater, baby pram shoes, or an heirloom-quality outfit like this from Jacadi or this from Luli.

Q: Budget-friendly dress for husband’s 40th birthday party — outdoor, early November, upscale casual.

A: This Target dress! I always get compliments on it, it’s very comfortable, it can be layered beneath a cardigan/with booties if it’s too chilly, and it’s just SO gorgeous. Really reminds me of a piece from SEA. If I had my druthers, I’d pair with velvet shoes to winterize the whole vibe. The Nesli nap dress would also be super chic in one of the fall/wintry prints. And this turtleneck dress could be super chic with tall boots!

Q: Sneakers that won’t get ruined in the rain.

A: If you’re talking fashion sneakers, try Supergas! They are canvas and I’ve heard some people put them in the washing machine! If you don’t want to go that far, you can just scrub with a little powdered tide and a toothbrush, which is what I often do for my children’s canvas sneakers (specifically Cientas and Supergas) and they come out good as new. If you’re talking fitness/athletics, try Nike’s Weatherized Pegasus. I had a pair of these I wore in Chicago because I was always running through damp/wet/slushy conditions and they really do keep your foot pretty insulated, whereas a lot of the other lightweight sneaks I wear are almost like sponges.

Q: Boys’ fleece!

A: I love Patagonia on little ones – the quality and styling is top-notch. Luckily, I’ve been able to make most of my children’s fleeces stretch for two seasons so far, so size slightly up and make it work. I have purchased both the Retro-X style and the Retro Pile styles. Love both — the hood on the latter is convenient. I also like this J. Crew style for little boys (Gap has a similar style for less) and this $22 pullover steal. More children’s outerwear and footwear for fall here!

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4 thoughts on “What You’re Shopping For, October Edition, Vol II.

  1. Jen – looking for something similar to this, which I adore but slept on and now it is sold out in my size.
    Was hoping to wear it to a wedding welcome party in November (make it a little more casual with tights and booties) and then hopefully holiday parties! Any ideas? Thank you!!

    1. Hi Caroline! Oo la la, how fun! A few other similar glitzed-up-but-not-too-over-the-top dresses along these lines…

      Different direction but I like how this one is festive without being too wild, too —

      Feel free to send me more specifications (size, sleeves/not, length preferences, etc) and will keep looking!


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