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First, a heads up that Gap is running an epic 40% off sale! All my top picks here, but I recently ordered this crochet top and this tomato red gauze set (top, pants — avail in petite inseam!), and now all are 40% off! That red gauze set is exactly what I dream of wearing with a bucket hat and raffia sandals for a FOJ getaway. And I just went back and got this Doen x Gap gingham dress…not included in the sale but couldn’t help myself!

GAP GAUZE PANTS AND TOP SET // GAP STRIPED SKIRT // GAP CROCHET TOP // GAP WHITE MINI // GAP SLOUCHY BAG // GAP BANDANA PRINT MINI
Q: Lightweight pants for summer.
A: These dreamy gauze pants, these block print J. Crews (have worn the past two weekends), pull-on linen pants (upgrade pick: Donni), linen barrels from Gap, these white eyelet or seashell trim statements, and these patterned Julia Amorys.
Q: Dress for postpartum newborn shoot in July.
A: Congrats (early)! I love this lace caftan in the most gorgeous lilac color, anything Loretta Caponi (dreamy white or playfully patterned), this Agua Bendita, a floral Mi Golondrina, this Mille (use code JEN15), and of course Doen is always perfect for more of a boho mom moment. Oh, and this Farm Rio!
Q: A cute cover-up for Miami!
A: This Tuckernuck or this La Veste!
Q: Swimsuit that is cute but appropriate for a 50 year old mom.
A: I love the ones from Minnow right now! Sweet, playful, but not too far in any direction.
Q: Wedding guest dress for Italy in September. Dress code is semi-formal.
A: This Julia Amory, this Zimmermann, this Agua Bendita, this Damaris Bailey, this Coco Shop, this Veronica Beard.
Q: Tote to be used for diaper bag. (Will buy organizational insert.)
A: I love the chic totes from Rue De Verneuil! These patterned canvas ones from Timo and Violet would also be sweet. The St. Barths Medium tote is also a great choice, and practical (woven neoprene). The handles do fit over the shoulder! A little more sporty / casual, but I just got this striped Vee Collective tote, and was thinking it’d also be a great baby bag. If you’re looking for something more discrete – more like an everyday tote that can also work as a diaper bag – I mainly used my Goyard and loved it! One of these colorful Mansur Gavriels would also be fun.
Q: Morgan Wallen outdoor concert outfit?
A: SO jealous. Love “Talkin Tennessee.” For country concerts, I like a denim dress (this, this, this) with either a statement sandal or (if you’re committing) cowboy boots from Tecovas or Miron Crosby. The other direction — a breezy slightly boho white dress with the boot. OR do something like this gingham mini with a fun sandal like this or this.
Q: College reunion – day outfit for walk around campus and nighttime look for dinner/drinks/bar in June.
A: For day, I like a polished but playful/colorful daytime dress like this with some easy-to-wear-and-walk-in sandals like these or these. If you’re a little more of a minimalist, try this dress. And if you’re a black girlie, try this dress with these sandals. For nighttime, wear something FUN that comunicates joy and confidence! I like something like this, this, this, or this. Or if you prefer solids, this, with some big bangles or a big necklace. I’d wear any/all of these with a FLAT sandal. I feel like it looks more modern/carefree and is obviously much more comfortable.
Q: Lightweight cotton sweater — preferably oversized.
A: This G. Label or this Alice Walk! The latter is particularly lightweight. I own in a great moss green color. I’d go up a size in this if you’d like it looser/boxier.
Q: Statement designer bag for summer – something a little different.
A: This Prada!
Q: A gift for my mom’s 75th birthday.
A: An Aura frame pre-loaded with lots of family pictures in it. Or an Aurelia Demark necklace, customized/engraved. Last idea: a getaway just the two of you to somewhere you can drive to overnight. I did this just recently with my mom and it was so special. Even just the two hour car rides there/back. So special to have that one-on-one time!
Q: A special gift for a friend’s second marriage. Her home is stocked…
A: I have yet to meet anyone who doesn’t love new luxe towels. Another idea: an extravagant gift card for a date night to a special restaurant in your town.
Q: Haircare/shampoo/conditioner for my kids. My mini has outgrown baby shampoo.
A: We use Pantene Pro-V for our kids! Inexpensive and really good quality — it’s my favorite drugstore variety option and the kids always say “it smells SO good!” If you want something that’s more kid-branded, though, try Ever Eden or Tubby Todd.
Q: Girls trip to St. Tropez!
A: OMG – how fun?! A few pieces that leapt out at me: some Posse linen separates/dresses (vibe for less with Quince), fun sandals with gold hardware, this dress, this tote (look for less here), anything Cala de la Cruz or Ciao Lucia, this cover up, this woven Zara.
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