Ask Magpie: Styling Loafers, School Drop Off Outfits, + Fall Event Wear.

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Q: I’m considering the Quince lug sole loafers in bone: this one is a wild card for me as it’s not what I naturally gravitate towards, but it gives off such a cool vibe…when you get the chance, would you be able to share styling ideas please? Especially to balance out the “heaviness” of the shoe…

A: I knew immediately where to go for inspo: Loeffler Randall. This shoe designer does such a great job of styling and merchandising their shoes in wearable ways, and balancing the feminine with the masculine. I love the way the brand’s founder, Jessie Randall, has styled loafers below with socks (my picks: these, these) to soften the look. If this is too challenging / advanced, I’d omit the socks but pair the loafers with a floaty skirt like this or this and a little cashmere cardigan, or a classic pair of jeans and a feminine cardigan or statement cardigan over a v-neck/scoopneck pointelle tee.

BTW, if you’re in the market for a loafer, I just saw that Rothy’s released a really cute option! Also of course love my Elba penny loafers, LR always has a great assortment (love the ones seen above right), and Jamie Haller is the “It” label to have!

Bringing to life in a few styling frames. You’ll probably notice I own a bunch of the items I’m styling these looks with — really tried to think how I’d dress with my own closet!

CASHMERE CARDIGAN // DOEN SKIRT // BON SHOPPE SOCKS // QUINCE LOAFERS // TOTEME BAG

DOEN TOP // MOTHER HALF PIPE JEANS // PARKER THATCH BAG // QUINCE LOAFERS

HILL HOUSE CARDIGAN // QUINCE LOAFERS // VERONICA BEARD BAG // MARCH HARE WATCH

Q:  What the heck are we wearing for bus drop off and pick up?! It’s a short walk down the block so leggings and a t or sweatshirt seem fine yet so sloppy compared to the more polished parents, or maybe it’s just me haha!

A: I think leggings and a sweatshirt are correct for this time of day and errand! I like the polished sweat suit options from Varley (this with these), Frank & Eileen, and Everlane (this with these). I also just got my paws on this cashmere set (top, bottom) from Tuckernuck and can’t wait to make this my early morning uniform. An easy way to elevate the look: layer with a striped button down (e.g., pair sweatpants with this top and put sweatshirt over top or around shoulders) or finish with loafers. Another option: throw the aptly-named AYR Early Mornings Tee on with your favorite jeans and a pair of slip-on sandals. As comfortable/easy as sweats but a tad dressier.

Q:  I’d love, if you (or any commenters?) have seen any, tips on any affordable (ideally, $400 or under) fall boots with lug or rubber soles, either riding style or with a sensible square heel. I’m a professor in a spot where we do real winter, so that means navigating unshoveled parking lots, treacherously icy walkways, wet stairwells, etc., along with the need to stand and lecture comfortably for hours on end. I’d love a pair of good quality boots that could take that abuse but still look sleek enough for professional outfits (which do, in my case, range from blazers and blouses to “nice jeans.” :)) I don’t think they’d have to be officially waterproof, but I’m looking for something with a truly sturdy sole. 

A: Hi professor! What do you teach?! (You are living a doppelganger fantasy life of mine!) I would suggest the Freda Salvador Brooke boots. So chic, water-proof, and great with jeans. They are over budget but if you use code MAGPIE15, you can get 15% off, bringing the price down to $420. These boots specifically remind me of this pair from Tods, almost 2x the price. A look for less option I’ve heard many people rave about: Sam Edelman’s Laguna. Also waterproof!!

Q: First wedding anniversary gift.

A: For you: this heart pendant with your spouse’s initials or pet name engraved on one side and wedding date on the back. Also comes in a smaller size. For him: one night stay at a local/easy-to-drive-to hotel for a night (if in DC, consider Inn at Perry Cabin, Keswick in Charlottesville, Pendry in Baltimore). Bring the frozen top layer of your cake and a bottle of champagne!

Q: What to wear if you are blessed with tickets to a Joni Mitchell concert in October. I feel like I HAVE to honor this moment with a great outfit.

A: Ooh how fabulous! I immediately thought of Alix of Bohemia’s boho cool pieces. (Different genre, I realize, but I’m going to see Kacey Musgraves perform this fall and I already plan to wear this dress with cowboy boots.) A splurge, but anything from Alix of Bohemia feels pitch perfect for strong female vocalist concert-going — even a top like this with jeans and boots. You can get the vibe for less with the brand Emerson Fry. Love this head to toe look, or this one!, for a Joni concert. This dress would also be perfection.

Q: Tailgate outfits for Boston.

A: A statement coat, layers, flat shoes! I like something like this.

Q: Wedding guest dresses for fall weddings, under $350.

A: I love this, this silky number, this floral, this Doen, and this. I am also obsessing over these silk dupioni skirts from Julia Amory (15% off with JEN-15) paired with a shell if you’re open to separates.

Q: Family photo dresses. For me and 15 month old daughter.

A: A few dresses I love for a family photo: this Cara Cara, this Tuckernuck, this Emerson Fry, this Ann Mashburn, this Ralph Lauren, this Saloni. Depending on what colors you’re going with, I’d pick something coordinating from La Coqueta — e.g., this burgundy style will complement a lot! Or a classic Jacadi pinafore with a peter pan collar top beneath.

If you want to match, you must check out Baybala — lots of sweet mother-child coordinating outfits!

Q: Housewarming gift for someone I just met so I don’t know her taste.

A: This list of hostess gifts (and comments!) are a good starting point. I know you’re asking for housewarming, but I think a lot of these would be sweet for that application, too. My more “generic” housewarming gift is a set of Matouk Auberge towels with the family last name’s initial or Parachute (for more modern-leaning couples). Who doesn’t love a stack of fresh white towels?!

Q: Cocktail dress for my cousin’s engagement party – I’ll be six months pregnant.

A: ByTimo always has great loose-fit styles, like this. A self-belt style might also be a good pick — this (under $300, use code YOUROCK for 20% off), this, and this.

Q: Officiant at a fall wedding – bridesmaids are wearing royal blue.

A: So lovely! I love the styles from Saloni for this — they always seem so elegant, pulled-together, and the tailoring is next level. I love this, this, this. All would tie in beautifully with the royal blue. Vibe for less with these two styles from Tuckernuck: this, this. (Both under $300; use YOUROCK for 20% off.)