This Is the Most Comfortable Heel Style, According to Hailey Baldwin
When we caught up with stylist Maeve Reilly a few months ago, she spilled that her client Hailey Baldwin won't sacrifice comfort for the sake of fashion. The 21-year-old model, who co-hosts the iHeartRadio Music Awards today in Los Angeles, is a perfect reminder that it's entirely possible to have both. Baldwin regularly steps out in daring ensembles that mix together unexpected pieces, yet whether it's Bermuda shorts with white ankle boots or baby-blue leggings with a matching trench, she makes it look effortless every time.
"I mean, sometimes I sacrifice comfort, I will say, when it's cold out but you can't cover up the look with a coat," Baldwin admitted when we caught up with her at The Forum while she prepped for the awards show earlier this week. She also confessed that she and Reilly sometimes bicker. "Literally last night I was on my way to go to church and I had boots on and she's like, 'Are you sure you don't want to throw on a heel?' and I'm like, 'No, I'm positive—I'd really like to be in flat shoes,'" Baldwin recounts. "I do tend to want to be comfortable more than not."
So when it comes to footwear, which is usually the first thing to take an outfit out of the comfort-zone, Baldwin has a go-to heel style. "I do wear a lot of booties," she notes. "Heeled boots. I'm a big fan of those."

My mom circa 1975
Who are your 5 favorite people to follow on Twitter/Instagram?@fingermonkey @katefoley @idea.ltd @designmilk @overheardla
What's the fashion essential you can’t live without?My black-on-black Birkenstocks. If that even counts.
What's your desert island album?Radiohead's OK Computer. Or maybe Pablo Honey for something a bit more uplifting if I'm going to be stuck by myself.
What's your favorite WhoWhatWear.com story? California Dreaming with Poppy Delevingne-
If Looking Cool and Trendy Is Your Goal, Copy Hailey Bieber's White-T-Shirt OutfitAlways expect the unexpected with her.
-
I Swear That Dressing Like Hailey Bieber at Pilates Makes My Form Infinitely BetterFive looks I can't stop re-creating.
-
If You're Going to Wear Flat Sandals in September, This Is the Exact Outfit to CopyHailey Bieber approved.
-
Thanks to Hailey Bieber, Everyone Is Buying This Specific Pair of Gap Jeans This WeekIt's $80 well spent.
-
Spotted on Kendall and Hailey: The Pant Color Trend People Are Swapping Blue Jeans ForIt girls with good taste know best.
-
Hailey Bieber Just Said This Classic Print Looks So 2025 When Paired With This Unconventional Shoe ColorUnexpected, yet so chic.
-
Hailey Bieber Wore Vintage Tom Ford Gucci Sandals With the Summer Pant Trend I See Sticking Around Through FallAny pants that look this good shouldn't be packed up just because the season changes.
-
Forget Mules—*These* Are the Classic Anti-Flats L.A. It Girls Wear for Dinner at Giorgio BaldiGood food, great footwear.

