Alexandra Martin is a wearwell stylist living in NYC. When she ’s not creating stylist picks for wearwell members, she enjoys cooking old-school vegan health food, reading historical nonfiction, diving into astrology, and hanging out with her beloved friends.
Hailey Bieber has the kind of off-duty model style that other off-duty models aspire to. Hailey flew under my radar for years. When I started working as a stylist, I had to catch up fast because she was the number one name I heard from people when I asked which style icons they wanted to emulate. And it makes sense, her style is effortlessly cool. She's famous for mixing oversized with snug, pairing dark tones with brights, contrasting feminine and masculine pieces, and letting a dramatic silhouette keep the focus by accessorizing with classic embellishments.
Hailey’s looks feature pieces that mix and match well, making her street style the perfect inspiration for a young, fun, capsule wardrobe! When most people think of capsule wardrobes, their mind immediately goes to neutrals, black, minimalism, and simple basics. But a capsule wardrobe can be built around any aesthetic.
Read on while I share how to choose foundational wardrobe pieces inspired by Hailey Bieber, sustainably of course, from wearwell!
Inspired by menswear, worn solo or in a pair!
Step one: find some great menswear-inspired pieces like the kind Hailey loves! The Adalee Trousers and Jaspal Boyfriend Blazer look great together or apart and are sustainable dupes for suits that Hailey sports.
Jaspal Boyfriend Blazer, Grey Check
Go up a size in the jacket if you share Hailey’s love of oversized outerwear or stick to your usual size if you want a look more subtly inspired by her. The Emerson Striped Trousers are another option for a touch of boyish charm.
Emerson Striped Trousers, Beige
Wear them with a cropped sweatshirt (size up!), dad cap, and sneakers in a bright contrasting color to nail the Hailey menswear vibe.
Baggy Bottoms
That aforementioned oversized silhouette is key to Hailey’s style and wearwell has so many jeans and joggers that are right at home in this aesthetic.
Fillmore Boyfriend Jeans, Vintage Faded Blue
For baggy denim, I love the Fillmore Boyfriend Jeans in Vintage Faded Blue or the Alexis Twill Trousers.
Alexis Twill Trousers, Hazelnut
For Hailey-inspired joggers, check out the Jesse Double Knit Joggers, the Willow Joggers, or The Everyday Jogger.
I suggest you size up to achieve her signature look - the baggier, the better! Top off the whole look with a bucket hat to really commit to Hailey’s casual uniform.
Tight And Bright Up Top!
What’s the secret to looking great in relaxed and oversized pieces? Balancing your silhouette with some fitted pieces! Hailey tempers the menswear tailoring and baggy sweats with tops in shrunken fit and bold colors, so let’s play it that way! Reach for the Rhea Rib Crop Top, the Yoga Scoop Crop Top, the Kenzie Top, or the Billie Box Top to get Hailey’s street style.
Yoga Scoop Crop Top, Spruce Green
Extra Basics
Everyone needs basics, but I’m a firm believer that basics don’t have to be bland. Hailey proves that being a little “extra” with your basics packs a style punch.
Val Mini Skirt, Floral Stamp Black
The Val Mini Skirt will look daring just barely peeking out from under an oversized blazer and the Uma Bardot Top will add some femme foxiness to slouchy joggers or jeans.
If you need your bra straps covered, the Claire Tank Top has a similar feminine effect. I love the Aja Dress as a foundational dress that really pulls its weight in this capsule - tuck it under a jacket, wear it over a crop top, or rock it solo.
Finishing Touches
Now that we have a lot of garments that mix and match well to create the perfect Hailey Bieber vibe, it’s time to accessorize! Hailey almost always opts for classic gold jewelry like the Gena Hoops or Serina Hoops and pieces like the Code Link Bracelet or Dana Bracelet.
Many of her handbags and sling bags feature textured surfaces, which are a smart way to subtly add more dimension to her outfits. Check out the Emily Bag and the Audrey Bag for a classic crossbody with a unique detail or shape.
Cruza Sling Bag, Black and White Stripe
Finish off your Hailey cool girl look with a fanny pack like the Cruza Sling Bag or the Felipa Bag.
Check out What We're Loving Now to find more styles that evoke your favorite style icon.
