What to Wear When It’s Too Late for Sandals and Too Early for Boots
These versatile closed-toe shoes make that awkward stretch between summer and fall much easier to dress for.
Office-appropriate and particularly forgiving between pedicures, a versatile closed-toe shoe is the kind of wardrobe workhorse every closet relies on. In fact, it’s worth having a few in rotation. They’re also an unexpectedly smart choice for late summer, when you’re not quite ready for boots but sandals can start to feel a little too summery. A loafer, ballet flat, clog, or other closed-toe silhouette adds just enough coverage to make lightweight dresses, skirts, and trousers feel ready for the season ahead—without committing to heavier fall footwear before the weather calls for it.
Better still, these styles adapt easily as temperatures shift. Wear them now with bare ankles and breezy fabrics; later, add socks, tights, denim, and heavier layers.
Whether you’re filling a gap or refreshing a tried-and-true favorite, the options ahead span practical shapes, textures, colors, and materials at a range of price points. Consider this your blueprint for finding the pairs that will carry you from the last hot days of summer into fall—and earn their keep long after.
Margaux’s classic ballet flat, The Demi, is quite literally the perfect example of this shape and is engineered for maximum comfort and durability. To wear with just about everything, this timeless shoe, especially in black, will be a go-to for years to come.
Sleek, sophisticated, and extremely comfortable, a Tod’s Gommino loafer, with its signature rubber-dotted sole, has been a mainstay in the closets of the uber-stylish, including Princess Diana, who was photographed in several colors of this shoe.
No. 6 has held firm as the authority for the NYC downtown set and it-girls for years. This clean, no-frills clog shape remains a bestseller and looks great with jeans and a tee in the warmer seasons, as well as with a sweater dress and socks on chillier days.
A classic penny loafer is an iconic shape that GH Bass truly does best. Unfussy but always polished, this shoe has remained a classic for a reason. With jeans, a dress, or even a baggy suit, you’ll find there is very little this shoe won’t go with.
A jazz shoe is the hot new silhouette when it comes to stylish flats, and J. Crew's offering is, of course, perfect. Slim to the foot with thin laces and no heel, this shape is chic with jeans and a sweater or a breezy silk dress.
Reformation’s Calista slingback is a polished work shoe with an elevated, pointed toe that distracts from the fact that it has only a hint of a heel. Ideal for commutes and totally cool for happy hour, this all-day shoe will be a power player pairing with a go-to suit and easy silk dresses.
A flat in a woven mesh is a great way to add texture and interest to an otherwise simple look, while providing ventilation on hot days when sandals may not be appropriate. Push the look even further with layering ideas like adding a contrasting colorful sock or a ribbed tight in a neutral during transitional seasons.
This ballet-flat-Stan Smith hybrid is a super modern take on the iconic sneaker style. With the heavy rubber sole and laces removed, this iteration is sleek in shape and hugs the feet in a way that makes movement nimble and freeing. Wear them as you would a ballet flat or a sneaker, since they are, after all, equal parts both.
A gorgeously simple leather slip-on loafer with no flashy details other than its beautiful construction is the piece every minimalist closet needs. This pair from Banana Republic will be one to grab again and again.
Super girly but also super practical, Loeffler Randall nails the need for a feminine sneaker packed with style. This version with a Mary Jane strap in a playful leopard print is a fashion-forward sneaker for those who might not naturally gravitate toward sportier styles.
A polished iteration of a boat shoe makes it more "desk-side" than dockside, and this delightfully two-toned pair from Tory Burch is the one to grab. Swap summery denim shorts for fitted trousers and a baggy sweater, and you have yourself a breezy but sophisticated office look.
A pointy-toe flat is an edgier shape made even cooler with the addition of grommets for an 80s-feeling, slightly rebellious look. The hardware pops on an all-black look, bringing it from somber to sexy in a snap.
Known for their easy-to-wear and easy-to-love travel staples and wardrobe basics, Leset brings the comfort of their ponte pieces to their footwear with the Louis sock shoe. This sleek, soft, minimalist wonder cuts right at the ankle and looks great with trousers or leggings in the office or at brunch.
A satin slipper is the ultimate cool-girl effortless shoe that begs to be packed for a wedding weekend away. Here's why: sophisticated with jeans or leggings for the travel portion, they also pull double duty for cocktails or even the main event, depending on the dress code. Grab one in a punchy color for extra impact.
Sperry, the iconic boat shoe purveyor, has that shape on lock, but their fringed "kiltie" moccasin-esque in soft suede is a sleeper hit. A more bohemian-meets-prep kind of vibe, these are great for off-duty moments with flared jeans or a floral dress and a scrunchy cotton sock.
An open-backed heeled mule style is a breezier hack for warm office days without having to bare your toes. The mix of contrasting neutrals in this woven Simon Miller pair adds a textural touch to an otherwise monochromatic outfit.
Belgian Shoes, the ultimate IYKYK of Upper East Side preppy-core, do make a gorgeous loafer whose status lies in its gorgeous handcrafted product (and the adorable bow detail isn't bad either). Go for the whole look with khaki and a crisp button-down, or flip it on its head with ripped jeans and a baggy sweater for a bit of a grunge edge.
A Margiela Tabi flat is an iconic shape that most serious shoe collectors may already have, but it is a bucket-list shape that budding fashionistas will be highly coveting. The classic split-toe shape is subversive and recognizable, and silver leather brings this it-shoe to a whole new level.
A textural sheer flat can be a great alternative to a heel in dressier or more serious moments when sandals might be out of place. These dots add a playful element to a very simple black dress but are still super refined.
A woven lace-up shoe is a casual yet beautiful option for those seeking a more rustic footwear choice for travel or off-duty living. These stunners from Freda Salvador are striking in white, which will pop in an all-navy or chocolate-brown monochromatic outfit any time of year.
A Venetian velvet slipper with contrast piping adds a well-traveled sophistication to any shoe collection. Formal enough for a cocktail event and comfy enough for a weekend lunch, these colorful classics add welcome texture and class.
A soft suede woven flat is a season-less addition to any shoe closet, no matter how vast or pared down. The subtle texture takes a simple look in neutrals or adds contrasting interest to a print, they really look do work with just about anything you want to pair them with.
A classic Mary Jane in simple leather is a must-have for anyone seeking a timeless, more feminine flat shoe. This pair of Sam Edelman shoes is the perfect shape and has an interesting buckle that still reads super classic. Pair them with a skirt or dress, or make sure the pants are short enough to show off the strap detail.
