Dress-and-boot combos are the only fall outfit formula you truly need to master this season. Don’t get us wrong — chic sweaters and jeans are incredibly effortless, but this power pairing comes together in two seconds flat. And did we mention it’s the ultimate double-duty duo? Because yeah — it’ll take you from the office to after-hours outings, no costume change required. Instantly upgrade sweater dresses sans tights with over-the-knee boots, or give a bright midi dress a lift with sassy pointed-toe steppers. From metallic block heels to embellished beauties, consider this your guide on how to wear this season’s most Insta-worthy shoe trend with every dress in your closet.
1. Zara Long Embroidered Dress ($129) + Topshop Mercury Block Heel Bootie ($130): This just in: An embroidered midi dress for desk-to-drinks dressing is non-negotiable. Worn over a silk cami and black slim-fit trousers, it boasts some serious wear-anywhere potential that will resonate with girls on the go everywhere. Prep your day-to-night getup for dance floor shenanigans with modern metallic ankle boots that will add serious pep to your step the second you slip them on. Matte red lipstick and romantic beach waves may or may not be in order to solidify your status as an #OOTD aficionado.
2. Madewell Silk Ruffle-Hem Dress in Windowpane ($168) + Free People Liquid Gold Platform Boot ($198): An effortless silk dress that will win you serious style cred with both HR and your crew? We’re in. With a classic navy color and windowpane check print, this ruffle-trimmed dress gives off those forever kind of vibes that your closet — and wallet — love. While the dropped-hem gem would certainly look amaze with suede Mary Janes or shimmery loafers, we’re partial to these platform booties that are equal parts comfy and retro cool.
3. The Group Streep Dress ($165) + Jeffrey Campbell Bellaire Tapestry Bootie ($185): Lazy girls, unite! When you have to peel yourself away from the couch, you’ll be thankful to have this dynamic duo on standby. Consider this basic bodycon a blank canvas for endless casually cool looks that come together in a snap. Whether you team it with white tennis shoes and a bomber to catch the big game or pair it with these dreamy tapestry boots and a leather jacket for a night at the museum, it’s foolproof.
4. Warehouse Squiggle Print Plisse Dress ($80) + Marc Fisher LTD Jayla Block Heel Bootie ($179): A midi dress with this much personality should be at the top of every It girl’s shopping list. Blame it on the change in season, but we’re craving color to combat gray skies and plummeting temps, and this artsy frock was practically made to chase the mid-season blahs away. Partner the abstract item with architectural ankle boots in a moody shade of burgundy. For a street style-approved look, you best be tossing on a faux fur scarf and longline cart coat FTW.
5. & Other Stories Turtleneck Dress ($95) + Zara Stretch High Heel Over-the-Knee Boots ($80): Our solution to chilly mornings when you just can’t even? A relaxed turtleneck sweater dress. The next best thing to staying snuggled up under the sheets, it doesn’t skimp on comfort or class. Ditch the tights for extra style credit in favor of these thigh-high stunners that add an extra layer of warmth and a subtle touch of sex appeal to boot (we had to).
6. Zara Checked Dress ($50) + Dr. Martens 8-Eye Leather Boots ($155): With a studded shirt dress and classic combat boots on hand, you’ll easily achieve an enviable model-off-duty ensemble. The only thing missing? An oversized denim jacket, mid-calf socks and a knit beanie (with a handful of sassy pins, of course).
7. River Island Yellow Block Houndstooth Print Dress ($56) + Mango Buckle Ankle Boots ($150): ICYMI: Tweed is an essential component for fall, and this color-block frock is no exception. Achieve major #(mod)squad goals by popping it on with a cardi-coat and these bold-buckled ankle boots for a mod look. After-work drinks on the agenda? Say no more: Opt for a dramatic cat eye and sleek hoops to transition the look from on-the-job to after-hours.
8. Topshop Cold Shoulder Floral Mini Dress ($100) + H&M Lace-Up Boots ($50): Found it: the latest addition to your LBD collection. Between fall weddings and harvest parties, this pretty prairie chic dress is about to become your new go-to. For Sunday morning brunch or an intimate indie show, team this cold-shoulder stunner with lace-up booties for a ladylike look with a free-wheelin’ edge. Now all you need is a felt fedora and tassel-trimmed saddle bag.
9. Madewell Lace-Up Sweater Dress ($128) + Kelsi Dagger Clermont Boots ($160): A snuggly sweater dress that feels like a warm hug? Now we’re talking. As the days get shorter and the temps get cooler, you’ll be looking for any reason to stay cozied up in your comfiest duds, and this laid-back combo more than delivers. For extra warmth, layer on a pair of fleece-lined tights (or better yet, leather-look leggings) for just a hint of tough-girl edge.
10. Zara Printed Velvet Dress ($50) + All Black Side-Scoop Booties ($178): MVP style status? Right this way. Take your GNO look to the next level with a floral velvet slip dress with just the right amount of ‘30s flair and sculptural scoop booties. Sayonara, LBDs. Prep for a networking event by throwing a lace high-neck blouse and sleek drop earrings into the mix.
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