Forget statement sneakers — there’s nothing quite like a good ol’ pair of menswear-inspired shoes to inject a touch of cool-girl flair into dressed-up or dressed-down duds. Whether it’s their androgynous appeal or the effortless way in which they tone down frilly feminine pieces, we can’t say — but wingtip Oxfords are a wardrobe staple we simply can’t live without. While you can totally do the hipster chic thing and style them alongside skinny high-waisted jeans, a chambray shirt and oversized cardigan, why stop there? The styling opportunities are endless. This week, Style Resolutions is showing you three fresh ways to wear these iconic kicks, taking you from the boardroom to the bar and Sunday morning brunch in style.


How to Wear Wingtips for the Office


Earning a few extra brownie points with HR is as easy as stepping into a pair of silver wingtips. Every good outfit starts with a killer pair of shoes, and this high-shine set nails it on both the classy and cool fronts. Let your steppers dictate the rest of your OOTD, opting for other RN iterations of office essentials. A classic white button-down gets amped up with asymmetric ruffles, while tailored trousers go bold with a relaxed silhouette and an artsy pattern. Pop on a belted blazer for a touch of extra polish, then show off some of that fun-loving personality of yours with a bright tote bag and modern brooch.

Cole Haan Jagger Wingtip Oxford ($198) + & Other Stories Wide Leg Trousers ($95), Zara Pinstripe Jacket ($169), H&M Ruffled Blouse ($50), P.A.R.O.S.H. Portnek Brooch ($112), Whistles Java Colourblock Leather Tote ($330), Warby Parker Hadley ($145)

How to Wear Wingtips for a Night Out


It’s time to trade out tried-and-true pumps in favor of low-riding lace-ups that will keep feet comfy while elevating your style game to the next level. Quicksilver Oxfords will do just that, especially when styled alongside a floral jumpsuit and jewel-tone satin robe. For a serious after-hours edge, go all-out glam with a shimmery bib necklace and glitzy embellished clutch. Can you say #goals?

Cole Haan Jagger Wingtip Oxford ($198) + Zara Print Jumpsuit ($50), Mango Satined Robe ($120), Nasty Gal Let’s Get Rocked Embellished Clutch ($48), Deborah Lippmann Nail Lacquer in Lady Is a Tramp ($18), BaubleBar Electra Choker and Bib Set ($62)

How to Wear Wingtips for the Weekend


Off-duty takes on a whole new vibe when you swap out your go-to sneakers or fancy flats for a seriously chic pair of metallic wingtips. For an unexpected look that’s guaranteed to earn you some major style cred with your crew, pair the upscale steppers with a playful denim pinafore and striped sweater with a subtle ’70s aesthetic. Take the mid-century inspiration even further for an afternoon of errand running by rounding out the look with an embroidered top handle bag and a military-inspired shacket.

Cole Haan Jagger Wingtip Oxford ($198) + & Other Stories Striped Long Sleeved Top ($45), H&M Cargo Jacket ($50), Madewell Denim Hillview Dress ($128) , Zara Fabric Mini City Bag ($50), Mango Metal Pendant Earrings ($20)

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