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Yes, You Can Pull Off a Menswear-Inspired Blazer—Here’s How
With the help of suiting separates and Power Casual pieces, anyone can rock a boyfriend blazer.
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It’s awards season, which means the Internet is ablaze with red-carpet roundups. As you scroll past images of Michelle Yeoh and Margot Robbie on your way to catch up on current events, you might daydream about what you would wear for your own Cinderella moment. A twirl-inviting ball gown? A slinky silk slip dress? I’d go with something menswear-inspired. Did you see Uma Thurman’s button-down look at the Oscars last year? Chic.
Wearing menswear may be a bold, unconventional choice at formal events, but in daily life, it’s just about as classic as it gets. Still, many women continue to question whether or not they can “pull off” dapper designs and oversized silhouettes. As a menswear enthusiast, I’m here to tell you: Yes, you can. Clean lines, impeccable tailoring, and structured shapes suit everybody.
To ease you into these new wardrobe waters, let me introduce you to the O’Hara in stretch houndstooth. This best-selling boyfriend blazer pairs strong shoulders with a relaxed fit, and our newest iteration is crafted in a menswear-inspired houndstooth pattern with a stretchy tailored knit. Sharp meets soft in all the right ways.
Ready to try it out for yourself? Scroll to see eight approachable ways you can start wearing the O’Hara blazer and other menswear-inspired separates right now.
1. The Secretly Stretchy Suit
While the O’Hara blazer and Horton pants are not new styles, the stretch houndstooth versions bring a brand-new meaning to “structure meets stretch.” These styles marry classic tailoring with a less traditional knit—giving you the visual structure you expect from a traditional suit plus an ultra-flexible feel you didn’t know was possible. Since you’re already swathed in pattern, opt for a solid underpinning like the Choe top in ivory and some simple jewelry like gold hoops and an everyday necklace. You definitely don’t need to stick to neutrals, though: Add a soft pop of color with the sky-blue Rowan flats or a dash of vibrant lipstick.
2. The Sophisticated Skirt Suit
Don’t write off shorter-length skirts as too girly or cute without giving them a chance. Styles like the Whitney skirt hit around the knee (depending on your height), providing an elongating effect while still being office-friendly. Dress up the houndstooth version of this skirt with the matching O’Hara blazer to create a full skirt suit, and balance out your leggy look with a high-coverage top like the Axam turtleneck and an over-the-knee boot like the Nina. Tie it all together with the Yuna earrings, which coordinate back to your camel underpinning. And there you have it: Your Whitney skirt is all grown up!
3. The Parisian Pairings
One of my favorite outfit formulas is an oversized blazer + skinny pants. It’s polished, foolproof, and a little bit Parisian. For an extra-easy version of this go-to combination, build an all-black base with styles like the Elizabeth turtleneck, Skinny Foster pants, and Zelda boots. Top off your stretchy, sleek ensemble with the boxy-in-the-best-way O’Hara blazer, and for the cherry on top, add a silk scarf and shiny hoops. Try tying the scarf over your turtleneck to really lean into the French vibe you have going on, or drape it over your shoulders for an effortless touch.
4. Widen Your Wardrobe
Some people are hesitant to pair a boyfriend blazer with wide-leg pants, imagining that combining two voluminous pieces will make them look bulky. In fact, relaxed silhouettes like the O’Hara blazer and Milo jeans do just the opposite: They elongate the figure and (literally) make room for confidence-boosting comfort. To keep the focus on your subtly statement-making silhouette, keep things streamlined with a polished T-shirt, classic studs, and pointed-toe flats.
5. Professional—with Personality
Big meeting coming up? Don’t leave your outfit planning until the last minute. Take your time crafting a distinctive, buttoned-up outfit that exudes both professionalism and personality. For example, start with your menswear-inspired blazer, and select coordinating—but not matching—suiting separates. The Darcy top in pearl plays off the ivory in your houndstooth jacket, while the Smith pants, Ginger pumps, and Claressa hoops introduce a warm richness into your palette.
6. Refresh Your Black Dress
If you’re looking for fresh ways to style a go-to black work dress, you can give it new legs with a few simple tweaks. For instance, toss a textured jacket over a straight silhouette like the Maaza dress, and slip on a bold belt for some extra waist definition. If you work in a business casual office, keep things Power Casual and no-fuss with leather sneakers and on-trend silver hoops.
7. Suit Up to Socialize
To some, suiting equates to workwear, but when styled right, it’s the perfect off-duty attire, too. The next time you go out to dinner, we encourage you to reframe your office-ready O’Hara blazer as an evening-ready layer with slightly sexy styles like a silk tank, vegan leather pants, and heeled boots. For an elegant finish, add a couple of gold necklaces plus a pair of sparkly studs, and ask for the dessert menu.
8. Winterize Your Whites
Wearing a dark-colored blazer is one of the easiest ways to put your light neutrals to work throughout the cold months. With the addition of the O’Hara blazer, your cream top and khaki pants instantly transform into chic winter essentials, while white sneakers and mixed-metal earrings pull together this tonal look.
