Coco Chanel started it all with designs inspired by her lover, Katharine Hepburn glamorized it during Hollywood’s “Golden Age,” and Diane Keaton immortalized it when she played the unforgettable Annie Hall. In short, menswear-inspired fashion has been around for quite a while—but year after year, we see it reinvented to suit the tastes of the modern woman.

Remember last year’s boyfriend jeans and boxy blazers? This year, we get sleeker, cleaner looks that balance loose fit with crisp tailoring. Here are a few things to consider when you’re attempting to pull off the new menswear look:

First, go with pants. This season’s retro redux has ushered in a range of wide-leg trousers and palazzo pants, so you won’t get bored with the same old denims.

Second, look for masculine touches—especially with dresses. Jacket collars, multiple buttons, and “shirty” details give you a cool, androgynous feel.

Third, layer. Toss a blazer over a polo, or a slip a buttondown under a jumpsuit. Aim for a three-piece outfit—and if that isn’t possible, strap on a belt!

Finally, wear boy shoes. Brogues, oxfords, and chunky booties are the gateway to a mannish look—even if you’re dressed in a flirty frock.

Below, you’ll find 20 outfit ideas to whet your appetite for menswear. Talk about tomboy-chic!

Like the outfits? Here’s where you can buy the pieces:

• Possibility, Faith Hope Love, and The Ramp are available at Crossings The Ramp in Shangri-La Plaza Mall, TriNoma, Glorietta, and Quezon Avenue.
• Plains & Prints is available at Alabang Town Center, Eastwood, Gateway, Market! Market!, Robinsons Galleria, Robinsons Metro East, Glorietta 5, Glorietta 3, Shangri-La Plaza Mall, SM Mall of Asia, SM Megamall, SM Southmall, SM Sucat, SM Marikina, Greenhills, TriNoma and Robinsons Department Store branches in Galleria and Shangri-La Plaza Mall, among other locations.
• Bayo is available at Shangri-La Plaza Mall, SM Mall of Asia, TriNoma, Alabang Town Center, Greenbelt 5, Power Plant Mall, Eastwood, SM Megamall, SM North EDSA,  Robinsons Galleria, Greenhills, Gateway, Podium, Glorietta 3, Market! Market!, Festival Mall, Robinsons Ermita, Sta. Lucia East, SM Fairview, Robinsons Metro East, SM Manila, SM Southmall, SM Sucat, SM Bicutan, SM Marikina, and SM Cebu, among other locations.
• Unarosa is available at Shangri-La Plaza, SM City The Block, SM Fairview, SM Megamall, Shoppesville Greenhills, Marquee Mall.
• Kisses & Co. is available at Robinsons Galleria, TriNoma, Alabang Town Center, SM North Edsa Annex, Robinsons Metro East, SM San Lazaro, Glorietta 3, and Tiendesitas.
• What A Girl Wants is available at Robinson’s Galleria and Ayala Center Cebu and online via wagw.multiply.com.
• Ensembles is available at Shangri-La Plaza Mall, Alabang Town Center, Festival Supermall, Eastwood, Glorietta 5, Robinsons Place Manila, Robinsons Galleria, SM Bicutan, SM Megamall, and TriNoma.
• CMG is available at Robinsons Galleria, Robinsons Midtown, Power Plant Mall, Shangri-La Plaza Mall, Alabang Town Center, Gateway, Glorietta, Greenhills, SM Mall of Asia, SM Megamall, SM North Edsa, and TriNoma, among others.
• Schu is available at Shangri-La Plaza Mall, Robinsons Galleria, Power Plant Mall, Glorietta 3, SM Mall of Asia, TriNoma, and Ayala Cebu, among others.
• VNC is available at Alabang Town Center, Eastwood Mall, Glorietta 3, Shangri-La Plaza Mall, SM Mall of Asia, SM Megamall, Robinsons Place Ermita, and TriNoma.
• So! Fab is available at Glorietta 5, Market! Market!, Shangri-La Plaza Mall, The Ramp Crossings in Shangri-La Plaza Mall, Alimall Cubao, Greenhills Shoppesville, SM Clark, SM Manila, SM North Edsa The Block, SM Southmall, Ayala Cebu, SM Cebu, among others.
• Susto, Androgyny, Cocobelle, Lemon, Made U Look, Mobi & Red, Love Jane, Beltza, and Cole Vintage are available at 50th Avenue in Robinsons Galleria.

For more FN style guides, check out these galleries:

• Color Block: 20 Ways to Wear Brights
• A Girl's Best Friend: 20 Ways to Wear the LBD
• What to Wear to Work: 18 Outfits for Corporate, Creative, and Casual Dress

(Photos by Datu Angeles. Styling by Stephanie Castillo. Assisted by Pat Dayacap.)

Add us on Facebook and Twitter!