Fashionated: Tomboy Style
Androgyny is all the rage on the runways, but the look has more humble beginnings.
For those who like a masculine edge to their personal look, the Tomboy style is the androgyny-friendly look that blends classic shapes with traditionally male details, resulting in a chic, wearable, style for any occasion.
Tomboy Day Looks
Traditionally, tomboys prefer pants to dresses or skirts, and that is great for day wear.
To keep looking sophisticated and not sloppy, opt for tailored, well fitting pants or jeans. A slim, dark skinny jean, can accentuate most figures, and provides a great tailored base for our tomboy look.
For weekend wear, a “boyfriend” jean (slightly baggy with rolled cuffs) is one of my favorite options, often topped with a graphic tee and slightly shrunken blazer, and flats.
For our more alternative-tomboys, skirts can still be great. Pair a knit midi a more masculine graphic tee and a pair of sporty flats, and you are good to go. Leggings can be another option that gives a feminine dash to otherwise masculine options.
A classic button-down, fitted or loose, pairs great with all the above options. Add a pair of bright or sporty flats, a blazer or other structured jacket, and metal-detailed jewelry to your liking.
A chunky chain, gold or silver wide-faced watch, and simple studs or hoops, pulls your look together while still feeling comfortable.
Tweed, elbow patches, shrunken shape...this is a blazer of tomboy dreams! Dress it up with a vest and wide trousers, dress it down in skinny jeans and a tshirt, this blazer is amazing. Pair it with metallic brogues and just call it a day!
Diane Keaton, Tomboy Icon
Work Appropriate Tomboys
For work, jeans may not be appropriate for everyone's vocation, so trade them in for either a slim pair of black pants (preferably cropped), or a wide-legged trouser. Think Katherine Hepburn in her down time...easy elegance that doesn't rely on feminine lures.
Pull inspiration from classic menswear: checks, plaids, woolens and flannels, are all sophisticated variations on the same tailored look.
Blazers, blazers, blazers: Can I say enough about blazers? Don't even consider incorporating a tomboy style into your day to day if you do not own at least one blazer. This epitome of classic staples takes all of its moves from the boys' club, and it is one of the great power pieces of a woman's wardrobe. Buy one, buy six, just make sure that they fit well in the sleeves and the waist.
Or, take a cue from Diane Keaton in Woody Allen's "Annie Hall." The wide-legged pants, cropped vest, and men's style brogues, give her a commanding, yet alluring, air. She is chic, but powerful, a force to be reckoned with.
Katherine Hepburn, Queen of Pants
Great metallic oxford from Cole Haan. Perfect for the tomboy look!
More Tomboy Work Looks
Tops for work should follow the opposite line of the pants. For fitted crops, a slightly looser top (but not baggy!) will be most flattering, and again I advocate a blazer. With the slim line of fitted pants, more layers on top can help to balance even the curviest frame, or add curves to those who are naturally lean. With wide trousers, most anything goes. A slim tank with a cardigan can be very chic, but avoid too many embellishments. A soft blouse can be romantic and strong at once, and even a chunky pullover can make the grade. Shoes are simple, often referencing male styles, like a brogue or wing tip.
Tomboys and Evening Wear
For evening, the tomboy look is one of my all-time favorites.
Is there anything sexier than a woman in a well-cut tuxedo?
Palazzo pants are more common, yet the softness can feel contradictory to the structured tomboy style.
But a well-fitted black pant, especially with a satin tuxedo stripe, can bring instant allure and charm. Topped with a silk tank in almost any color, and a sharp pair of shoes (wedges and kitten heels are what I suggest for the heel-experienced, but a well-polished lady's wing tip can also be very chic), the lady-tux is a winner.
A tux jacket can totally be used as well, but only if your blacks match very well. (A mix of faded blacks can kill an outfit in an instant).
To up the sex appeal of the otherwise androgynous look, skip the silk tank and use fashion tape to hold your jacket in place.
Marlene Dietrich, Rocking the Accessories
A note on tomboy accessories:
Fedoras are tricky. Like, 1 in 17 people can wear a one and not look like they are trying too hard. And that is key! Great style is all about looking chic without effort, or at least apparent effort. So watch out for hats.
Accessories that can make a look:
- suspenders (narrow, simple, consider leather as well)
- pocket watch and fob (chic detail, classic )
- ties (narrow and Italian-inspired are best)
- a fantastic watch ( I am a fan of an oversized face and chunky metal)
I love Kate Spade watches, and the Gramercy collection has a great androgynous feel to them Weighty in a classic metal style, this watch commands a hint of attention. Of course, you can always go with a men's watch, but I like the masculine/feminine styling of this!
Tomboy Style Reminders
- Structure is necessary.
- Be careful with accessories, but still use them!
- Borrow masculine details from the boys.
- Never underestimate the power of a woman in a tuxedo.
- Aim for androgynous chic, not sloppy.