How to Dress Like a Tomboy With Long and Short Hair

Even if you have long hair, there are days when you want to take a break from wearing feminine dresses and get comfortable in pants. If you are having one of those days, you might want to learn a thing or two about what you need to build a menswear-for-womenswear-friendly wardrobe.

The key to mastering the tomboy style is finding basic and classic pieces that fit with the more modern ones in your closet. Think button-down tops and pinstripe blazers worn with sporty footwear. You don’t have to shop in the menswear section, though. The following female-approved pieces will help you create ensembles that will get you in touch with your masculine side, regardless of your hairstyle or the length of your hair.

1. Pinstripe blazer

A pinstripe blazer is a classic piece that you can get a lot of wear from. Sarah’s approach is to wear a pinstripe blazer over an untucked button-down shirt and slouchy black pants. To get that street-style vibe, get a pair of sneakers instead of formal oxfords.

Sarah wearing a pinstripe blazer over an untucked button-down shirt and slouchy black pantsSarah wearing a pinstripe blazer over an untucked button-down shirt and slouchy black pants

2. Tartan tapered pants

Since the tartan print never goes out of style and tapered pants work with different separates, tartan tapered pants are worth hunting for. Willabelle’s pair of grid-patterned pants is a sterling example. Worn with a double-breasted blazer, this suit outfit is chic for both work and play.

Willabelle with long hair wearing tomboy style tartan tapered pantsWillabelle with long hair wearing tomboy style tartan tapered pants

3. Drawstring pants

Nothing screams comfort quite like drawstring pants! Balance out the sporty and masculine vibe of these pants by wearing them with either edgy or feminine pieces. Alexandra chose a leather jacket and a pair of pumps to get the best of both worlds.

Alexandra with medium length hair in a leather jacket and masculine drawstring pantsAlexandra with medium length hair in a leather jacket and masculine drawstring pants

4. Suspender pants

You can wear suspenders with your denim jeans rolled up at the hem. Rachel-Marie amped up the menswear vibe with a button-down shirt, a trench coat, and lace-up boots.

Rachel-Marie amped up the menswear vibe with a button-down shirt, a trench coat, and lace-up bootsRachel-Marie amped up the menswear vibe with a button-down shirt, a trench coat, and lace-up boots

5. Loose button-down

Wear a loose button-down shirt under a loose sweater and over baggy pants like what Gina did here. Cap off the look with lace-up boots. Her blog is unfortunately no longer available online.

Gina wearing a loose button-down shirt under a loose sweater and over baggy pantsGina wearing a loose button-down shirt under a loose sweater and over baggy pants

6. Old-School Vest

Layer up your sweater and jeans look with a vest! This old-school trick not only gives more warmth but also keeps your comfortable look interesting! Like the long-haired Misia, finish the outfit off with ankle boots. Her blog is unfortunately no longer available online.

Misia perfected the tomboy look by styling jeans with a sweater and a vestMisia perfected the tomboy look by styling jeans with a sweater and a vest

7. Boxy sweater

Boxy sweaters and tapered cropped pants? The combination never gets old. Arm yourself with boxy sweaters peppered with interesting prints and wordings on them like Estefania. Her blog is no longer available online.

Estefania with long hair in a boxy sweater and tapered cropped pantsEstefania with long hair in a boxy sweater and tapered cropped pants

8. Denim jacket

If you aren’t in the mood for fitted denim pants, get your denim fix through your jacket instead. Denim jackets work well with slouchy printed pants, as Lucia showed us with her chic outfit. Her fashion blog is no longer available online.

Lucia wearing a tomboy denim jacket with slouchy printed pantsLucia wearing a tomboy denim jacket with slouchy printed pants

We also looked around for more pants you can use to build your menswear-inspired wardrobe.

Issey Miyake Cropped Trousers, $610

Issey Miyake Cropped Trousers

Saint Laurent Tailored Trousers, $827.35

Saint Laurent Tailored Trousers

Fendi Striped Tapered Trousers, $1,297.34

Fendi Striped Tapered Trouser

Jil Sander Roland Narrow Cargo Trousers, $607.11

Jil Sander Roland Narrow Cargo Trouser

Christopher Kane Washed Denim Jeans, $504.70

Christopher Kane Washed Denim Jeans

Brunello Cucinelli Straight-Leg Trousers, $707.64

Brunello Cucinelli Straight Leg Trousers

Now, style these pants up the way the above bloggers did, and you won’t have to worry about crossing the line between menswear and womenswear far too much!

DO YOU LOVE SHOES? Win free shoes, organize your shoe closet, see the latest styles + more

Speak Your Mind

*

16 + 12 =

© Copyright Your Next Jeans 2010 - 2018 | Back to Top