Ever since Marlene Dietrich shocked the world by assuming a tuxedo in the 1930 film
Morocco, women have been merrily appropriating men's attire to great effects. The once taboo practice of sporting a fellow's threads is at an all-time high this fall, thanks to designer and celebrity support of
blazers,
fancy pants,
briefcases, and more! Considering our own preference for looking like we've raided a guy's closet (usually via Jenni Kayne's
Boyfriend Shirt

($355), one of our current wardrobe favorites), we very much enjoyed determining the perfect pieces that will allow you to mix a little masculinity into your own outfits. We know your budgets are probably in a bare bones state right now,so we sleuthed out the best in boyswear for $100 or less.
If you're in need of a modern-day muse who masters androgynous style, look no further than
Irina Lazareanu, as she fearlessly and frequently accomplishes masculine get-ups with astonishing grace. While Lazareanu's tweed blazer and baggy pant combos are highly admirable, we're not implying that you have to dress like a boy from head-to-toe in order to incorporate menswear into your wardrobe. Rather, try mixing and matching some of the above items with feminine garments to find a balance that suits you.
Alexander Wang did this brilliantly when he combined slouchy blazers, mesh skirts, and oversized button-up shirts in his fall collection. Some of our other favorite menswear-inspired moments from fall include Isabel Marant's oversized blazers (belted at the waist for a ladylike touch), the
Twill Karate Pants
($775) from Proenza Schouler, and the
Tweed Newsboy Caps ($175) shown at Dolce & Gabbana. Read on, dear readers, for your own personal ticket to the boys' club! —Jessica Amento
1.
EP Caliber Vintage Aviator Sunglasses ($10)
These Tom Ford-reminiscent shades will automatically accent the masculine elements in any outfit. We picture someone with an effortlessly cool essence—like Michelle Williams—wearing them.
2.
Urban Renewal Vintage Lady's Blazer ($48)
If you plan on practicing a menswear look at anytime, a blazer is the single most important piece to have on hand. We are especially taken with vintage options, like this one, courtesy of Urban Outfitters, for their great price and cut. Wear them with a frilly blouse for a boy-meets-girl effect.
3.
Timex Dress Watch ($65)
Even if you aren't punctual, you can fake it with this oversized watch. It reminds us of something we would take from our grandpa's closet. Another reason to love it: the chunky band will make even hefty wrists look bird-like!
4.
Liz Clairborne Vintage Croco Organizer
($74)
As regular readers know, we love our briefcase-style bags right now, and this mock croc version is simply perfect. You'll blend right in at wall street with it!
5.
Topshop Herringbone Tail Waistcoat ($65)
You can wear this vest with a rugged tee and boyfriend jeans during the day and then adapt it to an evening look by throwing it on over a floral dress, black tights, and over-the-knee boots.
6.
H&M Trousers ($35)
These baggy pants remind us of the slouchy slacks seen on Proenza Schouler's fall runway. Wear them with some unexpected platform heels or perhaps the
Balmain-inspired fringe boots, and a tucked-in tee or other fitted top.
7.
Charlotte Russe
Herringbone Tweed Fedora
($28)
Throwing on a
hat will simply and effectively put a boyish spin on any look! The neutral color of this fedora makes it an easy add-on to any outfit.
8.
Brooklyn Industries Thayer Skirt ($78)
We love that the feminine shape of this skirt is off-set by its masculine wool-blend fabric. Wear it with an oversized blazer, patterned tights, and lace-up patent heels.
9.
Steve Madden
Oxxie Flats
($70)
As a cousin to the loafers we're currently fond of, we are equally besotted with these patent lace-up shoes. Look to
Alexa Chung—the flats queen—for inspiration on wearing them with feminine ensembles.
10.
Ralph Lauren Faux Croc Skinny Belt ($42)
Take a cue from Isabel Marant by cinching this skinny belt over a blazer. Also, note that you can easily mix and match this with the rest of the accessories in today's story.
11.
Les Prairies De Paris Stockette ($48)
We admit that we have stolen a few socks like these from our boyfriends over the years, but it never hurts to add another set to our stockpile! For some juxtaposition below your ankles, try wearing this pair scrunched up under some platform heels.
16 post(s)
Love the socks!!!
Posted by: L | 2008-11-21 15:57:57
this post is great! i love that it's great stuff that we will want and AFFORDABLE! great work whowhatwear! those of us with a extremely smaller budget than celebrities appreciate it so much. keep it up please!
Posted by: m | 2008-11-01 23:09:08
the liz claiborne purse is absolutely delicious!
Posted by: carmen | 2008-11-01 23:06:51
ugh i absolutely adore the jenni kayne look...if i could leave the house each day looking like that, well, i would be truly happy. ach well.
Posted by: sarah | 2008-11-01 01:07:25
great post!! loving all the selections!!
Posted by: crista | 2008-10-29 20:32:45
Well done, girls! The Annie Hall look is always my fave when transitioning into Fall. Too bad is not cool enough where I am to pull this off yet. I can't wait to wear my tweed trousers. Thank you for this inspirational post.
Posted by: Annie Hall | 2008-10-29 16:59:47
i love the thayer skirt, watch and liz claiborne bag! so cute
Posted by: kisskiss | 2008-10-29 14:25:42
i love menswear style but im not completely satisfied with this selection.
Posted by: la de da | 2008-10-29 14:23:01
This is a great post! Everything looks FABULOUS and is totally affordable. I especially love the bag, the skirt and the belt.
Posted by: ebay fashion ad | 2008-10-29 10:30:42
Very well done post. A great breakdown of the menswear pieces and equally great suggestions.
Posted by: stephanie | 2008-10-29 08:29:15
I love the topshop waistcoat, Thayer skirt and I want that watch. Good post but im sure you could have found some socks for way under $48.
Posted by: Camilla | 2008-10-29 06:43:20
ha ha. 48 dollar socks. ha ha ha ha.
Posted by: haha | 2008-10-29 01:06:59
it says brooklyn industries there..... but yes, love these selections!!
Posted by: lovesgemma | 2008-10-29 00:38:48
I like this post a lot - excellent selection. One thing though - the name of the skirt is Thayer but it should be labeled by its brand name, Brooklyn Industries. I recall that they make all of their items in house. xx rubyfuerza.com
Posted by: Ruby Fuerza | 2008-10-29 00:15:28
one of my favorite posts ever!!!! honestly, these pieces are all great. it doesn't look like you just chose them because they were under $100, but the fact that they are makes them even better!!!! great job who what wear girls!
Posted by: fashionista | 2008-10-29 00:15:20
I love mens wear style inspired fashion for women. Something about grandpa pants, a collard shirt, brogues and a fedora on a woman that I love. I love vests with a little t.shirt it totally makes an outfit look chic and sophisticated and adds a point of difference. I will always love flat man style shoes with socks too..totally cool. Love this post. ta
Posted by: g says | 2008-10-29 00:12:32