As I’m sure most of you remember, Jenilee was the site’s first photographer/intern.

Not only is she a talented photographer with equal parts cute and smart, she’s also one of the most stylish girls I’ve ever met. The best part is, she loves menswear and pulls it off better than most men! See her first feature here.

We caught up with Jeni again, this time down in her hometown of Nashville Tennessee for another series of menswear-inspired looks.

1. His Look, Better Than Him

“This is one of my favorite everyday outfits. I love how comfortable and easy it is.”

Bonus Tip: “Makeup and hair are easy areas to add a womanly touch – and remember good posture helps you look less like a man and more like a dainty woman.”

Bonus Tip II: An earthy color palette looks good on just about any skin tone. I’ve actually worn an outfit almost identical to this one.

Shirt (men’s) and pants by J.Crew. Watch by Timex. Desert boots by Clarks (a gift from Dan). 

Bonus Tip: No matter your sex, you should know a good tailor.

Dress and boyfriend blazer (tailored) by Jcrew. Heels by Banana Republic. Boyfriend watch by Fossil. Vintage clutch. Locket by Tiffany’s.

3.  Sailor Girl

“Footwear might be my favorite thing to steal from a man’s wardrobe (that and button-downs)… Summer means breaking out my white bucks. They’re such a staple men’s item but look great paired with a cropped pant and french-siliouhetted top too.”

Bonus Tip: Navy and white, never fails. Keep it simple, keep it sexy.

Shirt by J.Crew. Pants by Paper Boy. Bucks by Cole Hann. 

4. Shirt & Skirt

“Combining a cute, fimine piece with something more masculine is a great subtle way to introduce menswear into an outfit. This pink and white striped oxford is a versatile men’s shirt (that I had tailored). I can wear it casually with shorts and my Clarks, or even as a comfy lay-around-the-house shirt.”

Bonus Tip: There can be a fine line between a purse and a briefcase. With a menswear-inspired look, it makes sense to flirt with that line.

Shirt (men’s) and skirt by J.Crew. Shoes by Banana Republic. Purse by Dooney and Bourke. Glasses by Warby Parker. 

5. Yeah, Boy

“I’m no stranger to the men’s side of the store, or the boys department either! …I realize this is only an option for a small framed woman like myself, but if you can fit, take advantage! Kid’s clothing is normally cheaper and boys sweaters and jackets tend to have a nice crop.”

Bonus Tip: For small-framed men, the same rules apply. Don’t be afraid to take a peek on the children’s side. There is small differences in fit from a men’s XS and a boy’s XL anyway.

Bonus Tip II: Classics – like these Weejun loafers (or the oxford shirt and blue blazer from above) – can work on almost anybody.

Boy’s Fishermen’s Sweater  by L.L.Bean. Shorts by J.Crew. Loafers by Bass. 

6. Show Some Frame

“I love wearing items that make me feel like a woman but that doesn’t mean I reach for frills and lace. Wearing a pant that shows off your curves and looks great with heels can do the trick.”

Bonus Tip: Pocket square in shirt.

Bonus Tip II: Bowtie as pocket square.

Shirt by Gap. Pants by J.Crew. Bow Tie (as pocket square) from The Tie Bar. 

Thanks, as always, for reading – and special thanks to Jenilee for participating.

Yours in style,

SB

Photography by Alex Crawford.