I’ve recently made a few more fantastic purchases: a couple Tommy Hilfiger boy’s polos, and a Ben Sherman backpack on sale at ASOS. I felt that my wardrobe was lacking in bright colors, so I took the plunge and got some orange to go with all the navy I already had. Plus, how can I be a true Prepster without bright colors? All I need now is a lakeside house in New Hampshire and some boats… 

Polo: Tommy Hilfiger Boys
Watch: 666 Barcelona
Belt: Abercrombie & Fitch Preppy Braided Belt
Shorts: Old Navy Women’s Perfect Khaki Bermudas
Boat Shoes: Sebago Docksides
Backpack: Plectrum Canvas Backpack by Ben Sherman

Anonymous asked: Hey I just bought some really cool shorts from Gap. They’re denim but are a sort of khaki/army green color. I believe the tag called it ash. They fit about to my knee and I was just wondering if you had any tips on what would be super awesome to wear them with.

Mandy says: You can wear these shorts with just about ANYTHING, except for the same color. I think off-color denim shorts look really good with a white button down, but I could definitely see this outfit working with a patterned or textured shirt (like madras, gingham, linen, or chambray). I prefer to dress up shorts with oxfords/brogues/loafers, but I also love shorts with low-top Converse All-Stars. 

The Fourth of July is coming up, meaning it’s time to celebrate the values America may or may not be built on. But I mean, if we’re going to create change, we may as well do it in style. People will be way more likely to listen to you when you’re wearing your new pair of sexy red glasses.

Super Clear Frame Lenses in Red, Available At Revolve Clothing for $138

Selected Oxford Shirt, available at ASOS for $58.00

Royal Blue Leather Sebago Docksides, on sale at My Wardrobe for $90.75

Deep Blue Wonder Dress, available at Modcloth for $107.99

Blue and White Stripe Snapback, available at Topman for $28


Jessica Quirk showing off her hand-painted stars and stripes shorts. Learn how she did it here. (Source: What I wore)

Tennis Skirt, available in in Red, White, and Blue at American Apparel, for $54

All the queers have been writing in to tell us about how well Levi’s mens skinny pants fit. 511™ Skinny Commuter Pants, on sale at Levi for $53.90

Converse All Star Slim Plimsolls, available at ASOS for $66.28

Blue Slim Chino Belt, available at Topman for $24 (Also comes in red)

Um, pink menswear with contrast collars? Color paneled Boat shoes? If your heart hasn’t started pounding already, I don’t know what else to say.

Pink dress shirt: Brooks Brothers, I can’t find that exact shirt on the Brooks Brothers’ website, but they also allow you to Create Your Own.
Glasses: Ray-Ban 
Black Pants: Next Generation (from Burma, very smooth texture)
Boat Shoes: Sebago Spinnaker
White Watch: French Connection United Kingdom (FCUK)
Canvas Tote bag: Ben Sherman 

Finding smaller masculine styles for female bodied feet can be a tough one (as evidenced back in this post) but with your help and my own endless research I’ve found lots of great brands that have a selection of masculine shoes for women. Here are a few of my favorite dandy styles that will fit us smaller-footed folks:

JAZIE, available at Steve Madden for $89.95

Bass “Walk and Talk” flat, available at Modcloth for $68.99 (See me wearing mine here!)



Halifax Strap, on sale at Sebago for $62.99




LunarGrand Wingtip, available at Cole Haan for $278



Comme Des Garçons, available at farfetch.com for $582

Marksy Leather Brogue with Contrast Sole, available at ASOS for $58.17

Dolly Blue and White Saddled O’s, available at Rupert Sanderson for $535

Mimi’s back for part 3 with some more excellent combos. Checks, polka dots, stripes, blazers, epaulettes… damn girl. She’s knows how to handle pattern and detail.

Button-up: J. Crew Gingham Perfect Shirt
Cardigan: Forever 21
Tie: Thrifted 

Pants: Gap (Corduroys) 
Shirt: H&M
Blazer: Not sure, Nordstrom Rack
Shoes: Sebago
Watch: Kenneth Cole, Nordstrom Rack
Band: NATO

silvercake asked: okay i own a pair of sebago docksides that i love, but they're awful to wear. i end up with giant blisters & raw spots everywhere, but especially on my heels where they rub the worst. do they just not work for me? is there some magic trick to breaking them in? did i miss the memo on invisible socks?

You did miss the memo on invisible socks ;) Hope that helps. I can’t stand wearing shoes without socks. You can also try a sole insert to raise your ankle and see if that makes a difference. I wouldn’t wear my Sebago Docksides on a hike or anything, because they eventually start to rub against my heel too. It may just be that docksides will never float your boat, in which case I’m sorry that your lovely shoes aren’t working out.

Anonymous asked: Help! I need ideas for my summer swag!

Straw hat, available at H&M for $9.95

Jane Aviator Glasses, available at Alloy for $10.90

Plaid Woven boy’s shirt, available at Tommy Hilfger for $29.00

Boys Jersey Ringer Tee, available at Old Navy for $6.50

AE Classic Length Plaid Short, available at American Eagle for $34.99

Ribbed webbing belt, available at the Gap for $19.95

Sebago Docksides, available at Infinity Shoes for $79.95

Check out the summer tag for more ideas

In my world, less is more. And when you have jeans and a T-shirt that fit well, you don’t need any more. Wear more the next day. Your outfits will string together in people’s heads like a flip book.

Glasses: Adrienne Vittadini
Shirt: Epic Threads (Macy’s boys 8-20 department)
Belt: Express (men’s)
Jeans: Abercrombie & Fitch, “The Erin Skinny”
Shoes: Sebago Docksides

Related Posts: The Power of Simplicity

I got these shoes for my birthday. I recommend buying real boating shoes even if you never go boating because these babies will last forever. It’s about time I step up my game; I’m turning 23!

Sweater: Ralph Lauren Polo  (Macy’s boys 8-12 department.)
Shirt: Gap “The Perfect Shirt”
Watch: Tikkr 
Belt: Bought at Sam’s Outdoor Outfitters
Shorts: Old Navy “Women’s Perfect Khaki Bermudas”
Shoes: Sebago Docksides

Related Posts: Ashley Yielding: The Southern Androgynous Internet Sensation