LAURA | SAN FRANCISCO| FASHION BLOGGER | ON THE RACKS

Shirt:Zara|Skirt:Seneca Rising|Belt:Zara|Cage Booties:Jeffrey Campbell|Necklace:So Good

As far as I'm concerned, you can never go wrong with a classic button down. To look less middle-management and more top of the line, opt for a flirty skirt and heels like Laura.

MARLA | JOGJAKARTA | STUDENT |VERSICLE

Blazer:Thrifted|Blouse:Thrifted|Leggings:Topshop |Booties:Forever 21|Bag:Screamous (local store in Jogjakarta) |Sunglasses:Forever21

Marla proves that less is more with a subdued color palette and strong, clean lines.

MARLA | JOGJAKARTA | STUDENT |VERSICLE

Blazer:Thrifted|Blouse w. Silk Scarf:Thrifted|Corduroy Shorts:Oink! (local store in Jogjakarta) |Wedges:Topshop|Bag:Yves Saint Laurent

Marla, a blogger and student based out of Jogjakarta, Indonesia and featured as a Girl of the Week on TeenVogue.com, is taking the prep school look to the next level. Penny loafers or saddle oxfords would have been too literal, so she definitely gets high marks for the multi-colored wedges. See more of this outfit on her blog, Versicle.

RYAN | GREENPOINT | ODIN

Shirt:Evidence of Evolution|Tee:American Apparel|Jeans:Earl|Shoes:Comme des Garçons|Watch:Casio

Ryan's button down does double-duty as a jacket on a less than hot, not quite cold day.

PAVAN | NEW YORK | SURGEON

Shirt:APC|Jeans:APC|Shoes:Salvatore Ferragamo|Watch:Timex

The soiled streets of the city are a lot cleaner with Dr. P on his rounds. The king of crisp and casual strikes another understated sartorial chord.

RYAN | GREENPOINT | ODIN

Shirt:Martin Margiela|Jeans:Vintage|Sneakers:Converse|Watch:Casio

Often, looking sharp lies within simplicity. A shirt and jeans is all it takes sometimes.

RYAN | GREENPOINT | ODIN

Shirt:Shades of Greige|Jeans:Jean-Paul Gaultier|Sneakers:Converse|Watch:Casio

For some, warmer days equal a cooler palette. Keep out the heat with light and loose fabrics.

SARAH | NEW YORK | MERCHANDISE ASSISTANT

Shirt:J. Crew|Shorts:American Apparel|Bag:Chanel|Wedges:Chloé|Sunglasses:Oliver Peoples

Just because you're on vacation doesn't mean that your style has to be. SYS mainstay Sarah is proof positive that you don't have to sacrifice looking sharp for feeling relaxed.

SCOTT| BAY RIDGE | SALES ASSOCIATE | HOLD A DESERT

Work Shirt:Woolrich Woolen Mills|Shirt:Band of Outsiders|Shorts:Rag + Bone|Desert Boots:Clarks

Scott neutralizes his palette for the warmer months with cooler colors.

GRADY | WILLIAMSBURG | HEAD WRITER FOR GRUMPY FILMS

Suit:Umii by 45 rpm|Shirt:Oliver Spencer|Belt:45 rpm|Oxfords:Florsheim by Duckie Brown|Sunglasses: Vintage

Whether Easter for you is about Jesus or that elusive bunny, you've got to look sharp. Grady's seersucker suit celebrates the season with a nod towards tradition.

JEREMY | BUSHWICK | PSYCHIC | THE 48HRS

Shirt:Edward|Pants:A-OK|Shoes:Rachel Comey|Belt:Oliver Spencer

Leave the exposed chest hair and gold chains to Tony Manero. Take the buttoned up look literally for a more modern approach.

PAVAN | NEW YORK | SURGEON

Shirt:J. Crew|Shorts:American Apparel|Trainers:Superga

A weekend at the lake house doesn't mean you have to dress like a scrub...even if you wear one to work. Here Dr. P shows us how to be comfortable and crisp.

SARAH | NEW YORK | MERCHANDISE ASSISTANT

Jacket:Elizabeth and James|Cardigan:Club Monaco| Shirt:J. Crew|Boots:Topshop|Bag:Miu Miu|Sunglasses:Oliver Peoples

Lovely layers on one of those temperamental, in between days. Remember to stay away from pieces that are too thick—creates too much bulk. Save that sleeping bag of a coat for days when it’s -5 °F.