Cure a case of cabin fever with the items below (from left):

1. Kensie “Nomad” shawl cardigan ($78; Nordstrom)
2. Chunky knit scarf ($60; Topshop)
3. K.Amato wood and gold leaf ring ($30. K.Amato; 1229 W Diversey Avenue)
4. Steven Alan plaid dress ($248)
5. “Everest Overnight” bag ($395; Rag & Bone)
6. Minnetonka fringe moccasins ($88; J.Crew)
7. Hue tweed cable-knit socks ($14; Bare Necessities)
8. Patterned beret ($36; Penelope’s; 1913 W Division Street)
9. Staring at Stars faux fur vest ($98; Urban Outfitters)

By Leslie Garry

Images courtesy of Kensie, Topshop, K.Amato, Steven Alan, Rag & Bone, J.Crew, Penelope’s and Urban Outfitters

The coupling of these two unlikely fabrics creates a fashion juxtaposition that’s hard to resist. Soft, supple leathers meet delicate lace for a combination that makes a downtown ensemble that’s distinctly ladylike too. To keep the look current, stick with black leather and white or cream laces. Looking to sharpen your edge? Pair with a strong red lip and layered silver chains, nothing is chicer.

Channel your inner vamp with the below items (clockwise from upper left):

1. CCSkye “Nika Lace Leather Pouchette” ($308; shopbop.com). From the shape to the print, this on-trend bag is perfectly girly.
2. Lace tee ($110; J. Crew). A dressed up fabric in a laid-back cut.  
3. Christian Louboutin “Lace Crepe-de-Chine” pump ($725; Bergdorf Goodman). The ultimate feminine pump: sexy and ladylike.
4. Diane von Furstenberg tiered leather skirt ($625; Cusp). Flirty and romantic with an edge.
5. Dolce Vita leather lace-up boots ($212; Lori’s Shoes; 824 W Armitage Avenue). This boot’s laces give it a throwback vibe, but the buckle and shape make it au courant.
6. Leather biker jacket ($310; Topshop) A tough jacket to contrast delicate laces.

By Leslie Garry

Images courtesy of shopbop.com, J.Crew, Bergdorf Goodman, Cusp, Lori’s Shoes and Topshop

These pieces are on my fall “keep list” because they take just a little adjusting to make them fit for next season. After all, isn’t summer worth holding onto as long as possible here in Chicago?

1. Theory “Iselin” leather shorts ($315; Bloomingdales). Leather shorts were big for summer, and lucky for us the heavy fabric can be easily paired with colored and textured tights for crisp nights.
2. Plastic Island tunic ($127; plasticisland.com). What I paired with denim cutoffs and flip flops for summer is now the ideal knit with leggings and combat boots.
3. Jeffrey Campbell “Mary Roks” ($120; Lori’s Shoes; 824 W Armitage Avenue). Open-toed wedges aren’t just for warm weather. Rock these with tights to keep them relevant.
4. Solid ripstop field jacket ($98; J.Crew). Use this lightweight jacket as a layering piece over a chunky sweater.
5. Frozen Flash necklace ($58; Anthropologie). Lucite accessories aren’t only summer staples; extend your purchase by incorporating them into fall’s day and night looks.
6. Alice + Olivia painted floral print top ($187; Cusp). A lightweight floral tank with a vibrant fall palette—a feminine accompaniment with a leather bomber.

By Leslie Garry

Images courtesy of Bloomingdales, plasticisland.com, Lori’s Shoes, J.Crew, Anthropologie and Cusp

When hunting for your new collar-wear, seek out pieces that incorporate mixed metals, twisted chains and faceted crystals. Be bold with your selection because the most stand-out designs are dazzling yet tough, and shamelessly costume-inspired. By fusing tough grunge and glitzy bling, the right statement necklace is perfectly rebellious and glamorous, melding eye-catching details like daggers, tangles, rhinestones and heavy metal.

Try pairing one of these necklaces with an innocent floral frock for an edgy look or update an old LBD with some lust-worthy sparkle.

1. FENTON/FALLON for J.Crew rhinestone “Jaws” necklace ($135; J.Crew).
2. Lee Angel chunky bead and crystal necklace ($385; Intermix)
3. “Twisted Metal and Crystals” necklace ($98; Madewell)
4. Fallon “Victoria Ball Swag” necklace ($275; Barneys CO-OP)
5. ”Flat Spikes on Chain” necklace ($32; Topshop) 
6. Fool’s gold choker necklace ($250; Luv Aj)

*DYI Tip: Can’t find the perfect statement necklace? Make your own by twisting individual necklaces. Mix, match and layer each strand until it’s just right.

By Leslie Garry

Images courtesy of J.Crew, Intermix, Madewell, Barneys CO-OP, Topshop and Luv Aj

Denim vests are both a layering piece and a jolt of excitement to a mundane outfit. Taking inspiration from motorcycle gangs, 80’s rock bands, and New Kids On The Block, this season’s denim vests toughen up girly dresses and add dimension to basic tanks and tees. Much like the leather jacket, this topper complements almost any outfit and looks especially fresh when paired with stripes, flowered prints and high-waisted pants. Boxy cuts with cut-off sleeves exude a badass vibe, but lighter, fitted vests are more feminine and conservative when buttoned, or, in some cases, worn solo.

Though my treasured acid-washed vest remained intact after all these years (minus the N.K.O.T.B buttons, of course), there are hundreds of new styles to choose from this season in case you mistakenly discarded yours.  

Clockwise from upper left:

1. Studded Denim Vest ($248; Juicy Couture). Both chic and tough to contrast a feminine dress.
2. Denim “Waterfall Waistcoat” ($80; Topshop). A modern cut in a light fabric is summer-ready.
3. “Leah” Vest ($180; True Religion). White and ragged feels fresh but edgy.
4. Colcci denim vest ($53; New’d, 1917 W Division Street). For a less boxy look, this preppy style offsets a loose or wide leg pant.
5. Distressed vest ($40; American Eagle Outfitters). A fitted, medium-hued style is figure-flattering and timeless.
6. Denim vest ($88; J.Crew). With a light wash and a classic cut, you can’t go wrong.

By Maia McGinley

Images courtesy of Juicy Couture, Topshop, True Religion, J.Crew, American Eagle Outfitters, and New’d

While yachting might be out of the budget, keep this season’s nautical look afloat by taking it to the street. The summer’s maritime-inspired pieces create a fresh approach to sea-worthy style and prove to be a wise investment, as elements of this timeless trend return season after season. Set sail with a mix of patriotic colors, clean lines, and metallic touches for added flare—a suitable combo for the office, summer strolls, and, of course, a yacht.

Clockwise from upper left:

1. Cape-stripe swimsuit ($112; J. Crew). The essential suit for summer afternoons on land or sea. Pair with a crisp white oxford for a chic cover-up.
2. Platinum Sperry Top-sider boat shoe ($85; Nordstrom). A metallic edge on a classic style.
3. Rag & Bone red skinny jean ($175; Barneys). A pop of primary color adds a vibrant flare to a sleek cut.
4. Twisted chain collar necklace ($38; Lori’s Shoes). A statement chain necklace that makes knots a chic embellishment.
5. Kain Label pocket tee ($88; Saks Fifth Avenue). A super-soft tee with preppy stripes can be dressed up or down.
6. Slouchy tote ($350; Tory Burch). A straw tote with a timeless shape suits the beach and work.

By Leslie Garry

Images courtesy of J.Crew, Nordstrom, Barneys, Tory Burch, Saks Fifth Avenue, and Lori’s Shoes

I was raised a suburban girl, but I was born to live in the city. From the shopping to the nightlife, Chicago has as many places to see as Sarah Jessica Parker has Manolos. These places—boutiques, festivals, parties, fashion shows, and more—beg for my attention, and I’m more than willing to oblige. Whether I’m heading to work or a wine bar, I’m a city girl on the go, so it’s important that my wardrobe keeps up with wherever the day and night takes me. Incorporating a sense of urban sophistication, comfortable silhouettes, and au courant trends, my spring must-haves are built around a day planner brimming with meetings, parties and, of course, shopping. Here’s how I’m able to look great all day without an unnecessary wardrobe change.

Clockwise from upper left:

1. Racerback tank in “Imperia Beige” ($50; Banana Republic). A basic that’s essential for summer layering.

2. White fitted button-up shirt ($44; Gap). A true classic that’s polished enough for day and easily accessorized for night.

3. Aviators by Gucci ($275; Nordstrom). Aviators add a slight edge to an otherwise understated outfit.

4. “Christine” black pump by Calvin Klein ($98; zappos.com). The cutout designs adds interest to a timeless heel.

5. Ankle Cigarette Jean by BDG ($40; Urban Outfitters). This skinny jean goes with everything, and the price is just right.

6. “Kali Tank” by Zamrie ($78; Zamrie; 1213 W Diversey Avenue, by appointment only). The hand-painted print on this silk top is breathtaking.

7. Fold-over bag by Marc by Marc Jacobs ($466; farfetch.com). When going from work to play, this bag has the storage room to carry everything I need.

8. Scalloped zipper cardigan in black ($98; J.Crew). This ladylike cardigan adds the finishing touch to a sundress or tank.

9. “Spring Break Scarf” ($18; Francesca’s Collections). This scarf adds a touch of color and is perfect for those breezy Chicago days.

10. Leather “Bailey” jacket by Cynthia Steffe ($525; Perchance; 3512 N. Southport Avenue). This lightweight yet luxurious jacket is my alternative to the omnipresent blazer.

By Danielle Parker

Images courtesy of Banana Republic, Gap, Nordstrom, zappos.com, Urban Outfitters, Zamrie, farfetch.com, J.Crew, Francesca’s Collections, and Perchance

Whenever I go shopping, I gravitate toward classic pieces with a fresh twist. The timelessness of taupe, white, gray and tan, combined with interesting shapes and cuts, is just that. From menswear to bohemian, neutral pieces come from a variety of inspirations, but they always create looks that are impossibly chic and effortlessly cool. Here are some neutral garbs that’ll have you in the buff too.

1. House of Harlow “Sunburst” ring ($50; revolveclothing.com). This cocktail ring beacons attention without being too flashy or overpowering.
2. A look from 3.1 Phillip Lim’s Summer 2010 collection. Proof that head-to-toe neutrals are totally chic yet cool.
3. Gap straw fedora ($17; Gap). With so many fedoras out there, I love the simplicity of this two-toned style.
4. Paloma Barceló “Marina” espadrille ($195; net-a-porter.com). The straw and suede materials on this wedge give it rich texture.
5. Pitaya pleated shorts ($26; Pitaya; 1463 N Milwaukee Avenue). Shorts are the quintessential summer staple, and I love the breeziness of this style.
6. No. 6 silk romper ($318; Steven Alan). The lightness of this romper can be anchored with an edgy belt.
7. T by Alexander Wang tank dress ($105; Alexander Wang). The T line is my favorite for tees, but this dress—worn with a fedora, classic belt and gladiator sandals—is a summer go-to.
8. Stella McCartney silk slub “Hibari” jacket, lace “Ruma” top, and silk slub “Shiro” trouser ($1,895; $1,435; and $955, respectively. All by Stella McCartney). This look is the epitome of understated glamour.
9. See by Chloé single-breasted blazer ($515; farfetch.com). A white blazer can be worn over everything. My favorite combo for summer is with jean or silk shorts. You can really mix it up.
10. J.Crew belt in “glazed hazelnut” ($35; J.Crew). The color of this belt is an unexpected substitute for a brown shade.
11. Tylie “Madison” bag ($398; shebang; 1616 N Damen Avenue). A bag has to get me through the day, and I can fit anything is this one.
12. Maybelline Express Finish in “Sheer Satin” ($3.50; Target). With just a hint of pink, this polish is classic and totally on trend this season.

By Meghan Turner

Images courtesy of revolveclothing.com, 3.1 Phillip Lim, Gap, net-a-porter.com, Pitaya, Steven Alan, Alexander Wang, Stella McCartney, farfetch.com, J.Crew, shebang, and Target

Clockwise from upper left:

1. Classic trench in khaki from Banana Republic ($198)

2. Gray linen-blend trench coat from Old Navy ($50)

3. Mike & Chris “Marlton” trench with detachable hood ($341; Fix; 1101 W Fulton Street)

4. White trench with full skirt by Contrarian ($538; SHE Boutique)

5. Purple “Duchesse Silk Knotted Epaulette” trench coat by Burberry ($2,795)

6. “Ink Trench Coat” by ASOS ($111)

7. J.Crew‘s “Icon Trench” in light khaki ($298)

By Meghan Turner

Images courtesy of Banana Republic, Old Navy, Fix Boutique, SHE Boutique, Burberry, ASOS, and J.Crew

By Danielle Parker

Images courtesy of J.Crew