BEST IN FEST From May 31 to June 2, Wicker Park becomes a 10-block shopping strip for the Do-Division Street Fest & Sidewalk Sale (do-divisionstreetfest.com). Your $5 donation will support three local elementary schools. On June 8 and 9, an estimated 30,000 art lovers will descend on the 64th annual Old Town Art Fair (oldtowntriangle.com) to shop for paintings, ceramics, jewelry, and other crafty finds. A $7 donation is requested.

NEW IN TOWN Cosmetics and skin-care boutique Cos Bar plans a June 1 opening in downtown Highland Park (442 Central Ave.), with a roster of high-end brands including Laura Mercier, La Mer, and Natura Bissé. On June 14, L.A.-based Splendid opens its first Illinois store at Westfield Old Orchard in Skokie. Along with supersoft tees and dresses, the new shop will carry women’s footwear and swimwear and kids’ clothes.

ETHICAL ATTIRE Shop sustainable styles from local labels such as Lara Miller and Silkutopia in the eco-fashion pavilion at the Whole Life Expo (1551 Thoreau Dr. N., Schaumburg), a celebration of all things holistic, held May 31 to June 2. Tickets ($20 daily, $50 for a weekend pass) can be purchased at wholelifeexpo.com.

FASHION SHOW On June 12, the rooftop at Castaways, North Avenue Beach’s ship-shaped bar, transforms into a runway for Come Sail Away, a showcase of sundresses and swimwear from half a dozen designers, including avant-garde styles by Ramsey J. Prince. The fashion show includes cocktails, live music, and fireworks. Purchase tickets at comesailaway.eventbrite.com.

Jay Gatsby believed in the green light. He also believed in dressing impeccably, as can be seen by Leonardo DeCaprio’s dashing portrayal of this literary character in the film version of The Great Gatsby, now in theaters.

As for me, I believe in the showstopping Gatsby line just launched by Brooks Brothers. Designed by double-Academy Award winning designer, Catherine Martin, who produced all of the men’s costumes in the Baz Luhrmann film adaptation, the collection does more than capture the nostalgia of roaring ’20s style—it inspires one to rethink all that’s beautiful about men’s fashion.  

Picking one item to recommend was as difficult as corralling Daisy Buchanan. The spectacular linen suits, the sumptuous shirts and equally sumptuous ties; the dazzling red, white, and navy regatta blazer. Browsing the pieces, it’s tempting to do anything to have it all—including becoming a bootlegger. 

I’ll just highlight one beauty: These white and brown spectator loafers. Crafted in England with tone-on-tone stitching and creamy calfskin, with leather insole and lining, they will turn a pair of taupe linen trousers into a spring/summer head-turner. 

Don’t take my word for it. Visit the store, breathe in the luxuriance, toss aside any inhibitions of looking like a dandy, and get something.

Gatsby, in the end, was a deeply tragic figure. You, by contrast, will be a fashion hero. 

$598 at Brooks Brothers, 713 N. Michigan Avenue

Chicago-based bracelet e-tailer BusyWrist has a motto—”the busier the better." I can get behind that motto. And, thanks to this company, I can wear it on my sleeve.

The idea is to go gangbusters mixing, matching, and stacking bracelets. The site is packed with wrist candy made of semi-precious stones, leather, and all sorts of prettiness, but it’s the pre-selected “stacks” that won me over.

There are those of us who wonder: “Does this clash in the effortlessly stylish way, or the trainwreck way?” Don't worry. The three-packs (which look awesome together but are far from matchy-matchy) are the way to go.   

Because who has time to stew over bracelet coordination?

$50 at busywrist.com

Photo: randolph street market

Opening Day

Randolph Street Market (1340 W. Washington St., 312-666-1200, randolphstreetmarket.com), the indoor/outdoor antiques bazaar sprawled across eight acres in the West Loop, kicks off its summer season this weekend (running from 10 a.m. to 5 p.m. on Saturday and Sunday). The opener takes everything there is to love about summer and rolls into one space: outdoor shopping, a beer garden, vintage carnival games and concessions, cooling stations and cabanas, fashion shows, and artisan food vendors.

Expect rows of booths packed with Parisian antiques from The Savoy Flea (thesavoyflea.com), vintage accessories from Richard’s Fabulous Finds (richardsfabulousfinds.com), wearables from indie designers like Shop NOV (shopnov.com), vintage Schwinn bikes from Mike's Classic Bikes (mikesclassicbikes.com), and stellar people watching.

Tickets are available online for $8 and at the door for $10. The first ten people in line Saturday score free admission and a chair massage to prep their bodies for a day of vintage picking.

Top Sales This Week

It’s a bit off the beaten path, but well worth the trek: West Town’s Annie O (324 N. Leavitt St., Suite 200, 312-421-8676, annieo.net) holds its spring sample sale on Wednesday from noon to 7 p.m. The sale is cash-only and features items from brands such as Tulle, Kensie, and Lucca Couture priced at least 20 percent off wholesale. Plus, there’s always a $10-or-less section.

The Clever Alice (17 E. Pearson St., cleveralice.com) pop-up returns to the Gold Coast for a summer sample sale from May 22 through June 2. Shop three floors of discounted garb from designers like Faubourg du Temple, 81 Poppies, and Tote—for up to 75 percent off retail. Doors are open Monday through Saturday from 10 a.m. to 7 p.m. and Sunday from noon to 5 p.m. (closed Memorial Day).

The Best of the Rest

• Sheryl Lowe—a jewelry designer, Hollywood makeup artist, and the wife of actor Rob Lowe—appears in the designer jewelry department at Neiman Marcus (737 N. Michigan Ave., 312-642-5900, neimanmarcus.com) from 10 to 4 p.m. on Friday.

• The suburbs are abuzz with art festivals this weekend. Shop various paintings, pottery, jewelry, and more at the Barrington Art Festival (Cook St. and Station St., amdurproductions.com), held from 10 a.m. to 5 p.m. Saturday and Sunday; the St. Charles Fine Art Show (Riverside Ave. between Route 64 and Illinois Ave., downtownstcharles.org), running Saturday from 10 a.m. to 6 p.m. and Sunday from 10 a.m. to 5 p.m.; and Schaumburg’s Prairie Arts Festival (201 Schaumburg Ct., prairiecenter.org), held Saturday and Sunday from 10 a.m. to 5 p.m.

• Nordstrom (nordstrom.com) begins its Half-Yearly Sale for women and kids on Wednesday. Shop the bargains online and in stores until June 2.

Relocations

After nine months on Ashland Avenue, West Town boutique Study Hall (2016 W. Chicago Ave., 312-733-4255, shopstudyhall.com) has moved to a larger space near the Chicago Avenue and Damen Avenue intersection. Check out the new digs at a grand opening party (complete with snacks and store discounts) on Saturday from 5 to 9 p.m.

While summer is the season of whites, white bags can be tricky—not only can they look a tad granny, but they get dirty in a twinkling.

No such problems with this Ferragamo stunner, which arrived at the Michigan Avenue store just a couple of weeks ago. (It's technically from the Fall 2013 collection.) The python exterior is black around the edges—where wear and dirt is most likely to show—with an irregular white blaze down the center. What's more, its leather-lined interior is roomy enough to hold your iPad (and other essentials).

A beautifully crafted Italian bag that you can carry from now through fall—without worrying about stains? Sign me up.

$1,950 at Salvatore Ferragamo, 444 N. Michigan Ave., 312-397-0464, or at ferragamo.com. (Note: This is Ferragamo's temporary location while it refurbishes its permanent digs at 645 N. Michigan. The move to the larger space is scheduled to happen in a few weeks.)

With all the hoopla around The Great Gatsby lately, Art Deco jewelry is having its moment. The loose, glittering glamour of the ’20s is hard to resist, and this piece from Lanvin is one of the best of the bunch.  

The pompom has a satisfying shimmy that makes you want to break into the Charleston, and the design is minimal enough that it can be paired with pieces inspired by any era. 

$950 at Lanvin, 116 E Oak St., 312-765-7075

I love the idea of a cheek stain, but it can be tricky to apply (“stain” being the operative word, here). And I like the velvety consistency of a cream blush, but it often lacks staying power.

Which is why when Josie Maran released a new Coconut Watercolor Cheek Gelée, my eyes lit up.

The gelée combines the long-lasting pigment of a stain (up to 14 hours) with the softness of a cream for a luminous finish. Because it’s infused with coconut water and argan oil, it’s also incredibly hydrating. A splash of coconut water is just what these cheeks ordered.

$22 at sephora.com

Thirty-year-old Eli Naeher founded Inland Clothing in Chicago last year with the idea of selling high-quality, classically-styled men's basics at a fair price—and all crafted in the U.S. The one-man operation has an online presence only, and ships all orders out of its Chicago warehouse, but Inland has shown up at pop-up markets like NorthernGRADE and this past Sunday's Dose.

Naeher seeks out the best small-batch manufacturers across the country (New Jersey-based Individualized Shirts provides Inland's men's dress shirts, the only item they have made in-factory for 50 years) but keeps it local too (Chicago-made clothing from Domestic Workwear.)

"Well-made clothing shouldn't be a luxury," says Naeher. "It should be accessible to everyone."

Closet fixtures like bridle leather belts and twill work pants are easy on the eyes, but it's the no-frills pocket knife and rubber-duck-yellow duffel (pictured) that will stop you in your mouse clicks. The humble bag's durability will not let you down, and Inland's collection is sure to follow suit.

$70 at inlandclothing.com

Short shorts can be the base of sexy getup or the culprit of a fashion no-no. I think the key to pulling off the bare-legged look (other than the obvious—toned gams) is what you've got going on above the shorts. Translation: When showing a lotta leg, it’s probably wise to show less arm, chest, and midriff.

That’s why this oversized top—made right here in the city by Edith Hart—will soon find its way into my closet. With a bit of understated detail (scooped neckline, dolman sleeves), it's the ideal mate to my new lacy mini-shorts. Now, to work on these pasty-white legs...   

$60 at Edith Hart, 1917 N. Damen Ave., 773-252-3350