Best buys for guys

Jeans E Street Denim Co. (1876 First St, 847-433-8338) in Highland Park for its variety.
Suit “Buy the nicest suit you can afford.” Keep the prices down with end-of-season sales at Saks.
Jacket “This [look] never changes for guys, so it could be an investment piece.” Hunt down a casual, military-style blazer at Jake (3740 N Southport Ave, 773-929-5253; 939 Rush St, 312-664-5553, shopjake.com).
Essential accessory “The watch is a way to have individuality without going overboard.” Score a not-too-spendy leather cuff at The Silver Room (1442 N Milwaukee Ave, 773-278-7130, thesilverroom.com).

Lindsay Segal

Credentials After a stint in New York in production and editorial at Women’s Wear Daily and Vogue, the Chicagoan kicked off a career in styling and personal shopping five months ago—including a recent gig styling Wilco for the Grammys.

Must-haves for gals

Dress pants “It’s worthwhile spending at least $200. Get Theory pants at Bloomingdale’s.”
Black dress Havilah (869 N Larrabee St, 312-202-0012) constantly gets new merch and has great sales and lots of basic dresses in the $100 price range.
Trench coat “Who can afford a Burberry? [H&M has] them seasonally, so you can always walk in and find a trench” (pictured, $60).
Essential accessory A piece of vintage costume jewelry from the Antique & Resale Shoppe (7214 N Harlem Ave, 773-631-1151).

Best buys for guys

Suit Guise (2128 N Halsted Ave, 773-929-6130, guisestyle.com) for brands like Filippa K and Helmut Lang (pictured, $342). “I’m all about slim-cut suits.”
Jacket G-Star (1525 N Milwaukee Ave, 773-342-2623, g-star.com), for an all-purpose option (pictured, $200).
Jeans Denim Lounge (2004 W Roscoe St, 773-935-2820, madisonandfriends.com). “If you’re gonna wear them to the ground without washing them, it’s worth spending $150.”
Essential accessory “A funky belt shows that you’re a little fashion-forward but not over the top.” Check out options at Haberdash (1350 N Wells St, 312-440-1300).

Lisa Kingsley

Credentials It’s no surprise that the Evanston native advises forking it over for the frills—“they’re little reflections of your personality”—considering her line of work: WWD -approved, high-end handbags. When she’s not gearing up for the launch of her ready-to-wear line next fall, she’s manicuring personal clients’ wardrobes.

Must-haves for gals

Dress pants J.Crew trousers like a flowy merino wool in cream “because, honest to God, there is no chicer color you can wear than cream.”
Black dress Get the $30 safari-style, button-down shirt dress at Old Navy right now.
Trench coat The Simply Vera ($66 at Kohls) belted anorak trench for cheap.
Essential accessory A Nike leather high-top (pictured, $80) from Saint Alfred (1531 N Milwaukee Ave, 773-486-7159, stalfred.com). “You can wear it with a chic trouser.”

Best buys for guys

Jeans Levi’s (pictured, $58). “If you’re not Lou Reed, make sure your jeans are one size bigger than your waist size.”
Suit Hugo Boss.
Jacket Gucci. “It will last you ten years.”
Essential accessory The Lisa Kingsley white cobra skin wallet (kingsleyhandbags.com). “It’s so rock and roll.”