Thrown for a loop

The problem
You’re invited to an impromptu dinner party. Free food and a viable excuse to skip the gym? Sounds good. Now all you need is a small gift for your host.

Loop solution Sure, you can always run to (1) Macy’s (111 N State St, 312-781-1000) to pick up a bottle of wine on the lower level. But wine is kind of, you know, obvious. Instead, help set the mood by picking up a little dinner music (we recommend The Bird and The Bee’s self-titled debut or Introducing…Rubén González by Rubén González) from (2) Reckless Records (26 E Madison St, 312-795-0878) or (3) f.y.e. (26 E Randolph St, 312-606-0899). (4) Florodora (330 S Dearborn St, 312-212-8860), the new boutique in the Monadnock Building, also has cute retro-theme aprons ($32) or rubber gloves with snazzy cuffs ($15) that are perfect for your hostess.

The problem
You forgot about a happy-hour networking event on the one day you’re on the casual side of “business casual.”

Loop solution(5) H&M(22 N State St, 312-263-4436) is an obvious place to turn for a fast (and cheap) fix, but we always say that H&M unofficially stands for “Hit or Miss.” Guys looking to dress up their look can always count on the sophisticated styles from (6) Jos. A. Bank Clothiers(25 E Washington St, 312-782-4432) in the Bank of America Building. The ties here aren’t cheap ($30–$135), but they’ll last a long time. And for the cost-conscious, we recently spotted a two-button poplin suit on sale for $97 (originally $295). Speaking of surprising finds, (7) Filene’s Basement(1 N State St, 312-553-1055) usually carries discounted stock from Barneys, as well as selections from designers (including Gucci and Prada) on the relatively cheap side. And while (8) Forever 21 (32 S State St, 312-977-2121) is known for its super-trendy—and
teen-friendly—selections, you’ll also find Diane von Furstenberg and Phillip Lim–inspired dresses for about $25 each.

Top, monogrammed stationery ($11) at Arts & Artisans; bottom left, Beehive Shoe Works; bottom right, "Corporate" apron ($32) and gloves ($15) at Florodora

Bottom left, Caroline Voagen Nelson

The problem
The calendar on your desk is so full, you didn’t even realize today is your favorite coworker’s birthday.

Loop solution It’s too easy to get sidetracked and shop for yourself at (9) Borders (150 N State St, 312-606-0750). Instead, fine-tune your options with a visit to the (10) Prairie Avenue Bookshop (418 S Wabash St, 312-922-8311). At this architecture-heavy shop, you’ll find a lot of new, used and print books, as well as reproductions of Frank Lloyd Wright renderings ($15 each; $50 for a set of four) that’ll look great on your officemate’s cube wall. (11) Arts & Artisans (132 N LaSalle St, 312-263-2333) has a wide variety of last-minute gifts, including pop-up greeting cards ($6), monogrammed stationery ($11) and sterling-silver earrings ($25–$29). You can also splurge on a gift at the boutique in the (12) W Hotel–City Center (172 W Adams St, 312-332-1200). Gifts include Jonathan Adler vases ($40) and a travel kit featuring some of the best of Bliss spa products ($25).

The problem
Your shoe breaks during the day, and you need to get it repaired so you don’t fall on your face.

Loop solution(13) The Shoe Hospital (318 S Dearborn St, 312-922-7518)will fix your soles ($14) and broken heels ($8) in about two days. (14) Sam the Shoe Doctor (175 W Randolph St, 312-372-2655) wouldn’t discuss pricing, but the shop will heal heels fast. Drop your shoes off by 9am, and they’ll be ready that afternoon. The new location of (15) Beehive Shoe Works (35 N Wells St, 312-541-0777) will not only repair a worn-down pair of heels for around $12 but it’ll also shine them, making them look brand new and ready for a walk around the Loop.