Urban Orchard Outing

Oct 05 2025

Brewery District Hop

Oct 05 2025

Brewery District Hop

Oct 05 2025

Creative Campaign

Oct 04 2025

Creative Campaign

Oct 04 2025

Creative Office Hours

Oct 04 2025

Creative Office Hours

Oct 04 2025

Metropolitan Mixer

Oct 04 2025

Metropolitan Mixer

Oct 04 2025

Executive Summit

Oct 04 2025

Vintage Bookstore Discovery

Oct 04 2025

Gabby's Work Presentation

Oct 04 2025

Office Hours

Oct 04 2025

Nightlife Rendezvous

Oct 04 2025

Gabby's Marketing Meeting

Oct 03 2025

Rooftop Revelry

Oct 03 2025

Gabby's Client Presentation

Oct 02 2025

Gabby's DJ Set

Oct 02 2025

Lincoln Park Cafe

Oct 02 2025

West Loop Dinner

Oct 02 2025

Gabby's Uptown Presentation

Oct 02 2025

business casual

Oct 01 2025

Creative Agency Meeting

Oct 01 2025

Gabby's Client Dinner

Oct 01 2025

Midnight Jazz Lounge

Oct 01 2025

Museum District Meander

Sep 28 2025

Rooftop Revelry

Sep 28 2025

Cityscape Sojourn

Sep 28 2025

Work Meeting

Sep 19 2025

Sep 17 2025

Hazy Morning Meeting

Sep 18 2025

River North Review

Sep 18 2025

Autumnal Bookstore

Sep 17 2025

Street Style Hunt

Sep 15 2025

Gallery Opening

Sep 15 2025

Gabby's Art House

Sep 14 2025

Gabby's Art House

Sep 14 2025

Gabby's Downtown Drinks

Sep 13 2025

Creative Office Showcase

Sep 12 2025

Evening Bistro Dinner

Sep 11 2025

Executive Edge

Sep 11 2025

Executive Edge

Sep 11 2025

Gabby's Curated Cocktails

Sep 11 2025

Gabby's Unveiling

Sep 10 2025

Gabby's Unveiling

Sep 10 2025

Gabby's Unveiling

Sep 10 2025

Gallery Opening

Sep 09 2025

Urban Jazz Night

Sep 06 2025

Marketing Mixer

Sep 06 2025

Elevated Sales Pitch

Sep 06 2025

Cool Weather Meeting

Sep 06 2025

Autumn Evening Soiree

Sep 06 2025

Urban Exploration

Sep 06 2025

Late Night Lounge

Sep 06 2025

Urban Advertising

Sep 06 2025

Urban Advertising

Sep 06 2025

Gabby's Art Walk

Sep 06 2025

Techno Odyssey

Sep 05 2025

Urban Arts Soiree

Sep 04 2025

Cool Weather Briefing

Sep 03 2025

Gabby's Pitch Presentation

Sep 03 2025

Tech Firm Happy Hour

Sep 03 2025

Afternoon Coffee

Sep 03 2025

Cool Weather Marketing

Sep 03 2025

Cityscape Client

Sep 03 2025

Gabby's Weekend Brunch

Sep 02 2025

New City Brews

Sep 01 2025

Gallery Opening

Sep 01 2025

easy looks for work with a cool edge or pop of color - Workwear Statement

Sep 01 2025

business casual- nicer shoes for this outfit

Sep 01 2025

Street Style Hunt

Sep 01 2025

Architectural Stroll

Aug 31 2025

Gabby's Client Connect

Aug 30 2025

Techno Pulse

Aug 30 2025

Artsy outfits for work - Creative Workspace

Aug 27 2025

Cool outfit for work with a pop of color - Artistic Office

Aug 27 2025

Cool outfit for work with a pop of color - Artistic Office

Aug 27 2025

City Exploring

Aug 26 2025

Cute and comfy outfit for work - Comfy Workday

Aug 26 2025

Cool transitional work outfit for cool weather - Elevated Transitional Office

Aug 25 2025

Cool transitional work outfit for cool weather - Urban Executive

Aug 25 2025

Ballpark Chic

Aug 25 2025

Gallery Opening

Aug 25 2025

a chic but casual look for work fun and chic looks for work with a pop of color - Boardroom Pop

Aug 20 2025

Urban Professional

Aug 15 2025

cool girl look for work - Downtown Gallery Opening

Aug 15 2025

cool girl look for work - Modern City Work

Aug 15 2025

cool girl look for work - Cool Girl Edgy

Aug 15 2025

Jul 29 2025

Jul 30 2025

Aug 07 2025

Downtown Bistro

Aug 14 2025

Gallery Gala

Aug 14 2025

Aug 14 2025

Aug 13 2025

Aug 12 2025