Out Of The Woods?
It's also a perfect example of how Oliver does a good job of matching himself, but when it comes to others he struggles to relate---in both a literal and figurative sense. True, black and white is a classic combination, and perfectly suited to match Shane's black and red dress. But there's a sort of resistance, a tension, between the white and the red, a hesitation to fully integrate, if you will, one his journey in Higher Ground will erode and replace. It's a transition for which this suit serves as the foundation.
The Colors Of Hope
The Pastel Palette
During the early weeks of Shane's absence, Oliver adopts a more streamlined and harmonious overall look for the workplace. His shirt, tie and pocket square combinations are mostly light blues, greens and lavenders in some combination, where his tie and pocket square always match, and his colors remain relatively light and bright. Even as he adjusts to life without Shane, there's a hope for her return as Oliver attempts to fulfill the promise he made to find Gabe. It's a clarity of purpose that his harmonious work wardrobe reflects.
Oliver's wardrobe even makes a turn for the sentimental during the montage as we join him "handl[ing] things," like fixing the porch swing and tending the rose bush. He wears the same jacket from Lost Without You, and the blue and green plaid shirt from Truth Be Told. We even seen him wearing jeans---that's a first! Both of these looks he wore in Shane's presence, and each had a sentimental moment associated with either the outfit, or the item to which Oliver was tending, even eliciting a flashback to the final moments of From Paris With Love.
The longer he pursues it, however, the more dead ends he runs into, and his wardrobe begins to shift back towards blue, but this time a more muted version as his hope for finding Gabe wanes. It's brief, but you get the best sense of it during poker night. Not only is he visibly distant, but his tie is plaid comprised of blue hues. It's as if the passing time is starting to get to him. It hasn't saturated his shirt, which in this particular scene is light blue, but you get a sense it would overtake his shirt any minute. Fortunately, Ramon's idea about holding a Blues night at the Mailbox Grille infuses new life into the case, and into Oliver and his wardrobe, too.
That commitment is accompanied by a colorful second wind that shifts away from blue, back towards the pastel palette with which he began. As time passes, however, Oliver hits another wall not only in his search, but in his faith in Shane's return as well. Tired of waiting, Oliver hangs up from being on hold once more in his search for Hattie, and visibly decides to no longer be put on hold in waiting for Shane either, demonstrated by moving her desk to a far corner of the DLO, out of his line of sight.
At Poker night, Oliver not only verbally (outwardly) expresses his frustration for the first time, abandoning the game as a result, but you begin to see it permeate more elements of his wardrobe.
His suit is dark blue with an almost indistinguishable striped pattern to it, he wears a blue dress shirt and plaid blue tie. What's off is his pocket square---a deep maroon/red that reflects his clearly bleeding heart. A heart that admits to Norman "[he] doesn't know what to do."
When Oliver does decide what to do, however, we see a temporary return of the clarity and consistency of wardrobe that reflects his clarity of action. In D.C. his neutral tones are accompanied by a tie and pocket square that completely in sync and perhaps even a matching set. What's interesting is that they are both a light blue, a color previously associated with hope. Yet you also get a sense it's a subtle signal of the loneliness that led him there to begin with as he tries to assess the situation in the present.
Oliver's pining for Shane is so pervasive at this point it literally saturates every element of his clothing. Unable or unwilling to express the true depth of his pain and loneliness explicitly, it is visually beyond denial or control. Remember that in Shane's wardrobe analysis we drew the comparison between indigo as not only a color, but a construction of loneliness, and the depth of Oliver's is tangible approaching the end of the film.
When Oliver discovers Shane in the DLO, Oliver's entire wardrobe palette is completely flipped from the beginning of the film. It has transitioned from a near-miss color match to Shane, to a head-to-toe mirror in just about every way. While we'll investigate this more in depth soon, it's good to note, as it's also accompanied by Oliver's first outward verbalization of the internal loneliness he has silently carried throughout Higher Ground.
It's a new level of transparency that reflects the emotional fine-tuning that Oliver underwent in Shane's absence, and begets more long-awaited emotional transparency between the pair, establishing a much deeper hope for their future than wardrobe could ever adequately convey.