Breaking the Rules (Strategically)
When and how to bend your style guardrails
I champion a concept I’ve coined style guardrails: personalized style perimeters rooted in your unique coloring, body architecture, and aesthetic preferences. Style guardrails serve as a fashion North Star, helping you zero in on what truly suits you, shape a personal style that feels consistent and authentic, and sidestep costly mistakes.
Identifying style guardrails—and building wardrobes and outfits that reflect them—is something I help clients do every day. Before I recommend an item, I evaluate it against each client’s guardrails. But even with a clear framework in place, my clients and I are occasionally drawn to pieces that sit outside those lines. So—what then?
I’m a rule follower by nature, but sometimes, it’s okay to color outside the lines. The key is knowing when and how to do so intentionally, rather than by accident. I recommend using your guardrails to guide about 80% of your purchases and daily outfits—leaving just enough room for experimentation.
How do you know when to stay within your style guardrails, when to hug the edges, and when to cross them in service of personal style? Let’s dive in.
Hard boundaries
Some style rules are flexible—but others are foundational. These foundational guardrails are your non-negotiables: if you stray too far from them, your outfit stops working in your favor.
For example, I have soft, cool coloring, which means I’m best flattered by colors that share those qualities. Stray too far into warm or bright territory, and the effect is immediate. Mustard yellow makes my complexion look sallow and dull, so I avoid it in large doses—especially near my face. If a piece pushes against one of these hard boundaries—like wearing a color that drains me—it’s an automatic no. No amount of clever styling can override something that simply doesn’t suit you.
Defining your hard boundaries takes a mix of self-awareness and honest experimentation. Some people may need to avoid ultra-clingy fabrics that make them feel too exposed, or overly long proportions that swamp their frame. For others, it could be skipping minimalism because it feels flat, or eschewing fussy details that clash with their personality. You establish these boundaries by identifying what consistently undermines the way you want to show up.
Flexible guidelines
Some style rules are open to interpretation. These are the areas where your personal style can stretch—where you have room to experiment without losing your visual identity.
Because of my athletic build, square shoulders, and narrow, angular facial features, I tend to look best in fitted, structured silhouettes with crisp lines—think cropped jackets, cigarette pants, A-line skirts, and tailored mini dresses. Boxy tees and sharp blazers work well too, especially when they hit at just the right spot on my frame.
But I’m often drawn to pieces that fall just outside those lines—like oversized, chunky knit sweaters. This is where creativity comes into play. If a piece bends a rule, I can usually restore a sense of equilibrium with thoughtful styling. Pairing a voluminous sweater with slim, ankle-baring pants, structured flats, and a sharp crossbody bag helps balance the proportions and keeps the look feeling dynamic and self-assured—qualities that reflect my personal brand. These occasional pieces are easier to integrate when I’m still honoring other elements of my style guardrails, like wearing colors that flatter me most.
This mindset is especially useful when assessing the items in your closet that you like but rarely wear. Ask yourself: Does this piece break one of my guardrails—or several? Can I bring it back into alignment by anchoring the rest of the outfit in what works for me? Sometimes, a small adjustment—whether it’s a shift in proportions, a color pairing, or the right accessories—can make a piece feel aligned again. Bending your guardrails thoughtfully, rather than abandoning them altogether, allows for creativity without compromising consistency. It may even help you rediscover hidden potential in your existing wardrobe.
Intentional departures
Every now and then, it’s worth stepping fully outside your style guardrails—on purpose. You might choose to wear something that doesn’t reflect your style in the conventional sense, but feels expressive, adventurous, or perfectly suited to the moment. You’re not flexing a rule—you’re choosing to step beyond it.
Intentional departures work best when they’re grounded in self-awareness. You know which elements fall outside your usual framework, and you’re okay with that. Maybe it’s a silhouette that leans more feminine or edgy than your typical look, or a color that sits just outside your palette but captures the spirit of the setting. The key is that the piece aligns with a clear intention—whether it supports the mood, suits the occasion, or reflects a version of yourself you’re leaning into.
I occasionally make these choices myself. I recently wore a '60s-inspired, tea-length dress to a Mad Men party—a clear departure from my usual style. Decidedly retro, sheer, floaty, and feminine, the dress suited the spirit of the event. I didn’t try to make it feel like “me” in every way—I embraced the moment and enjoyed wearing something that expanded my range.
The goal of intentional departures isn’t to dilute your personal brand—it’s to stretch it. When you break your own rules with clarity and purpose, you give your style room to evolve without losing what makes it yours.
Guardrails are a framework, not a cage
When you understand your guardrails, you gain the freedom to follow them most of the time, flex them when needed, and break them—intentionally—when the moment calls for it. The goal isn’t rigid adherence; it’s self-expression with clarity and purpose.
Knowing your guardrails creates space for both confidence and creativity. If you’re unsure what yours are, I’d be happy to help you define them.