Winter in Chicago has a way of forcing you to confront the realities of your wardrobe. The bone-chilling wind sliced through flimsy fabrics, and those oversized, dark sweaters that used to be my go-to were no longer adequate—not just because they didn’t keep me warm, but also because they no longer reflected my identity. As a transgender woman early in my transition, my journey to finding gender-affirming knitwear has been deeply personal, and I’m here to share some insights I’ve discovered along the way. For anyone navigating similar questions about style, warmth, and authenticity in cold weather, I hope my experiences offer comfort and inspiration.
Embracing Knitwear as a Form of Self-Expression
I built my wardrobe around hiding for years. Oversized, shapeless sweaters in blacks and greys served as shields, obscuring the body I didn’t feel comfortable showing. As I’ve begun to embrace my identity, I realized that fashion—especially something as cozy and versatile as knitwear—can be a tool for self-expression and empowerment. Knitwear offers endless possibilities: soft textures, flattering silhouettes, and vibrant colors that reflect the person you’re becoming rather than the person you used to hide.
The Importance of Fit: Finding What Works for You
When I first ventured into women’s knitwear, I was overwhelmed by the options. Fitted turtlenecks, chunky cable knits, cropped cardigans—each presented its own set of challenges and possibilities. What I’ve learned is that fit is everything, but it’s also deeply personal.
Here are some practical tips for finding a fit that feels good:
- Consider Body Shape: If you’re still adjusting to changes in your body, look for sweaters that highlight what you want to showcase and provide comfort where you need it. For me, this meant trying wrap sweaters, which create a lovely, feminine silhouette while feeling secure and cozy.
- Play with Length: Longer cardigans and tunics are excellent options if you’re self-conscious about your hips or thighs. Conversely, pairing cropped sweaters with high-waisted jeans or skirts can create a fun and flirty look.
- Experiment with Sizes: Women’s clothing sizes can vary wildly between brands, so don’t hesitate to try multiple sizes. Changing a size can significantly alter the feel and appearance of a piece.
Practical Layers for Brutal Winters
Chicago’s winter necessitates practicality, and maintaining warmth while showcasing your style requires careful consideration. Layering became my best friend as I explored knitwear options. Here are a few strategies that helped me:
- Base Layers: Start with a soft, fitted thermal or long-sleeve top under your sweater. This adds warmth without bulk and helps create a smooth silhouette.
- Chunky Knits: Chunky knit sweaters are lifesavers on freezing days. Look for pieces with interesting textures or patterns to add visual interest. Pair them with leggings or skinny jeans for a streamlined look.
- Cardigans for Versatility: Open-front cardigans allow you to adjust your layers throughout the day. They’re great for popping into a warm store after braving the cold streets.
- Accessorize for Extra Warmth: Don’t underestimate the power of scarves, gloves, and hats. Choosing bold, bright accessories can complement neutral sweaters and add personality to your look.
Layering Techniques for Different Body Types
Layering is more than a practical solution for staying warm—it’s also a fantastic way to create flattering outfits that align with your body type and personal style. By mixing textures, lengths, and fits, you can build a look that enhances the features you love while keeping you cozy in the cold.
For Hourglass Shapes
If you have an hourglass figure, emphasize your waist with layering pieces that cinch or skim the body. Here’s how:
- Base Layer: Start with a fitted thermal or camisole to hug your curves and create a smooth foundation.
- Mid-Layer: Add a slightly fitted sweater or a wrap-style cardigan that highlights your waist.
- Outer Layer: A belted coat or longline cardigan can further accentuate your shape, offering both warmth and structure.
For Pear Shapes
For those with wider hips and a smaller upper body, layering can balance proportions beautifully:
- Base Layer: Opt for a close-fitting thermal top in a neutral or light color.
- Mid-Layer: Choose a sweater with embellishments, patterns, or a wider neckline to draw attention upward.
- Outer Layer: A-line or trapeze-shaped cardigans and coats can drape elegantly over the hips, maintaining a flattering silhouette.
For Apple Shapes
Apple-shaped individuals often prefer layering techniques that create definition around the waist while avoiding bulk:
- Base Layer: Look for a smoothing thermal tank or a fitted turtleneck.
- Mid-Layer: A lightweight, flowy sweater with an empire waist or a peplum detail works well to define the midsection.
- Outer Layer: Structured jackets or cardigans with vertical patterns elongate the torso and add balance.
For Athletic or Rectangle Shapes
If your body shape is more straight-lined, layering can help create the illusion of curves:
- Base Layer: A fitted camisole or thermal in a soft, stretchy material is ideal.
- Mid-Layer: Experiment with textured or chunky knit sweaters to add dimension and volume. Cropped or belted styles can also help define the waist.
- Outer Layer: Choose a tailored jacket or coat that nips in at the waist to enhance curves and add structure.
For All Shapes
Regardless of body type, layering is an opportunity to experiment and express your identity:
- Combine materials like wool, cashmere, and fleece to achieve warmth without bulk.
- Play with lengths—pair a cropped sweater with a long shirt underneath or a long cardigan over fitted pants to add visual interest.
- Don’t forget scarves, hats, and gloves as finishing touches to your layered look.
Layering isn’t just a survival strategy for the cold; it’s a creative tool to shape your silhouette and express your unique style. Experiment with combinations to find what makes you feel both comfortable and confident.
Exploring Colors and Textures
One of the joys of embracing knitwear is the opportunity to play with colors and textures. After years of hiding in dark, oversized clothes, I’ve found that brighter shades and softer fabrics can be incredibly affirming.
- Colors: If you’re just starting to branch out, try jewel tones like emerald green, sapphire blue, or deep burgundy. They’re vibrant without feeling overwhelming. Pastels can also be lovely for a softer, more romantic vibe.
- Textures: Ribbed sweaters, cable knits, and waffle weaves add dimension to your outfit. Cashmere and wool blends are luxurious options that provide warmth without sacrificing comfort.
Shopping Tips for Gender-Affirming Knitwear
Shopping can be intimidating, but there are ways to make it fun and rewarding:
- Explore Inclusive Brands: Many brands now prioritize inclusivity in their designs. Look for companies that offer extended size ranges and styles that cater to a variety of body types and identities.
- Try Thrift Stores: Secondhand shops are goldmines for unique, affordable sweaters. Plus, shopping sustainably feels good and allows for experimentation without breaking the bank.
- Ask for Help: If you’re shopping in-store, don’t hesitate to ask staff for assistance. Most associates are happy to help you find pieces that fit your needs.
- Shop Online Thoughtfully: When buying online, check size charts and read reviews. Many websites also feature models with diverse body types, which can help you visualize how an item might look on you.
Reflecting on Style and Identity
As I stood on Chicago’s frozen streets with my friends, snapping photos in front of landmarks and darting into stores for warmth, I felt a shift. I didn’t focus on hiding my body or blending into the background for the first time. Instead, I felt present—embracing the cold, the city, and myself. The sweaters I chose that day weren’t just warm; they felt like me. They told a story of transition, self-discovery, and a willingness to be seen.
For transgender individuals, finding gender-affirming fashion is about more than clothes. It’s about reclaiming your relationship with your body and celebrating who you are. Knitwear, with its cozy, comforting nature, can be a beautiful way to start that journey. There’s no wrong way to express yourself, regardless of your preference for bold, bright colors or neutral classics.
Self-Care Through Fashion
Winter can be a challenging time, both physically and emotionally. The cold months often bring shorter days, less sunlight, and a tendency to retreat indoors, which can amplify feelings of isolation—especially for transgender individuals early in their transition. During this season, fashion can be more than a way to stay warm; it can become a form of self-care, providing a boost to mental health and body positivity.
When you choose clothing that affirms your gender identity, you’re sending a powerful message to yourself: I am worthy of comfort, joy, and self-expression. This is particularly meaningful in winter, when it’s simple to fall back into old habits of dressing to hide rather than celebrate your body. Selecting a sweater in a color that makes you smile or a fit that flatters your evolving silhouette can brighten your mood even on the greyest days.
Wearing gender-affirming outfits also helps you reconnect with your body. For many of us, winter means bundling up in layers that can feel bulky and impersonal, which might exacerbate feelings of dysphoria. But embracing soft textures, flattering shapes, and vibrant hues can remind you that your body is a source of strength and individuality, deserving of warmth and care.
Additionally, fashion provides a small but meaningful way to combat the isolation winter often brings. Whether you’re meeting friends for coffee, walking along snowy streets, or even hopping on a virtual call, wearing clothing that reflects who you are can enhance your confidence and encourage you to engage with the world. And when you feel good in what you’re wearing, that energy radiates outward, creating opportunities for connection and joy.
As you navigate sweater season, think of each outfit as an opportunity to nurture yourself. Fashion doesn’t have to be about meeting societal expectations—it’s about honoring your journey and celebrating who you are, even during the coldest months. By choosing clothes that feel true to you, you’re not just staying warm; you’re also practicing kindness toward yourself, one sweater at a time.
Overcoming Body Dysphoria in Fashion Choices
Body dysphoria can make dressing—especially during the colder months—a challenging and emotional experience. For me, knitwear became a way to navigate this complex relationship with my body. The softness and flexibility of sweaters offered comfort, but finding styles that helped ease dysphoria while expressing my identity took some trial and error. Here’s what I learned that might help you on your journey.
Focus on Fabrics That Feel Good
Tactile sensations can be grounding when dysphoria intensifies. Soft, cozy materials like cashmere, cotton blends, or chenille can provide physical comfort and a sense of security. Avoid fabrics that feel scratchy or restrictive, as they can amplify feelings of discomfort.
Highlight or Minimize Features
Sweaters can effectively highlight your confident areas while subtly downplaying others.
- If you love your shoulders or arms, try a structured turtleneck or puff-sleeve sweater to highlight those features.
- If you prefer less focus on your chest or waist, opt for relaxed fits or tunic-style sweaters that drape comfortably.
Patterns and Textures as Tools
Textures and patterns can redirect focus away from areas of dysphoria. For instance, cable-knit designs or color-blocking can create visual interest while maintaining a flattering silhouette.
The Power of Layers
Layering can help manage dysphoria by giving you control over what’s visible. A fitted tank top or binder underneath can provide a base, while an oversized cardigan or cowl-neck sweater offers warmth and a stylish cover.
Embrace Your Style Without Pressure
Most importantly, remember that there’s no right or wrong way to dress. Fashion is deeply personal, and knitwear offers a beautiful opportunity to experiment with self-expression. Start small—maybe a cardigan in a color you’ve always loved or a sweater with a playful pattern—and see how it feels. Over time, you’ll find pieces that feel less like armor and more like a celebration of who you are.
By approaching knitwear with a balance of practicality, creativity, and self-compassion, you can create outfits that feel affirming and warm—inside and out. You can take your time and let your style evolve.
The Bottom Line
As we step into this sweater season, I encourage you to experiment, embrace color, and explore what feels right for you. Whether you’re walking the windy streets of Chicago, navigating the snowy suburbs, or just looking for ways to stay warm at home, let your knitwear be a source of joy and empowerment. Most importantly, remember that fashion is for you. It’s a tool for self-expression, not a box to fit into.
If you’re still figuring out what feels good, give yourself grace. Transition is a journey, and so is finding your style. Start with small changes—maybe a brightly colored scarf or a textured cardigan—and build from there. Over time, you’ll discover what makes you feel both comfortable and radiant.
Stay warm, stay true to yourself, and happy sweater season!
