Dressing During Your Weight Loss Journey

Does it seem like everyone is shrinking? Whether they’re doing it the old-fashioned way through diet and exercise or embracing GLP-1 medications like Ozempic or Wegovy, the transformations are stunning. Shrinkers tell us they’re going through several sizes so quickly that clothing rental is a must. They’ve found buying new clothes at each stage is prohibitively expensive, especially for those using spendy weight loss drugs. Renting allows them to access a complete wardrobe for every notch on their belts without the commitment of purchasing pieces that will no longer fit in a few weeks. But where do you start when trying to dress an entirely new, unfamiliar body? I asked our stylists who have abundant experience helping Armoire members with this exact challenge. Here are their tips for dressing during your weight loss journey.
Embrace Transitional Wardrobe Pieces
Transitional wardrobe pieces are essential on a weight loss journey, offering versatility and comfort as your body shape evolves. Wrap dresses and tie dresses are particularly ideal, thanks to their adjustable fits that adapt seamlessly to changing sizes. Pants and skirts with elastic or adjustable waistbands provide a comfortable, long-lasting solution, while garments made with stretch fabrics, such as those containing spandex, deliver a forgiving fit that moves with the body. Stretch denim in skinny or straight-leg styles in a dark wash are ideal. They maintain a flattering shape while adapting to size changes.These adaptable options ensure you feel confident and stylish throughout every stage of your transformation.

Focus on Layers
Layering is another key strategy for dressing during a weight loss journey, as it adds polish and versatility without emphasizing fluctuating sizes. Cardigans and lightweight jackets are excellent options for creating a pulled-together look while offering flexibility to adjust to changing proportions. Single-button or open-front blazers add structure to any outfit and can be layered over everything from casual tops to dresses, making them highly versatile.Â
Long, slightly tailored tunics pair well with leggings or slim-fit pants for casual days. Stylists also recommend button-down shirts that can be worn open over a fitted tank. Layering them not only provides visual interest but also ensures comfort and adaptability, making it easier to navigate the transition with style and confidence. Look for those with adjustable roll-tab sleeves and stretchy fabrics for even more practicality.Â
Rent Key Staples

Starting with key staples is essential for building a versatile wardrobe that works through various phases of a weight loss journey. Renting classic pieces like black trousers and a well-fitted blazer offer timeless style and adaptability, while flattering as sizes change. Fitted camisoles, tanks, and leggings make great base layers. These can be paired with oversized sweaters, cardigans, or long coats to create a balanced, stylish look. Similarly, dark-wash jeans with a slight stretch provide a comfortable and flexible option that transitions seamlessly from casual to polished looks. These wardrobe essentials act as reliable anchors for a changing silhouette.
Highlight the Right Features
Highlighting favorite features is a powerful way to boost confidence and celebrate progress during a weight loss journey. Choosing styles that accentuate the wearer’s best-loved areas, such as V-necklines to enhance the décolletage. An A-line skirt will create balance and they’re forgiving at the hips and thighs while offering a structured look. They can highlight a smaller waist while skimming over problematic lower body areas. High-waisted styles accentuate the waist and provide a comfortable, flattering fit. Look for styles with a stretch component to adapt as sizes change. Fit-and-flare dresses emphasize the waist and flare out below, creating an hourglass shape that works beautifully on transitioning body types.

Accessories like belts are also a great tool to define the waist and create a more structured, flattering silhouette. By focusing on what makes you feel great, you’ll have a wardrobe overflowing with positivity and self-assurance.
Simplify with One-Piece Wonders
When finding a good fit among two or three pieces for an outfit feels challenging, opt for a one-piece wonder. Jumpsuits with elasticized waists, tie belts, or adjustable straps are both trendy and practical for fluctuating sizes. Dresses with an empire waist draw attention to the upper body while providing a flowy, forgiving fit over the midsection and hips. A maxi dress with an elastic or tie waist creates a beautiful silhouette and works well as the body transitions.
Emphasize Confidence
The experts agree: confidence truly is the best accessory. Dressing in flattering, well-fitted clothes can play a significant role in boosting self-esteem during a weight loss journey. Clothing that fits properly and highlights your best features will help you feel more comfortable and self-assured, no matter where you are in your transformation. Emphasizing confidence through thoughtful wardrobe choices encourages a positive mindset and allows you to focus on your progress and achievements, radiating empowerment and self-love with every step of your journey.

Dress for Your Body Shape
Whether you’re dropping pounds or adding them, dressing for your shape will help you look your best. Body shape is dependent on your bone structure and genetics, not your weight. You can be any body shape at any age, weight, or size. We created a popular body shape guide to help you find your body shape and to understand which styles and brands work for your body. Even better, we have curated collections for each shape.
Avoid Overly Baggy Clothing
But what about your old clothes? While it may be tempting to reach for oversized clothing during a weight loss journey, overly baggy pieces can often obscure the body and create an unpolished appearance. Instead, opting for tailored or semi-fitted styles strikes the perfect balance between comfort and confidence. These cuts highlight the body’s evolving shape without clinging too tightly, ensuring a flattering and refined look. Choosing well-fitted clothing allows you to celebrate your progress and present a more polished, put-together image throughout your transformation.
Rely on Clothing Rental
A changing body can alter how certain cuts and styles look or feel. Renting provides the freedom to experiment with new silhouettes, colors, and trends to discover what works best for your evolving shape. You can try different sizes and styles as your body changes, without fear of outgrowing or undergrowing items. This flexibility ensures you can always dress in something flattering and confidence-boosting. Plus, renting takes the emotional weight off of clothing. As sizes change, there’s no guilt about parting with pieces that no longer fit, making it easier to focus on the positive aspects of the journey.
A Clothing Rental Checklist for Your Weight Loss Journey
By incorporating these adaptable and flattering styles, you’ll feel confident and stylish at every stage of dressing during your weight loss journey.
Dresses
- Wrap dresses
- Tie dressesÂ
- Empire waist
- Maxi length
- Fit-and-flare
Tops
- Camisoles
- Tanks
- Tunics
- Button-downs
- V-necklines
Pants
- Elastic waistbands
- Slim fit
- Leggings
- High-waisted
Jeans
- Stretch denim
- Skinny
- Straight-leg
- Dark wash
Skirts
- Adjustable waistbands
- A-line Â
Outer layers
- Cardigans
- Single-button blazers
- Open-front blazers
- Lightweight jackets
- Kimonos
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