The Tip Jar #1: Refresh Your Style with 3 Stylish Methods

Discover How a Closet Overhaul, Mood Board, and Capsule Wardrobe Can Reinvent Your Look

It seems the world is always eager for advice—just take a look at the notes section of any popular fashion Substack, where you'll find a treasure trove of fashion tips and a flurry of questions and responses from fellow fashion enthusiasts. I’m excited to introduce a new monthly article: The Tip Jar. Each month, I'll tackle questions, offer musings, and provide a merchandiser’s perspective to address those burning fashion queries. After all, we’re all a bit hungry for advice from time to time.

Today's tip comes from a reader who's looking to boost her confidence in her outfits and feels a bit discouraged about not having mastered her style even in her early 40s. Where should someone start when rediscovering their style?

I always appreciate these types of emails—they let me indulge in my secret obsession with research. (Perhaps I was meant to be an investigative reporter in another life, given how much I enjoy solving style dilemmas and watching true crime). Let’s tackle this challenge head-on together. I’ve identified three different approaches you can explore.

Here’s a closer look at each one:

The Closet Overhaul

This first approach is simple and practical. Start by trying on everything in your closet and taking photos of each outfit. Then, sort the clothes into two piles—one for items that make you feel confident and another for those that give you the ultimate ick. After donating the no-go items (after all, one person’s trash is another’s….), analyze the styles in the pile of favorites and find similar pieces online or in stores.

The Mood Board

The second approach is all about visual inspiration and experimentation. Begin by documenting styles you’re drawn to on Pinterest, Instagram, or from celebrities whose style you admire, and create a mood board. I’ve done some of your heavy lifting and found a few influencers, separated by age, to help kickstart your mood board (scroll below). Next, visit your local department store. (In NYC, I recommend Bloomingdale’s as the go-to destination for both budget-friendly and splurge-worthy clothing and accessories). Try on various styles that match your mood board and grab everything that catches your eye to see what resonates.

20’s

@KiernanShipka - Ms. Sally Draper herself is undoubtedly the coolest 24-year-old on the block. Her style is a perfect blend of playful sophistication and modern-classic flair. She crafts looks that are both fresh and timeless, with an emphasis on shorter hemlines

30’s

@VenitaAspen - This 30-year-old Bravo-lebrity has my full attention when it comes to style. She never shies away from bold colors and statement pieces. If you’re in the office full-time, check her out—her looks are always well-tailored and she seamlessly mixes affordable price points with luxury brands

40’s

@louisnicolasdarbon - Louis-Nicolas Darbon is a 41-year-old French designer and architect renowned for his commitment to craftsmanship and beauty. His style embodies a blend of classic charm and contemporary cool, mixing casual comfort with a touch of refinement—perfect for a hybrid-friendly lifestyle

The Capsule Wardrobe

The third approach focuses on building a solid foundation with a capsule wardrobe. Start by identifying the 10 essential items every wardrobe needs, such as a perfect white button-down, classic black pants, and a versatile denim jacket. These timeless pieces will form the backbone of your closet. Once this foundation is established, you can gradually add trendy items to keep your style fresh and dynamic.

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As you explore these strategies to refresh your wardrobe, remember that personal style evolves with each new decision and discovery. Which method are you considering trying first?

Did you enjoy our first installment of The Tip Jar? If you have future inquiries or feedback, feel free to fire away in the comments section.