What to wear? It’s the eternal question for many of us. Whether dressing for the day, a special occasion, or just trying to feel confident in our clothing, having a curated wardrobe makes all the difference.

My quick answer? Build your closet around classic, versatile pieces—items that mix and match effortlessly and never go out of style. Some might call it preppy, a term we used back in the day for solid, comfortable, tailored clothing in a cohesive color palette.

Wardrobe Staples: The Must-Haves

Tops & Layers

• White Blouses & T-Shirts – Always have plenty. They’re the foundation of countless looks.
• A Beige or Cream Oversized Crop Wool Sweater – Handmade or thrifted, this staple is both functional and stylish. It can have a funky shape but should remain versatile.
• Blazers (At Least Two) – Sourced from your favorite thrift store, a blazer is perfect for meetings, conferences, or those unexpected moments when you need to look put together.
• An Oversized Jacket or Coat – A black trench (lining removed) works wonders for layering while staying sleek. It pairs well with leggings or slim jeans for a balanced silhouette.

Bottoms & Dresses

• Slim Jeans or Leggings – Despite trends, a well-fitting slim silhouette is practical, flattering, and ideal for layering under oversized pieces.
• Wide-Leg Pants – If this style calls to you, wear them with a fitted top for a balanced look.
• A Pair of Black Pants – Whether tailored or denim, black pants are an all-occasion essential. They’ll have you ready for impromptu events like ushering at a play or helping at a formal gathering.
• Your Everyday Jeans – The perfect pair for your body type. A light wash can look effortlessly sexy and casual. Paired with a blazer, t-shirt, and practical shoes, you embody smart-casual style.
• A Denim Skirt– long or short makes for ease of style stepped up.

T-Shirts: The Five Essentials

1. Mock Neck (Sleeveless or Long Sleeve) – Always polished under a jacket or sweater.
2. Crew Neck Long Sleeve – Great under a tied-up blouse for an added layer.
3. The Perfect Short Sleeve Tee – Fit is everything.
4. Cropped Short Sleeve White Tee – A personal favorite.
5. Graphic/Advertisement Tee – Ideal for workouts or a laid-back “don’t-care” vibe.

Dressing to Impress

When you truly want to look great and feel confident, know your body type and what works best for you.

For me, a twill jumpsuit is my go-to. It’s flattering, but sometimes, I want an outfit that makes it clear I put in extra effort.

A dress with pockets and tailored details often does the trick. Whether you prefer a structured dress, a flowy maxi, or a bustier style, the key is flattering fits and quality fabrics.

• Vera Wang’s department store dresses are an example of affordable yet elegant designs with rich colors and great tailoring.
• Target dresses are cute designs but don’t have the same refinement or fabric quality.
• Higher-end designers tend to provide better fit and fabric, making an investment piece worthwhile.

Accessories & Statement Pieces

• A Bustier Vest – Tight like a corset, perfect for layering over oversized shirts, t-shirt dresses, or even worn alone.
• The “Fancy Dress” Collection – How many dresses do you really need? Ideally, one for:
  • A wedding
  • A funeral
  • A baby shower
  • A summer concert
  • A flattering date night

With these essentials in your wardrobe, making a final decision on what to wear becomes effortless. It’s about having key pieces that make you feel confident, comfortable, and prepared for anything life throws your way.

Pair with well fitting tennis shoes, all weather boots, classic loafers, or expensive sandals for comfort and style.

 If you are looking for how to make these pieces from your own closet read this blog, The Guide to Update Your Closet.

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Wardrobe Choices: Deciding What to Wear

What to wear? It’s the eternal question for many of us. Whether dressing for the day, preparing for a special occasion, or simply trying to feel confident in our clothing, having a well-curated wardrobe makes all the difference.

My approach is simple: build a closet around classic, versatile pieces—items that mix and match effortlessly and never go out of style. Some might call it preppy, a term we used back in the day to describe solid, comfortable, and tailored clothing in a cohesive color palette.

A well-rounded wardrobe starts with statement pieces that serve as a foundation. White blouses and t-shirts are non-negotiable essentials, always ready to pair with any outfit. A beige or cream oversized crop wool sweater, preferably handmade or thrifted, adds warmth and style with just enough personality to make it unique.

Blazers, at least two, should be a thrift store find—perfect for conferences, meetings, or those last-minute moments when looking polished is necessary. You never know when an unexpected opportunity might arise, like meeting someone at an event who wants to discuss a potential business collaboration.

A structured jacket or coat is another must-have. A black trench with the lining removed is an excellent choice, providing coverage against unpredictable weather while still maintaining a sleek look. Underneath, a pair of leggings or slim jeans ensures a comfortable yet stylish silhouette.

Slim jeans and leggings, despite changing trends, continue to be practical layering pieces, offering both warmth and a flattering shape. If the wide-leg pant trend calls to you, a fitted top creates the perfect balance. A solid black pair of pants is a necessity, whether tailored or denim. Black pants work for almost any occasion and are a reliable option for those unexpected moments when you need to dress appropriately—like serving food at a special event or ushering at a play.

Everyday jeans should be chosen carefully to suit your body type, and if you’re lucky enough to find the perfect pair, a light wash can look effortlessly sexy. A Denim Skirt– long or short (how to make your own here) makes for ease of style stepped up. Worn casually with a blazer, t-shirt, and practical shoes, they create a look that is smart without trying too hard.

T-shirts are another wardrobe essential, and having a variety of styles makes dressing easier. A mock neck, whether sleeveless or long-sleeved, is always polished under a jacket or sweater. A fitted long-sleeve crew neck works well underneath a tied-up blouse, while a well-fitted short sleeve t-shirt is essential for almost any occasion. A cropped short-sleeve white tee happens to be my personal favorite, offering a modern, stylish edge. And of course, a well-worn graphic or advertisement t-shirt is perfect for workouts or those casual, effortless days when looking polished isn’t the priority.

When it comes to dressing with intention, knowing your body type is key. Personally, I find that a twill jumpsuit flatters my shape, but sometimes I want an outfit that makes it clear I put in extra effort. A well-tailored dress with pockets always feels like the right choice. Whether it’s structured, flowy, or fitted like a bustier, the right dress enhances confidence. Vera Wang’s department store dresses are a great example of affordable yet refined designs, with flattering cuts and a rich color palette. Target carries cute dresses, but they often lack the pizazz and quality of higher-end options. Investing in better fabrics and tailoring can make all the difference in how a dress fits and feels.

Accessories and statement pieces can transform an outfit. One of my favorite layering pieces is a bustier vest that fits snugly, almost like a corset. It works well over oversized shirt dresses, giant t-shirts, and slim t-shirt dresses, but it can also be worn alone as a statement piece. Every wardrobe should also include a “fancy dress,” but how many do you really need? Ideally, just a few—one for a wedding, another for a funeral, one for a baby shower, a summer concert dress, and of course, something flattering for a special date night.

With these essentials in your wardrobe, making a final decision on what to wear becomes much easier. The key is having reliable, well-fitting pieces that make you feel confident, comfortable, and prepared for whatever the day brings. The right clothing choices go beyond fashion; they reflect who you are and how you want to present yourself to the world.