The Pieces That Will Give You the Perfect Wardrobe – Q&A with Stylist Catherine Sheppard

Laying a solid foundation for your wardrobe will help you mix and match your pieces easily and get more out of what you have.  The classic advice is to buy items like a good cashmere sweater, a pencil skirt, and a nice pair of trousers but I’ve longed for an updated list of basics that fit my life. Stylist Catherine Sheppard used her feminine and contemporary eye to share what every woman should have in their closet, what you can wear now and later in the fall, and short cuts for updating your wardrobe.

photos of Catherine and her office courtesy of Catherine Sheppard

I often see articles on the basic items every women should have in their closet (like this). What would be on your list of the top 15 items that make a killer wardrobe?

  1. – A great leather jacket
  2. Chunky watch in your favorite metal
  3. – A basic little black dress in whatever style reflects you best
  4. Plain pumps – black if you have dark hair, nude if you have light hair
  5. – Everyday carry-all handbag
  6. – A pair of Converse
  7. – A classic blazer in a modern, flattering cut
  8. Chambray shirt
  9. Something sequined (anything)
  10. Cutoff shorts
  11. – A fit-like-a-glove pair of skinny jeans
  12. Flat boots in your favorite style
  13. Statement necklace
  14. Metal bracelets that you can mix and match
  15. Metallic clutch

leather jacket – Walker, blazer – Topshop, sequin top – MICHAEL Michael Kors, chambray shirt – MiH Jeans, sneakers – converse, cut off shorts – Old Navy, jeans – Paige, dress – Vix ,necklace – J.Crew, watch – Pierre Petit, bracelets – Coach, pumps – J.Crew, flat ankle boots – LAutre, satchel – Mulberry, metallic clutch – J.Crew

Certain kinds of items can easily work their way into many outfits. In your opinion what should be your most versatile clothing piece?

Definitely your handbag. This is something that you may only switch out every so often so it’s important that you can grab it and walk out the door looking great in whatever outfit you might have on. I would suggest one in a fabric that’s appropriate for multiple seasons, and for day and night. Leather is probably your best bet, and go with a color that is in your general hair tone.

(from left) suede – J.Crew, satchel – MICHAEL Michael Kors, cross-body – Coach, black top handle satchel – Badgley Mischka, black tote – Mulberry, tote with cross-body strap – Dooney & Bourke

How would I wear this item to work, on the weekend, or for a night out? 

A good handbag won’t require any extra styling. You can just grab it and go! In order to make it work for both work and the weekend, get one that is not too slouchy or too structured, but right in the middle. I would recommend keeping a smaller clutch inside your handbag in case you make last-minute plans to go out at night.

satchel – Mulberry, black Minaudiere – Pour la Victoire

What three clothing items or accessories make the biggest difference when updating a wardrobe?

Jewelry, shoes, and a good top layer piece (like a jacket or blazer) are all so key when updating your wardrobe. Even if the rest of the pieces in your closet stay the same, you can make it look completely different by bringing in a few new jewelry pieces, a new pair of shoes, or a great blazer. These are all things that can be updated on a tight budget as well.

necklace – House of Harlow 1960, floral blazer – Topshop, strappy sandal – Alexander Wang

I like clothes that I can wear all year round. Are there any clothing pieces in particular that work well in both warm and chilly weather? 

A great pair of ankle boots can be worn with shorts or a summery dress, or with skinny jeans and a sweater in the winter. Lightweight scarves are great as an added layer in colder weather, and as a simple wrap in warmer climates.

ankle boot with cutout – Whistles, black ankle boot with buckle – Madison Harding, ankle boots – Rebecca Minkoff

Although I like to imagine that I can buy an unlimited supply of fabulous bags, realistically, I only have the budget for one great carryall. What qualities should I consider when looking for a bag that can take me from work to weekend?

If there is any part of your wardrobe not to cut corners on, it’s your everyday bag. I would try to find something that’s the best quality for your budget. A well-made bag is unmistakable and definitely worth a few extra pennies. This doesn’t mean it has to be a four-digit investment, but do your research and find something that is timeless, not too trendy, and perfect for your individual needs. A carryall is something you use extensively every single day – setting it down on concrete, digging through it to find your lipstick, throwing it on your car seat… it will really take a beating, so you want something durable. I would definitely go with a nice leather. Coated canvas (like the classic Louis Vuitton bags) is another great option.

croc-embossed tote – Longchamp, monogram tote – Louis Vuitton, striped reversible tote – Coach

While browsing through street style photos I often see someone with one special piece they wear over and over but that gives them a signature style (like the Delfina Delettrez hand bracelet often seen on Shala Monroque). When I go shopping, how can I look for versatile pieces that have character that won’t wind up in the bin of “clothes to donate” in six months?

Pieces like that usually tend to happen serendipitously. You never know when you will find that perfect thing that’s going to end up defining your style, and often times it doesn’t become a signature piece until you’ve had time to wear it for awhile and get attached to it. The best suggestion I can make is to look outside of the box. You probably won’t find your special piece at a store everyone shops at. It might be a fun vintage find, a unique gift from a stylish friend, or something you discover while traveling. Keep your eye out in unexpected places and listen to your gut!

What do you wish more women would try in their wardrobes?

I think a mistake a lot of women make is to limit pieces in their wardrobe to the first outfit they thought to wear it in. Mixing and matching is the best way to keep your wardrobe fresh and interesting. You can tuck that silk top into a pencil skirt, even though you usually wear it with skinny jeans, etc.

blouse – Tucker, skirt – Topshop, black tote – Proenza Schouler, ankle strap booties – Apepazza, jeans – Paige, clogs – Swedish Hasbeens, drawstring bag – Wendy Nichol, shorts – Old Navy

I’ve heard of stylists holding onto a gown or accessory that is “the one” until the right client and event comes along. Are there any clothing items you’re just dying to try on an upcoming styling project?

I often see a great dress at a vintage store that calls for a whole photo shoot to give it a moment in the sun, and I usually have to just file it in my brain until the right thing comes along. Right now I’m dying to style some edgier photo shoots or clients since I’ve been working with a lot more soft, romantic themes lately. I love it all though!

How far in advance should potential customers contact you for styling advice for an appearance or special occasion? 

It can happen in any time frame, down to the day of the event (yikes!) but coming up with the perfect look usually takes a lot of planning. It’s best to start about a month out, so there’s plenty of time to gather multiple different options until the perfect one comes along. Last minute changes are common, so it’s never a bad idea to have a Plan B look. For some events, like a networking party or industry event, it may not always occur to you to plan your outfit far in advance, but when the day arrives, you will find yourself wishing you had given it more thought. So anytime you are invited to something special, it’s in your best interest to call your stylist or start thinking about what you will wear sooner rather than later. You will be glad when the day comes and your perfect outfit is already figured out!

To find out more about Catherine or if you need help with a closet detox, styling for a big event, or personal shopping advice visit (She even offers virtual styling so you can get her great advice wherever you are!) 

photo courtesy of Catherine Sheppard

1 comment
  1. Jean Withers said:

    Can’t believe how Stylebook has changed my buying habits (before I buy I check my virtual closet to make sure I need possible purchase); and how many compliments I get about being “well-dressed”…”pulled together”, etc. I’m also about to take my 2 trip & have been to 2 big conferences this year. Never ever has packing been so easy!!

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