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Top 10 Questions a Stylist Gets From Women 40+

From the best jeans to how to slim your middle: simple answers you’ve been waiting for

By Becky MacCurtain

rack of gray sweaters
Photo by fancycrave for unsplash

I was the former accessories editor for More Magazine and now own my own style company, LBD Style Consulting, which helps accomplished women shop for and curate a wardrobe that shows off their personal style. These are the questions I get asked by all my clients on a regular basis.

1. How long should I hold onto something in my closet that I don’t wear?

I recommend letting go of an item that hasn’t been worn in over one calendar year (two clothing seasons). There are a few exceptions to this rule for items that have sentimental value or if you are undergoing a dramatic weight change such as pregnancy. It can be difficult at the moment to let something go, but you will always feel better after purging. The process is both therapeutic and necessary for maintaining an up-to-date wardrobe.

2. If I want to appear slimmer: what should I look for?

Most women make the mistake of hiding behind their clothes. They think that large, billowy clothing will make them appear smaller and hide what they don’t like about their bodies. The opposite is true. Oversize cardigans (my least favorite item) make women appear larger and frumpy.  Stick to tailored styles that show off your figure; you’ll be amazed what a few fitted styles will do for your confidence!

Also, try balancing the proportions by pairing looser silhouettes on top with slimmer styles below. For example, try a longer blouse — but with skinny pants. I coaxed one client into a more tailored style and people immediately started asking her if she had lost weight! She looked and felt like a different person without losing a single pound!

3. What do you recommend for disguising your midsection?

Most women find their midsections get less and less defined with age. Disguising doesn’t always work. But there are certain dress styles that are great at creating waists or the illusion of one. Look for styles with ruching, paneling, and detailing around the waist that can literally suck you in. A dress with a belt or tied-waist, such as a wrap dress, can help define the area as well. I personally like tied-waist dresses like this one from Alice + Olivia. I began wearing them after I was pregnant and they have remained a staple in my wardrobe. A peplumed item is also great for creating and defining a waist.

You can also distract the eye upward by wearing tops with interesting details or necklines. Fun costume jewelry (earrings, necklaces) can also show off your top half.

4. Do you have favorite pieces for business travel? What’s an easy item I can pack that’s appropriate?

Many of my clients are executives and are looking to add items to their wardrobes that can be worn at the office or on the road. I love a jersey blazer like this one from Bailey 44. It’s incredibly comfortable and looks chic over a tee, blouse, or a shift dress. Perfect for the plane, it feels like a sweatshirt but looks like a blazer. The best part is — it won’t wrinkle!

5. My office is getting increasingly more casual. How do I dress for business casual but still look polished?

I get a lot of questions about business casual these days. After years of adhering to strict dress codes, more women are loving the opportunity to dress in a more relaxed manner but are not sure exactly what that means. I also get this question from women who work from home and/or run their own businesses. While they may have more flexibility, they still need to dress appropriately when they go out to meet a client.

My first recommendation is always a dark clean denim jean (if denim is allowed). I also love a twill or sateen fabric in a classic jean like this from AG; it fits like a regular denim jean but is a bit more polished. A cropped jacket is also a great business casual piece to have on hand. Pair it with a nice tee shirt or shell with your black denim pant. It will pull together your look and make you feel more together. I particularly love these styles by Rebecca Taylor.

6. What is the most flattering style for a denim pant?

Most of my clients, especially those looking for control around their midsection, gravitate toward a high-waisted denim pant with a lot of stretch. I love the Le High Skinny by Frame and the MOTHER Looker style. I’m also a big fan of the cropped flare or kicked flare that’s out there right now like the Jodi Crop by AG.  I recommend this style to my pear-shaped clients who are looking to balance out their hips. It’s also a great style to show off any shoe in your closet. Pair them with an ankle bootie in the winter or a sandal in summer. I also love the AYR Shade asymmetric crop.

7. Where can I find the best tee shirt?

Sometimes the simplest pieces are the hardest to find. I am particularly fond of tees that are versatile — ones that can be worn at work under a jacket or out for brunch on weekends. While women have different preferences for the precise thickness or cut, I generally find that the J crew perfect Tee is in fact “perfect” for all occasions.

It’s tight enough to be tucked in for the office. It’s also thicker and less sheer than the popular “burnout” styles out there, making it more appropriate. I also love the Vince Essential Crew Tee and Everlane’s Cotton Crew.  

8. Are tights still cool? What color do I wear with what? Do I wear opaque tights or sheer hose? Can I wear tights for all occasions? 

Questions about tights come up all the time with my clients and the answer is very simple. One pair of well-made black opaque tights is all you need. I swear by Wolford Velvet De Luxe 66  tights, which come in the perfect level of opaque — and they last forever if properly cared for. If you own one pair of tights for the rest of your life it should be these. You can wear them with everything — in every color — including a cocktail dress. While at $49 per pair, they are definitely an investment.

9. Which items in my wardrobe should I spend big-investment dollars for and which are ok to buy on the cheap?

I work with women who have all levels of budgets and I love digging out the perfect pieces of clothing at every price point for them. There are some items I do recommend investing in, however. Since I believe that less is more in terms of wardrobe, investing in fewer, high-quality items that will last years is better than buying a lot of fast-fashion pieces that may fall apart, pill up, or stretch out after one season.

You should also invest in classic styles that are not trendy. I consider these six items the foundational investments for any wardrobe: a coat, blazer, a classic denim pant, boots, pumps, a shift dress. Classics never go out of style and are worth the splurge. Fill in around your investment items with cheaper, trendier pieces. Go for a blouse in a fun print or color or a piece of costume jewelry. Then if you tire of it, it’s easy to let it go without feeling guilty. 

10. What should I wear during transitional weather? 

A long-sleeve dress! I love dresses because they are so easy to throw on and you don’t have to worry about matching up separates. Dresses are especially great to wear in between seasons because they can be layered. If it’s cold, add tights, boots, and a blazer or a vest. If it’s warm, wear your dress with bare legs and sandals. If you are shy about your arms or feel cold at the office, find a terrific long-sleeve or ¾-sleeve dress. I love a printed or floral dress in chiffon or silk for this type of look, like this one from Equipment.

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