How to Dress Over 40: Insider Advice from a Personal Stylist

Reading: How to Dress After 40

How to Dress After 40

Stylist Leslie Hsu answers your most pressing fashion questions

By Leslie Hsu

As part of the May issue of TheCovey magazine, we interviewed Leslie Hsu, the style genius behind LesliesFinds — a personal styling service run almost entirely on social media — about how she turned her passion for fashion into a business. Upon publication of the article, Leslie promised to answer all of your pressing style questions. Here are the top 4 questions, with answers. 


1. I’ve lost quite a bit of weight recently — maybe 15 pounds, but it translates to two clothing sizes. I’m still in the process of losing more, and I don’t want to invest in new clothing until I get there —wherever there is! In the meantime, what are some good strategies for making due with what I’ve got, adapting, purging (totally giving up on vs. doing some tailoring), etc.

Great question and congrats on the weight loss! As for making due with what you’ve got, I would go through your closet and pick out the pieces that fit and flatter your new slimmer body — anything drapey that falls against your body like a maxi dress or a great fitting pair of culottes — those will never go out of style. Often items look even more flattering when they drape/fall rather than fit tightly, so many of your things might still look good on you, if not better. As we get older, I think that loose and drapey fits can look effortless and sophisticated.

As for denim, watch out for those majorly low hip-hugger jeans — unless they have the most incredible skinny leg fit, it might be time to update to a higher waist fit and/or some more wide-leg or boyfriend fits. Something else to consider is the length of your dresses/skirts/shorts — I personally find it harder as I get older to wear short shorts. Shorts with an inseam of 1.5”-2” used to work, but now I feel more comfortable with an inseam of 3” and a looser, more relaxed and effortless fit. These are my favorite example of age-appropriate hip jean shorts … not one pair returned!

I’m not so sure about adapting and tailoring without having seen your clothes firsthand, but those two things are sometimes trickier than they sound. Tailoring doesn’t always have an ideal result and then you’ve spent money and time for nothing. These days, I have found it’s often more cost effective to buy some new fresh pieces to wake up your wardrobe. As you can see from my posts, fashion and fun don’t always mean pricey. Fast fashion is here to stay so let’s make the best of it. It’s amazing what a few new well-fit key pieces can do to your look when mixed and matched correctly. I try to post staples that are worth way more than the actual price tag, easy and fun to mix and match.


2. My feet have fallen and they can’t get up! No more heels for this cowgirl. I LIVE in Birks all summer and Uggs all winter, and that’s okay in Montana. But when I need to glam it up…what to wear on my tired feet??? Also, when I’m in the city, usually I’m pounding the pavement from editor to editor and gig to gig, so I need to be comfortable too. Help?

I get that. I love my beautiful heels but my life doesn’t require that I wear them often, so the shoes I wear day-to-day tend to be comfy and cool. I live in and love all my platform sneakers! I have collected quite a few and have found a few pairs of super comfy “dressy Birks”! Classic, slim flip flops and black patent TKEES can also be effortlessly dressed up with a cute summer dress!


3. I can tell from a prior video that Leslie is tall, but if she has any styling tips for petite women, I’d love to hear them!

I’m 5’4″. I would say the trick is proportion. I often like my pants cropped because I think it makes my frame look taller (exposed ankles and heels can do wonders!). Another trick I like is wearing high-waisted pieces (the high-waisted denim skirt I just posted is super elongating), or a drapey dress that ties high up on your waist would work too. Platform sneakers are always cool!


4. Where else can I get clothes and accessories that have been put to the test AND have detailed descriptions AND the price is right?

Well, I think going with a personal stylist who you trust is your best option for tried and true, but perhaps if you don’t want to go that route, use the help of the sales specialists in your favorite stores (big department stores have stylists on the floor and some retail chains as well). Finding someone to help you who has put each piece to the test can save you time and effort. Good luck, and let me know if I can help!


Want more advice on how to dress age-appropriate (and still look great)? Join us for our next Coffee & Conversation on June, 6th at 8 pm EST. Personal stylists Leslie Hsu and Tania Sterl, founder of Founder of Sterl on Style, will be our guests! 


ICYMI: Watch Leslie revamp Lesley’s closet here. (Wondering what the heck ICYMI stands for? Read this essential post on acronyms you need to know.)



4 Secrets to Age-Appropriate Dressing

Why I Decided to Pose Nude at 55

How Well Are Your Feet Aging?


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