What to Wear for End of Summer | EP 107



So, it’s the end of the summer. What exactly does that mean for fashion people when it is still 90 degrees literally everywhere? Can you wear white after Labor Day? Do flip-flops go with wool pants? Should you shop the Labor Day sales? Is it a good time to buy summer clothes?  

Help us, Holly! What in the world do we wear when our brain says fall, but the thermometer says HOT? 

Turns out, many people are fashionably confused right now. Just because you are dying for those Pumpkin Spice Lattes to drop at Starbucks does not mean fall weather is here. Regardless of what part of the country you live in, it’s still very much summer weather.   

This week, we are talking about the awkward “end of summer” and how to survive it. You know what we are talking about: Just because you decided to buy a new jacket at a pre-Labor Day Celebration sale last weekend does not mean you can actually wear it yet. We’ll get there.

How many of us have been tricked by the start of the school year into wearing a bulky new sweater, only to end up melting by 11:30 am? Not only are you miserably hot, but you look ridiculous. Sorry, Boo. It’s still 85 degrees. I’m just sayin. 

Lucky for you, we are here to work it out. We’re going to tell you what to wear so you look age- appropriate and on-trend without looking like a fall bumpkin in flip-flops. 

Fashion Disclaimer: All this style advice is relative depending on where you live in the universe. It’s very important for you to know that you have Holly’s permission to dress in summer-weight clothing as long as you need because let’s face it, it’s hot.    

However, you are going to start watching what you are wearing. You are not going to wear sandals anymore. Nor sun dresses, shorts with tank tops, and no flip flops. No more thin spaghetti strap summer tops, or floral miniskirts.    

We need you to take baby steps. No need to bust out the leathers or the knee-high boots, or especially, Uggs!  Ew, no.

Nothing is weirder than walking down the street and seeing a person in a scarf and leather jacket right now. We are in what the fashion industry calls pre-fall or transition fall. So, what does that mean? It is exactly what it sounds like: clothes that you wear right before the calendar says that it’s fall. Which in this case, is September 22nd. 

What’s the secret to Pre-Fall? You transition by mixing a few your summer clothes with some lighter-weight fall clothes. It’s really simple once you know how to do it. You will be comfortable and stylish with these easy tips: 

Number 1: Do Not Switch Out Your Closet Seasonally

Don’t bother with turning over or switching out your ‘summer clothes” for your “winter clothes.” FASHION CRIME!  

If you’ve listened to us at all before, you know you should be keeping your closet organized so you always know what is in your closet. If you have so much stuff that you are hiding sweaters under your bed, go back to EP 106 and listen to “How To Clean Out Your Closet.” It is a life-changing episode, trust us.   

Here’s the problem. Let’s say you do get your fall and winter clothes out of storage, and then you take your summer stuff out of your closet. You are going to be very upset when you find out some things no longer fit, or are looking ragged, and maybe out of style! Now you are annoyed because you have a bigger project than you intended and frankly, you forgot what you even had. 

Just don’t do it. It’s not a great headspace to be in. You want to be in control of your wardrobe at all seasons. You can’t do that if half your crap is in storage.  

Number 2: What to Wear? 

(As always, be sure to follow along on Holly’s Pinterest board this week.)  

  • Try wide-leg pants with a tank top. You can pop a lightweight blazer over your shoulders if you like.
  • Wear an oversized white button-down shirt with a tank underneath. Be sure to roll up the sleeves for a breezy look. Pair that with a maxi skirt and a platform sandal, a chunky necklace and you’re good to go. 
  • Try the Mom jean! Baggy jeans very on trend right now with a light, sleeveless summer sweater and a short, white boot. Now understand this: baggy jeans are fine on six foot tall, size two models. If you are short, and you’re little in the middle but you’ve got much back, baggy jeans don’t look great. You can try a jean that’s looser in the thigh instead of a full on baggy jean. (Believe it or not, Guess jeans are back, and we are not mad about it.) 
  • Instead of white sandals or shoes, Holly is loving a white boot. Try a white cowboy style boot with a summer sweater. Pair it with statement earrings and gold stacked bracelets. Boom! (PS: metallic cowboy boots are in right now and don’t think Holly’s not going to get a pair of silver boots.)  

You can also try a strapless top or one-shoulder top with skinny jeans or fall trousers, and add chunky sneakers. This is a great way to execute a pre-fall look.  

  • Get yourself a bodysuit. They come in a million styles and a million price points, and you throw it on with those mom jeans. 
  • Holly can’t believe this next thing is back in style, but women are wearing dresses over pants again. In this case, take a slip dress or one of those dresses that are cut on the bias or sundress and you wear it over pants. It could be jeans or it could be a wide leg trouser. It’s totally up to you. Holly would totally wear this again with one of her slinkier dresses for summer with a very minimal shoe or bright colored flat. 
  • Super bright neon colors are in. We know. It’s ugly. But it’s really not on the right person. Anyway, if you can get this into your outfit, somehow, some way whether it be your jewelry, a bag, a shoe, earrings, a funky-colored jacket or even a pant is super on-trend right now. (Remember, when you wear something like that, this one piece is the star, do not upstage yourself by wearing too many brightly colored things that compete with each other.)  
  • So here is the good news about bags right now. Yes, you can totally still use your summer handbags, especially straw bags.  There are so many different types of wicker bags that Holly is crazy about right now so be sure to go to her Pinterest board for the week.

Number 3: What about Fall trends, you say?  

Well, Holly doesn’t know yet, because she has to go to Fashion Week and that is not until next week. So be sure to come back and listen to that episode to find out! 

And finally, Holly’s biggest tip of the week is to get your wallet ready, because Labor Day is the best time to buy summer clothes and accessories on sale, y’all! Stores have got to get the summer merchandise out and the full-price fall merchandise in. This is the best time to buy anything for summer! 

Pre-fall is just that. Mixing your summer with your lighter fall items to create a look that says you’re ready to transition your wardrobe into the next season. Buy with intention knowing you can wear something from season to season or at least layer with it. Having pieces that can be worn for multiple seasons builds a cohesive wardrobe.

From your favorite personal stylist and the only Holly you need to know….Holly Katz

Fashion Crimes Podcast

“The best friend you never knew you needed in fashion!”

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2 thoughts on “What to Wear for End of Summer | EP 107”

  1. Did you ever address wearing white shoes or white pants after Labor Day? I’m from Memphis (live in mid Missouri now) and my mother always said no white shoes, pants, purses after Labor Day. I listened to your podcast to hear your thoughts but never heard much about it.

    1. Hi there-thank you so much for your comment! Yes you can absolutely wear white after labor day. I like to wear it into transition fall-then it’s called ‘winter white”. Since you live in the north it will get colder quicker so you might consider white cable knit sweaters, jackets or a white cowboy style boot. Those are my favorite things to wear into transition fall. Please let me know if you have any additional questions!

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