The Haute Seeker

Chic Summer Outfit Ideas to Wear All Season

If you are like me, you’ve had fabulous clothes from 2019 (and ones you bought for comfort in 2020) that you’ve yet to wear. This is the summer to wear those sandals that you never got to strut the city in, that purse that you’ve only worn to the grocery store (which the cashier loved by the way), and that top that only your roommate has seen you in (you had to give someone a fashion show after all).

This list gives you inspiration not only on how to wear your favorite summer pieces but where to wear them. From bottomless brunches on Sunday Funday to date night on Fridays, here are a few ideas on summer outfits and where to wear them this summer.

What to wear this summer in Chicago

Sexy analogues Combo for rooftop hops

This colorful combination will have all eyes on you instead of the views. The bright combination of red and orange is very flattering and eye-catching, especially in this fitted silhouette. Wear this look to your favorite rooftop during a day party or even for a night out on the town with your crew. If red and orange are not your colors, find two shades that are closer on the color wheel that are! Believe me, there is something for everybody.

Cool Shorts and a dressy top for SUMMERTIME festivalS

Whether it’s a bright t-shirt or an ornamented tank, this is a simple outfit option that will get you through any festival this summer. When you want to be cute yet casual, there is no better option than a pair of shorts. For this outfit, I paired a classic pair of khaki shorts, a semi-billowy tank top, fun sneakers, and a circular straw bag for a bit of boho edge.


This two-piece has been my go-to outfit for the past two summers. Because of the color and print, it is pretty timeless. This is a great look when you are bracing for a bottomless weekend brunch that will be filled with food and plenty of drinks. The high-waisted skirt can hide any “food babies”(no judgment) and low heels keep you balanced and comfortable as you continue to rage through the daytime hours.

When You should wear in these Chic summer looks

Options are endless when it is summer in your favorite city, but here are a few of my favorites:

  1. Summer Festivals: Outdoor Summer Concert Series, Printer’s Row Art Fest, Renegade Craft Fair
  2. Rooftops: The Godfrey, London House, Cerise
  3. Bottomless Brunch: Bar Roma, Whiskey Business, Hutch American Bistro

How to Shop These Summer Looks

Let us know in the comments where you are wearing your favorite summer looks outfits.

Subscribe today and discover the latest in fashion + style

Success! You're on the list.