Designed & stocked in the UK
Pentlebay is based in Hertfordshire in the UK. All Pentlebay clothes are designed & stocked in the UK.

How To Wear It

How to Dress Between Summer and Autumn: Transitional Tips

Striped top

As the heat of summer begins to soften into crisp autumn breezes, your wardrobe may feel stuck between two seasons. One day it's blazing hot, the next you need a light jacket - and suddenly you're wondering how to dress for a season that doesn't quite exist. Welcome to the transitional phase!

The good news? This "in-between" season is full of layering opportunities, textures, and fresh styling options.

Transitional fashion helps you stretch your summer wardrobe while slowly integrating fall staples. It's also a sustainable approach - think layering, re-styling, and reusing what you already own with a few on-trend autumn pieces.

Whether you're headed to brunch, work, or a casual coffee date, these transitional outfit ideas will keep you looking polished and seasonally appropriate.

1. The Summer Dress + Knit Combo

Outfit Idea:

  • Tiered midi dress
  • Cropped neutral knit
  • Ankle boots
  • Crossbody bag

Style Tip:

  • Go for a long-sleeved dress or layer a soft knit over a summer dress that gives it an autumn-ready vibe.
Tiered shirt dress
Striped tee

2. Light Blazer + Denim Shorts

Outfit Idea:

  • White stripe fitted tee
  • High-rise denim shorts
  • Oversized blazer
  • Loafers or trainers
  • Gold jewellery

Style Tip:

  • This smart-casual outfit is perfect for warm afternoons that cool off by evening. Swap shorts for jeans when the temps drop further.

3. Midi Skirt + Long-sleeved Top

Outfit Idea:

  • Lightweight midi skirt
  • Lightweight long-sleeved top
  • Denim or leather jacket
  • Heeled ankle boots

Style Tip:

  • Midi skirts offer coverage without overheating. Pair them with fitted long-sleeves and a jacket.
Tiered skirt

4. Wide-Leg Trousers + Cardigan

Outfit Idea:

  • Neutral / black wide-leg trousers
  • Loose stripe tee
  • Trainers or sandals
  • Layer on a jacket or cardigan

Style Tip:

  • This is ideal for the office. Neutral layering keeps it chic without feeling heavy.

Some Must-Have Transitional Wardrobe Staples

  • Layer-friendly dresses and midi skirts
  • Lightweight knits
  • Denim jacket
  • Blazers
  • Long-sleeve basics
  • Ankle boots, trainers, loafers
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