May is that magical month where you can wear sandals with your sweater or bring out your breezy dresses without freezing.
It’s all about layering smart, leaning into florals (yes, still groundbreaking), and pulling out those sunny staples you’ve been saving all spring.
Whether you’re brunching outdoors, heading to the farmers’ market, or planning a spring-to-summer getaway, here are May outfit ideas that are stylish, comfortable, and made for that in-between season glow-up.
Light Knit + Flowy Skirt

Pair a breezy knit sweater with a midi or maxi skirt in a floral or solid pastel print. Add sneakers or ankle boots for comfort and edge.
Linen Pants + Tank Top

Keep it easy and breezy with lightweight linen pants and a tucked-in tank. Add a cropped denim jacket for cooler mornings.
Oversized Blazer + Bike Shorts

A neutral oversized blazer over biker shorts and a cropped tee = fashion-forward and comfy. Bonus: perfect for transitional weather.
Floral Sundress + Sneakers

Say yes to spring florals with a cute sundress. Dress it down with white sneakers and a denim jacket for a casual day out.
Romper + Woven Accessories

An easy one-and-done romper with espadrilles, a straw bag, and gold jewelry is perfect for sunny May afternoons.
Lightweight Trench + Jeans

Still chilly? A neutral trench coat layered over a white tee and straight-leg jeans is classic May layering done right.
White Button-Down + Denim Shorts

For warmer May days, pair a crisp button-down with cutoffs and sandals. Tie it at the waist for a little shape.
Matching Knit Set

A knit two-piece set (like a skirt + top or shorts + cardigan) in beige, blush, or ivory is cozy enough for spring but breezy enough for May warmth.
Cropped Sweater + Maxi Skirt

A cropped long-sleeve sweater paired with a floaty maxi skirt gives you just the right amount of cozy and flow.
T-shirt Dress + Baseball Cap

This off-duty model combo is perfect for errands, iced coffee runs, and low-key weekends. Add chunky sneakers or flat sandals.
Silk Camisole + Trousers

Dress it up a bit with a silky cami tucked into high-waisted trousers. Add strappy sandals or mules for a polished May date night look.
Utility Jacket + Mini Dress

Layer a lightweight utility or shacket over a flirty mini dress for that perfect balance of soft and structured.
Neutral Jumpsuit + Statement Bag

A solid-color jumpsuit in beige or sage green looks effortless. Let your accessories (like a bold tote or earrings) add the fun.
All-White Outfit

White jeans + a white tank or blouse feels crisp, clean, and totally May-core. Layer gold jewelry for a little sparkle.
Gingham or Eyelet Dress

Lean into spring textures and prints. Eyelet and gingham are always a yes for May picnics, brunches, or garden parties.
🌿 Final Style Note
May outfits are all about that sweet balance — sunny, but still layerable.
You get to mix the freshness of spring with the ease of summer, and that means creativity, versatility, and so much style potential.
Whether you’re dressing up or keeping it casual, May is the month to let your wardrobe bloom 🌷✨