May brought the perfect mix of spring sunshine and transitional weather, and my wardrobe reflected just that—with a little bit of everything! From relaxed weekend looks to polished business casual outfits, I found myself reaching for pieces that were equal parts comfortable and put-together. In this post, I’m sharing my ten favorite outfits from the month—whether you’re looking for easy everyday style or something office-appropriate, you’ll find plenty of inspiration here.
My Ten Favorite Outfits of May
Lady Jacket Cardigan + Pink Pull On Pants + Bow Slingback Flats
Sweater- Amazon; pants- Nordstrom; shoes- ThredUp
This outfit has quickly become one of my favorites because it feels polished but still so comfortable. The tan and cream lady jacket sweater gives off that classic, put-together vibe without being stiff or overly formal. I love how it pairs with the pink linen-blend pants—they add just the right touch of soft color and keep things feeling fresh and light for spring.
And let’s talk about these neutral bow slingback shoes—so feminine and easy to wear, they pull the whole look together without overpowering it. They are one of my favorite Thred Up finds.
White Linen Blazer + Crochet Top + Navy Kick Flare Crop Pants + Silver Mary Janes
Blazer- option; top- option; pants- Gap; shoes- Walmart
This outfit is one I reach for when I want to look sharp but still feel light and breezy. The white linen blazer instantly adds structure and polish, but it’s so breathable—perfect for warmer days when I still want that tailored feel. I layered it over a crochet top for a bit of texture and a hint of femininity, and I love how it contrasts with the clean lines of the navy kick flare crop pants. These ponte pants are a wardrobe hero—they’re flattering, easy to move in, and hit just the right spot above the ankle to show off the silver Mary Janes. The metallic finish adds a little personality without being too loud. This look is equal parts modern, elegant, and fun—just the way I like my outfits.
Yellow V-neck Sweater + Cream Pants + Brown Loafers
Sweater- Old Navy; Pants- Old Navy; shoes Lifestride via Amazon
This outfit is a go-to for me when I want something simple, bright, and effortlessly put together. The yellow v-neck sweater adds such a cheerful pop of color without being too bold—it instantly lifts my mood and feels perfect for spring. I paired it with cream pants to keep the look light and clean, and the combo feels so fresh and easy. The brown loafers ground the outfit with a classic touch and make it ideal for days when I’m on the go but still want to look polished. It’s one of those looks that feels low-effort but looks totally intentional.
Navy Blazer + Navy Polo Sweater + White Pants+ Cognac Slingback Flats
Polo Sweater- Amazon; shoes- DSW
There’s something about a monochromatic navy look that always feels effortlessly chic—and this outfit is one I reach for when I want to feel sharp and confident. The navy blazer layered over a navy polo sweater creates a clean, streamlined base that’s classic but never boring. I love the contrast of the crisp white pants—they keep the outfit feeling fresh and modern. And the cognac slingback flats? They add just the right amount of warmth and polish, plus they’re incredibly comfortable.
Yellow Cropped Blazer + White Tank + Navy Pants + Neutral Mules
Blazer- Amazon; pants- similar; tank- similar; shoes- similar; necklace- Loft
This outfit is the perfect blend of bold and classic—and that’s exactly why I love it. The yellow cropped blazer brings such a fun pop of color and instantly brightens up the whole look. It’s structured but playful, and pairs beautifully with a crisp white tank for a clean, fresh base. I balanced it out with tailored navy pants for a polished feel, and slipped on neutral mules to keep things modern and comfortable. It’s an easy way to look pulled together without overthinking it—and it always gets compliments.
Pink Lady Jacket + White Sweater Tee + Taupe Pants + Cognac Slingback Flats
Jacket- Amazon; top- option; similar; pants- Quince; shoes- DSW
This outfit is one of my favorites when I want to feel feminine and polished without trying too hard. The pink lady jacket adds just the right amount of structure with a soft, classic touch—it’s pretty but still professional. I layered it over a simple white sweater tee for a clean, breathable base that works for warmer days. The taupe pants keep the look grounded and neutral, while the cognac slingback flats pull it all together with a timeless finish. It’s effortless, flattering, and perfect for everything from the office to weekend brunch.
Blue Blazer + Print Top + Navy Top + Cognac Slingback Flats
Blazer- similar; pants- BRF; shoes- DSW
This look is a great example of how I like to mix polish with personality. The blue blazer adds a crisp, structured layer that instantly elevates the outfit, while the printed top underneath brings a fun pop of pattern that keeps things interesting. I paired it with classic navy pants for a sleek, pulled-together feel, and finished the look with my go-to cognac slingback flats—they’re comfortable, stylish, and go with just about everything. It’s an easy outfit that feels professional but not boring—perfect for when I want to feel confident and put-together all day.
Denim Shirt Dress + Fisherman Sandals
Dress- Target; shoes- Old Navy; tote- Amazon
This denim shirt dress is one of those effortless pieces I reach for when I want to look put-together with zero fuss. The fit is relaxed but flattering, and I love how easy it is to dress up or down. Paired with my fisherman sandals, it gives off that casual, cool vibe that’s perfect for warm days on the go. This outfit always feels stylish and comfortable—and best of all, it takes just minutes to throw on and walk out the door feeling confident.
See also How to Style a Denim Dress at Any Age: 5 Easy Spring Outfit Ideas
Striped Linen Button Up + Denim Midi Skirt+ Cognac Slide Sandals
Shirt- Old Navy; skirt Banana Republic; shoes- Amazon; tote- Amazon
This outfit is classic with a touch of coastal charm. The striped linen button-up is light, airy, and gives off that effortless, pulled-together vibe I love. I paired it with a denim midi skirt for a bit of structure and a timeless feel—it’s flattering, easy to wear, and adds just the right amount of polish. The cognac slide sandals finish the look with a warm, relaxed touch that ties everything together. It’s the kind of outfit that works for just about anything and makes me feel stylish without overthinking it.
Striped Linen Blend Popover + Linen Blend Pants + Cognac Slide Sandals
Top- Old Navy; pants- Old Navy; shoes- Amazon; tote- Amazon
This outfit is all about ease and understated style—just the way I like to dress in the warmer months. The striped linen-blend popover is lightweight and breathable, with a relaxed fit that still feels refined. I paired it with matching linen-blend pants for a coordinated, effortless look that’s as comfortable as it is chic. The cognac slide sandals add that final touch of laid-back polish and warmth, making this the perfect outfit for casual days when I still want to feel put-together. It’s breezy, flattering, and ideal for everything from coffee runs to weekend outings.
Each of these outfits from May has earned a spot in my favorites for a reason—they strike that ideal balance between comfort, confidence, and style. Whether I was dressing for a casual day out or a more polished office setting, these looks made getting dressed feel effortless and fun. I hope they give you some inspiration for mixing colors, textures, and timeless pieces in your own wardrobe as we head into the heart of summer.
